JP7370587B2 - 有機化合物の製造方法およびコリネ型細菌 - Google Patents
有機化合物の製造方法およびコリネ型細菌 Download PDFInfo
- Publication number
- JP7370587B2 JP7370587B2 JP2020073446A JP2020073446A JP7370587B2 JP 7370587 B2 JP7370587 B2 JP 7370587B2 JP 2020073446 A JP2020073446 A JP 2020073446A JP 2020073446 A JP2020073446 A JP 2020073446A JP 7370587 B2 JP7370587 B2 JP 7370587B2
- Authority
- JP
- Japan
- Prior art keywords
- gene
- protein
- acid
- seq
- carbonyl compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000004519 manufacturing process Methods 0.000 title description 283
- 241000186031 Corynebacteriaceae Species 0.000 title description 9
- 150000002894 organic compounds Chemical class 0.000 title description 5
- 108090000623 proteins and genes Proteins 0.000 claims description 826
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 366
- 150000001413 amino acids Chemical class 0.000 claims description 365
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 352
- 102000004169 proteins and genes Human genes 0.000 claims description 326
- 150000004716 alpha keto acids Chemical class 0.000 claims description 223
- 229940107700 pyruvic acid Drugs 0.000 claims description 183
- 238000005575 aldol reaction Methods 0.000 claims description 178
- 230000000694 effects Effects 0.000 claims description 171
- 238000006722 reduction reaction Methods 0.000 claims description 44
- 150000001299 aldehydes Chemical class 0.000 claims description 37
- 238000006114 decarboxylation reaction Methods 0.000 claims description 26
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims description 25
- 241000186254 coryneform bacterium Species 0.000 claims description 17
- 125000003275 alpha amino acid group Chemical group 0.000 claims 14
- 235000018102 proteins Nutrition 0.000 description 315
- 239000000243 solution Substances 0.000 description 256
- 238000000034 method Methods 0.000 description 230
- 239000001257 hydrogen Substances 0.000 description 210
- 229910052739 hydrogen Inorganic materials 0.000 description 210
- 229940024606 amino acid Drugs 0.000 description 130
- 235000001014 amino acid Nutrition 0.000 description 130
- 244000005700 microbiome Species 0.000 description 130
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 123
- 150000001875 compounds Chemical class 0.000 description 119
- 102000004190 Enzymes Human genes 0.000 description 111
- 108090000790 Enzymes Proteins 0.000 description 111
- 229940088598 enzyme Drugs 0.000 description 111
- 150000002431 hydrogen Chemical class 0.000 description 91
- 239000002253 acid Substances 0.000 description 87
- 238000012258 culturing Methods 0.000 description 81
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 64
- 238000006243 chemical reaction Methods 0.000 description 62
- 238000006268 reductive amination reaction Methods 0.000 description 57
- 241000588724 Escherichia coli Species 0.000 description 56
- 108010068561 Fructose-Bisphosphate Aldolase Proteins 0.000 description 53
- 102000001390 Fructose-Bisphosphate Aldolase Human genes 0.000 description 53
- 229940076788 pyruvate Drugs 0.000 description 51
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 50
- 150000000185 1,3-diols Chemical class 0.000 description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 42
- 108010028658 Leucine Dehydrogenase Proteins 0.000 description 39
- -1 feed Substances 0.000 description 39
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 39
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 38
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 38
- 101710100604 Valine dehydrogenase Proteins 0.000 description 38
- 239000008103 glucose Substances 0.000 description 38
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 38
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 37
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 37
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 37
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 34
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 33
- 125000000217 alkyl group Chemical group 0.000 description 33
- 125000004432 carbon atom Chemical group C* 0.000 description 33
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 32
- 235000013922 glutamic acid Nutrition 0.000 description 32
- 239000004220 glutamic acid Substances 0.000 description 32
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 32
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 30
- 101150054405 hpcH gene Proteins 0.000 description 28
- 239000013600 plasmid vector Substances 0.000 description 28
- 230000035755 proliferation Effects 0.000 description 28
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 26
- 230000009466 transformation Effects 0.000 description 26
- 239000001963 growth medium Substances 0.000 description 24
- 238000006467 substitution reaction Methods 0.000 description 24
- 239000013598 vector Substances 0.000 description 23
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- 150000001720 carbohydrates Chemical class 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 235000000346 sugar Nutrition 0.000 description 21
- 238000012217 deletion Methods 0.000 description 20
- 230000037430 deletion Effects 0.000 description 20
- 150000008163 sugars Chemical class 0.000 description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
- 230000008569 process Effects 0.000 description 19
- 241000894007 species Species 0.000 description 19
- 108020004414 DNA Proteins 0.000 description 18
- 238000006911 enzymatic reaction Methods 0.000 description 18
- 101710088194 Dehydrogenase Proteins 0.000 description 17
- 150000007513 acids Chemical class 0.000 description 17
- 239000000872 buffer Substances 0.000 description 17
- HSJKGGMUJITCBW-UHFFFAOYSA-N beta-hydroxybutyraldehyde Natural products CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 16
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 16
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 15
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 15
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 14
- 238000002425 crystallisation Methods 0.000 description 14
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 14
- 239000001301 oxygen Substances 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- PUWWONYMIXRVQF-UHFFFAOYSA-N 4-Hydroxy-2-oxobutanoic acid Chemical compound OCCC(=O)C(O)=O PUWWONYMIXRVQF-UHFFFAOYSA-N 0.000 description 13
- HFKQINMYQUXOCH-UHFFFAOYSA-N 4-hydroxy-2-oxopentanoic acid Chemical compound CC(O)CC(=O)C(O)=O HFKQINMYQUXOCH-UHFFFAOYSA-N 0.000 description 13
- 241000186226 Corynebacterium glutamicum Species 0.000 description 13
- 101150051452 bphI gene Proteins 0.000 description 13
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 13
- 230000002759 chromosomal effect Effects 0.000 description 13
- 101150002067 dgoA gene Proteins 0.000 description 13
- 150000002772 monosaccharides Chemical class 0.000 description 13
- 238000011084 recovery Methods 0.000 description 13
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 12
- 241000589776 Pseudomonas putida Species 0.000 description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 12
- 101150087346 mhpE gene Proteins 0.000 description 12
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 12
- 241000894006 Bacteria Species 0.000 description 11
- 101150053890 EDA gene Proteins 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 230000007423 decrease Effects 0.000 description 11
- 101150022753 galc gene Proteins 0.000 description 11
- 101150019000 garL gene Proteins 0.000 description 11
- 101150074166 nanA gene Proteins 0.000 description 11
- 101150058184 rhmA gene Proteins 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 239000004473 Threonine Substances 0.000 description 10
- 230000009471 action Effects 0.000 description 10
- 239000003638 chemical reducing agent Substances 0.000 description 10
- 238000010276 construction Methods 0.000 description 10
- 150000004676 glycans Chemical class 0.000 description 10
- 101150080950 mdlC gene Proteins 0.000 description 10
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 10
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 10
- 229920001282 polysaccharide Polymers 0.000 description 10
- 239000005017 polysaccharide Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 229960002898 threonine Drugs 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 101100106373 Escherichia coli (strain K12) yjhH gene Proteins 0.000 description 9
- 101100132713 Escherichia coli O6:H1 (strain CFT073 / ATCC 700928 / UPEC) nanA1 gene Proteins 0.000 description 9
- 101100451349 Mycobacterium tuberculosis (strain ATCC 25177 / H37Ra) hsaF gene Proteins 0.000 description 9
- 101100297425 Nocardioides sp. (strain KP7) phdJ gene Proteins 0.000 description 9
- 244000057717 Streptococcus lactis Species 0.000 description 9
- 235000014897 Streptococcus lactis Nutrition 0.000 description 9
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 9
- 238000010586 diagram Methods 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 230000000813 microbial effect Effects 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 9
- 108700026220 vif Genes Proteins 0.000 description 9
- 108090000489 Carboxy-Lyases Proteins 0.000 description 8
- 101100215028 Escherichia coli (strain K12) mhpF gene Proteins 0.000 description 8
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 8
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 8
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
- 101150070760 cgs1 gene Proteins 0.000 description 8
- 210000000349 chromosome Anatomy 0.000 description 8
- 101150061843 dhaT gene Proteins 0.000 description 8
- 101150041530 ldha gene Proteins 0.000 description 8
- 229960004452 methionine Drugs 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 7
- 241000186216 Corynebacterium Species 0.000 description 7
- 101100105449 Escherichia coli (strain K12) yagE gene Proteins 0.000 description 7
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 7
- 101100342797 Geobacillus stearothermophilus ldh gene Proteins 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000000470 constituent Substances 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 239000003456 ion exchange resin Substances 0.000 description 7
- 229920003303 ion-exchange polymer Polymers 0.000 description 7
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 7
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 7
- 229930182817 methionine Natural products 0.000 description 7
- 239000007800 oxidant agent Substances 0.000 description 7
- 238000000638 solvent extraction Methods 0.000 description 7
- 238000001179 sorption measurement Methods 0.000 description 7
- OVPRPPOVAXRCED-WVZVXSGGSA-N 2-dehydro-3-deoxy-6-phospho-D-gluconic acid Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)CC(=O)C(O)=O OVPRPPOVAXRCED-WVZVXSGGSA-N 0.000 description 6
- 108030003135 2-dehydro-3-deoxy-D-pentonate aldolases Proteins 0.000 description 6
- 108010016941 2-keto-3-deoxy-D-glucarate aldolase Proteins 0.000 description 6
- DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 6
- 108030003145 3-deoxy-D-manno-octulosonate aldolases Proteins 0.000 description 6
- 108030003175 4-(2-carboxyphenyl)-2-oxobut-3-enoate aldolases Proteins 0.000 description 6
- 108030003208 4-hydroxy-2-oxoheptanedioate aldolases Proteins 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 241000219194 Arabidopsis Species 0.000 description 6
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 6
- 229930091371 Fructose Natural products 0.000 description 6
- 239000005715 Fructose Substances 0.000 description 6
- 102000000893 Glutamate/phenylalanine/leucine/valine dehydrogenases Human genes 0.000 description 6
- 108050007901 Glutamate/phenylalanine/leucine/valine dehydrogenases Proteins 0.000 description 6
- WXSKVKPSMAHCSG-REOHCLBHSA-N L-4-hydroxy-2-oxoglutaric acid Chemical compound OC(=O)[C@@H](O)CC(=O)C(O)=O WXSKVKPSMAHCSG-REOHCLBHSA-N 0.000 description 6
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 6
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 6
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- 101100398785 Streptococcus agalactiae serotype V (strain ATCC BAA-611 / 2603 V/R) ldhD gene Proteins 0.000 description 6
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
- 229930006000 Sucrose Natural products 0.000 description 6
- 101100386830 Zymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4) ddh gene Proteins 0.000 description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 150000002016 disaccharides Chemical class 0.000 description 6
- 101150026107 ldh1 gene Proteins 0.000 description 6
- 229910000357 manganese(II) sulfate Inorganic materials 0.000 description 6
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 6
- 235000019796 monopotassium phosphate Nutrition 0.000 description 6
- 229960002446 octanoic acid Drugs 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 230000037361 pathway Effects 0.000 description 6
- 108010038136 phospho-2-keto-3-deoxy-gluconate aldolase Proteins 0.000 description 6
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000005720 sucrose Substances 0.000 description 6
- UFYGCFHQAXXBCF-UHFFFAOYSA-N 2,4-dihydroxybutanoic acid Chemical compound OCCC(O)C(O)=O UFYGCFHQAXXBCF-UHFFFAOYSA-N 0.000 description 5
- YRWAMSXHYBBHFL-UHFFFAOYSA-N 4-hydroxy-4-methyl-2-oxoglutaric acid Chemical compound OC(=O)C(O)(C)CC(=O)C(O)=O YRWAMSXHYBBHFL-UHFFFAOYSA-N 0.000 description 5
- 101000950981 Bacillus subtilis (strain 168) Catabolic NAD-specific glutamate dehydrogenase RocG Proteins 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 241000588747 Klebsiella pneumoniae Species 0.000 description 5
- 241000192041 Micrococcus Species 0.000 description 5
- 241000187580 Nocardioides Species 0.000 description 5
- 108030006096 S-(hydroxymethyl)mycothiol dehydrogenases Proteins 0.000 description 5
- 108090000340 Transaminases Proteins 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 5
- 108010081577 aldehyde dehydrogenase (NAD(P)+) Proteins 0.000 description 5
- 239000012670 alkaline solution Substances 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 210000000805 cytoplasm Anatomy 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 230000034659 glycolysis Effects 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 150000007522 mineralic acids Chemical class 0.000 description 5
- 108010078226 phenylalanine oxidase Proteins 0.000 description 5
- 238000011426 transformation method Methods 0.000 description 5
- 108030003207 2-dehydro-3-deoxy-D-gluconate aldolases Proteins 0.000 description 4
- 108030003205 2-keto-3-deoxy-L-rhamnonate aldolases Proteins 0.000 description 4
- 108010071258 4-hydroxy-2-oxoglutarate aldolase Proteins 0.000 description 4
- 108010021809 Alcohol dehydrogenase Proteins 0.000 description 4
- 102000007698 Alcohol dehydrogenase Human genes 0.000 description 4
- 102000003677 Aldehyde-Lyases Human genes 0.000 description 4
- 108090000072 Aldehyde-Lyases Proteins 0.000 description 4
- 241000193408 Bacillus badius Species 0.000 description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- 108020005199 Dehydrogenases Proteins 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 4
- 241001509383 Paraburkholderia xenovorans Species 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 4
- 102000054767 gene variant Human genes 0.000 description 4
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 229910052816 inorganic phosphate Inorganic materials 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 238000000691 measurement method Methods 0.000 description 4
- 239000002207 metabolite Substances 0.000 description 4
- 238000007833 oxidative deamination reaction Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000001131 transforming effect Effects 0.000 description 4
- 108010011958 1,3-propanediol dehydrogenase Proteins 0.000 description 3
- CXVPLYZTFFPNOU-UHFFFAOYSA-N 4-hydroxy-2-oxoheptanoic acid Chemical compound OC(CC(C(=O)O)=O)CCC CXVPLYZTFFPNOU-UHFFFAOYSA-N 0.000 description 3
- ALFQPWXBAWHVDP-UHFFFAOYSA-N 4-hydroxy-2-oxohexanoic acid Chemical compound CCC(O)CC(=O)C(O)=O ALFQPWXBAWHVDP-UHFFFAOYSA-N 0.000 description 3
- QDXJQNIRIVKJCB-UHFFFAOYSA-N 4-hydroxy-2-oxooctanoic acid Chemical compound CCCCC(O)CC(=O)C(O)=O QDXJQNIRIVKJCB-UHFFFAOYSA-N 0.000 description 3
- IUCVHWOEHKADHP-UHFFFAOYSA-N 4-hydroxy-4-methyl-2-oxopentanoic acid Chemical compound CC(C)(O)CC(=O)C(O)=O IUCVHWOEHKADHP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108010000700 Acetolactate synthase Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 102000016901 Glutamate dehydrogenase Human genes 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXDNYOANAXWZHG-VKHMYHEASA-N O-phospho-L-homoserine Chemical compound OC(=O)[C@@H](N)CCOP(O)(O)=O FXDNYOANAXWZHG-VKHMYHEASA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 102100033451 Thyroid hormone receptor beta Human genes 0.000 description 3
- 102000003929 Transaminases Human genes 0.000 description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical compound CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 3
- 241000319304 [Brevibacterium] flavum Species 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
- 125000000539 amino acid group Chemical group 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000404 glutamine group Chemical class N[C@@H](CCC(N)=O)C(=O)* 0.000 description 3
- 108010071598 homoserine kinase Proteins 0.000 description 3
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- 230000035772 mutation Effects 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- HUHVCDMWCABQML-UHFFFAOYSA-N 2-amino-4-hydroxyheptanoic acid Chemical compound CCCC(O)CC(N)C(O)=O HUHVCDMWCABQML-UHFFFAOYSA-N 0.000 description 2
- DMCRWAJLYOEMSK-UHFFFAOYSA-N 2-amino-4-hydroxyhexanoic acid Chemical compound CCC(O)CC(N)C(O)=O DMCRWAJLYOEMSK-UHFFFAOYSA-N 0.000 description 2
- GKYXBQLORQSZRP-UHFFFAOYSA-N 2-amino-4-hydroxyoctanoic acid Chemical compound CCCCC(O)CC(N)C(O)=O GKYXBQLORQSZRP-UHFFFAOYSA-N 0.000 description 2
- SBRVJFMQKPUAGQ-UHFFFAOYSA-N 2-amino-4-hydroxypentanoic acid Chemical compound CC(O)CC(N)C(O)=O SBRVJFMQKPUAGQ-UHFFFAOYSA-N 0.000 description 2
- SWMDCXYSYSMCJM-UHFFFAOYSA-N 2-aminopentanethioic s-acid Chemical compound CCCC(N)C(S)=O SWMDCXYSYSMCJM-UHFFFAOYSA-N 0.000 description 2
- KEEQSWOXTDTQJV-UHFFFAOYSA-N 4-hydroxyleucine Chemical compound CC(C)(O)CC(N)C(O)=O KEEQSWOXTDTQJV-UHFFFAOYSA-N 0.000 description 2
- 101100383400 Arabidopsis thaliana CGS1 gene Proteins 0.000 description 2
- 241000186063 Arthrobacter Species 0.000 description 2
- 241000193755 Bacillus cereus Species 0.000 description 2
- 108010071778 Benzoylformate decarboxylase Proteins 0.000 description 2
- 241000186146 Brevibacterium Species 0.000 description 2
- 241000186145 Corynebacterium ammoniagenes Species 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000626621 Geobacillus Species 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000186604 Lactobacillus reuteri Species 0.000 description 2
- 241000193386 Lysinibacillus sphaericus Species 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 108010061618 O-succinylhomoserine (thiol)-lyase Proteins 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 108010011939 Pyruvate Decarboxylase Proteins 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000187747 Streptomyces Species 0.000 description 2
- 241000187438 Streptomyces fradiae Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 241000588902 Zymomonas mobilis Species 0.000 description 2
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000010170 biological method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000013592 cell lysate Substances 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000012531 culture fluid Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- HTXVEEVTGGCUNC-UHFFFAOYSA-N heptane-1,3-diol Chemical compound CCCCC(O)CCO HTXVEEVTGGCUNC-UHFFFAOYSA-N 0.000 description 2
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 108010072869 indolepyruvate decarboxylase Proteins 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229940001882 lactobacillus reuteri Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- MQBCDKMPXVYCGO-FQBKTPCVSA-N mycothiol Chemical compound CC(=O)N[C@@H](CS)C(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1O MQBCDKMPXVYCGO-FQBKTPCVSA-N 0.000 description 2
- MQBCDKMPXVYCGO-UHFFFAOYSA-N mycothiol Natural products CC(=O)NC(CS)C(=O)NC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(O)C1O MQBCDKMPXVYCGO-UHFFFAOYSA-N 0.000 description 2
- 108010074581 mycothiol Proteins 0.000 description 2
- 101150082883 phdJ gene Proteins 0.000 description 2
- 108010025593 phenylalanine (histidine) aminotransferase Proteins 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- ZNJHFNUEQDVFCJ-UHFFFAOYSA-M sodium;2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid;hydroxide Chemical compound [OH-].[Na+].OCCN1CCN(CCS(O)(=O)=O)CC1 ZNJHFNUEQDVFCJ-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229960003495 thiamine Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940011671 vitamin b6 Drugs 0.000 description 2
- 101150003537 yjhH gene Proteins 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- LGQKSQQRKHFMLI-SJYYZXOBSA-N (2s,3r,4s,5r)-2-[(3r,4r,5r,6r)-4,5,6-trihydroxyoxan-3-yl]oxyoxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)CO[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)OC1 LGQKSQQRKHFMLI-SJYYZXOBSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- SEKOUJKSJKLRIO-UHFFFAOYSA-N 2,4-dihydroxy-4-methylpentanoic acid Chemical compound CC(C)(O)CC(O)C(O)=O SEKOUJKSJKLRIO-UHFFFAOYSA-N 0.000 description 1
- MVZWTLPFQQIPEY-UHFFFAOYSA-N 2,4-dihydroxyheptanoic acid Chemical compound CCCC(O)CC(O)C(O)=O MVZWTLPFQQIPEY-UHFFFAOYSA-N 0.000 description 1
- HMGGSVFAGUJIAP-UHFFFAOYSA-N 2,4-dihydroxyhexanoic acid Chemical compound CCC(O)CC(O)C(O)=O HMGGSVFAGUJIAP-UHFFFAOYSA-N 0.000 description 1
- FJZZGPQFHSWNST-UHFFFAOYSA-N 2,4-dihydroxyoctanoic acid Chemical compound OC(C(=O)O)CC(CCCC)O FJZZGPQFHSWNST-UHFFFAOYSA-N 0.000 description 1
- VGAFMEAWKVZZIM-UHFFFAOYSA-N 2,4-dihydroxypentanoic acid Chemical compound CC(O)CC(O)C(O)=O VGAFMEAWKVZZIM-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- CWGINJMKLZNZRH-UHFFFAOYSA-N 2-amino-4,4-dimethylpentanethioic S-acid Chemical compound CC(C)(C)CC(C(=O)S)N CWGINJMKLZNZRH-UHFFFAOYSA-N 0.000 description 1
- IYELTAZRNBZDSO-UHFFFAOYSA-N 2-amino-4-methylheptanethioic S-acid Chemical compound CCCC(C)CC(C(=O)S)N IYELTAZRNBZDSO-UHFFFAOYSA-N 0.000 description 1
- UFEOEGGBQJHNNS-UHFFFAOYSA-N 2-amino-4-methylhexanethioic S-acid Chemical compound CCC(C)CC(C(=O)S)N UFEOEGGBQJHNNS-UHFFFAOYSA-N 0.000 description 1
- CSEYFMVRSPYRNJ-UHFFFAOYSA-N 2-amino-4-methyloctanethioic S-acid Chemical compound CCCCC(C)CC(C(=O)S)N CSEYFMVRSPYRNJ-UHFFFAOYSA-N 0.000 description 1
- DHTNOUONHCPNOQ-UHFFFAOYSA-N 2-amino-4-methylpentanethioic s-acid Chemical compound CC(C)CC(N)C(S)=O DHTNOUONHCPNOQ-UHFFFAOYSA-N 0.000 description 1
- FXFBPKDQLDOIRG-UHFFFAOYSA-N 3-hydroxy-3-methylbutanal Chemical compound CC(C)(O)CC=O FXFBPKDQLDOIRG-UHFFFAOYSA-N 0.000 description 1
- WRWLNLBWBJEUPI-UHFFFAOYSA-N 3-hydroxypentanal Chemical compound CCC(O)CC=O WRWLNLBWBJEUPI-UHFFFAOYSA-N 0.000 description 1
- XPFCZYUVICHKDS-UHFFFAOYSA-N 3-methylbutane-1,3-diol Chemical compound CC(C)(O)CCO XPFCZYUVICHKDS-UHFFFAOYSA-N 0.000 description 1
- LGQKSQQRKHFMLI-UHFFFAOYSA-N 4-O-beta-D-xylopyranosyl-beta-D-xylopyranose Natural products OC1C(O)C(O)COC1OC1C(O)C(O)C(O)OC1 LGQKSQQRKHFMLI-UHFFFAOYSA-N 0.000 description 1
- DCBLTYZAUIEBCX-UHFFFAOYSA-N 4-methylpentane-1,3-diol Chemical compound CC(C)C(O)CCO DCBLTYZAUIEBCX-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000219195 Arabidopsis thaliana Species 0.000 description 1
- 241000186074 Arthrobacter globiformis Species 0.000 description 1
- 101100231599 Azotobacter vinelandii (strain DJ / ATCC BAA-1303) mphE gene Proteins 0.000 description 1
- 241001453380 Burkholderia Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- 241000909293 Corynebacterium alkanolyticum Species 0.000 description 1
- 241001644925 Corynebacterium efficiens Species 0.000 description 1
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 1
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- SQNRKWHRVIAKLP-UHFFFAOYSA-N D-xylobiose Natural products O=CC(O)C(O)C(CO)OC1OCC(O)C(O)C1O SQNRKWHRVIAKLP-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- 241000191948 Kocuria rosea Species 0.000 description 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
- 229930195722 L-methionine Natural products 0.000 description 1
- 125000000510 L-tryptophano group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[C@@]([H])(C(O[H])=O)N([H])[*])C2=C1[H] 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 240000003433 Miscanthus floridulus Species 0.000 description 1
- 241000186366 Mycobacterium bovis Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241001495390 Nocardioides sp. Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001520808 Panicum virgatum Species 0.000 description 1
- 244000130556 Pennisetum purpureum Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 101100462488 Phlebiopsis gigantea p2ox gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 108010053763 Pyruvate Carboxylase Proteins 0.000 description 1
- 102100039895 Pyruvate carboxylase, mitochondrial Human genes 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- 108010006873 Threonine Dehydratase Proteins 0.000 description 1
- 102000006843 Threonine synthase Human genes 0.000 description 1
- 108010022394 Threonine synthase Proteins 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000607365 Vibrio natriegens Species 0.000 description 1
- 229930003451 Vitamin B1 Natural products 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 101150014383 adhE gene Proteins 0.000 description 1
- 241001148470 aerobic bacillus Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000002154 agricultural waste Substances 0.000 description 1
- 101150001823 alaA gene Proteins 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 101150049512 ald gene Proteins 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 101150106154 bphJ gene Proteins 0.000 description 1
- 229960003563 calcium carbonate Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 101150033780 ilvB gene Proteins 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 101150024975 mhpF gene Proteins 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- GUUBJKMBDULZTE-UHFFFAOYSA-M potassium;2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid;hydroxide Chemical compound [OH-].[K+].OCCN1CCN(CCS(O)(=O)=O)CC1 GUUBJKMBDULZTE-UHFFFAOYSA-M 0.000 description 1
- 101150060030 poxB gene Proteins 0.000 description 1
- 101150023641 ppc gene Proteins 0.000 description 1
- 230000004853 protein function Effects 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 101150096049 pyc gene Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 1
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 description 1
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
- 229960001327 pyridoxal phosphate Drugs 0.000 description 1
- 235000008160 pyridoxine Nutrition 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- AIJULSRZWUXGPQ-UHFFFAOYSA-N pyruvic aldehyde Natural products CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 1
- 108700022487 rRNA Genes Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940102127 rubidium chloride Drugs 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- CSRCBLMBBOJYEX-UHFFFAOYSA-M sodium;2-morpholin-4-ylethanesulfonic acid;hydroxide Chemical compound [OH-].[Na+].OS(=O)(=O)CCN1CCOCC1 CSRCBLMBBOJYEX-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010907 stover Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 229960002363 thiamine pyrophosphate Drugs 0.000 description 1
- 235000008170 thiamine pyrophosphate Nutrition 0.000 description 1
- 239000011678 thiamine pyrophosphate Substances 0.000 description 1
- YXVCLPJQTZXJLH-UHFFFAOYSA-N thiamine(1+) diphosphate chloride Chemical compound [Cl-].CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N YXVCLPJQTZXJLH-UHFFFAOYSA-N 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 235000010374 vitamin B1 Nutrition 0.000 description 1
- 239000011691 vitamin B1 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
Images
Landscapes
- Enzymes And Modification Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020073446A JP7370587B2 (ja) | 2018-10-30 | 2020-04-16 | 有機化合物の製造方法およびコリネ型細菌 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019551409A JP6894650B2 (ja) | 2018-10-30 | 2018-10-30 | 有機化合物の製造方法およびコリネ型細菌 |
| JP2020073446A JP7370587B2 (ja) | 2018-10-30 | 2020-04-16 | 有機化合物の製造方法およびコリネ型細菌 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019551409A Division JP6894650B2 (ja) | 2018-10-30 | 2018-10-30 | 有機化合物の製造方法およびコリネ型細菌 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020182449A JP2020182449A (ja) | 2020-11-12 |
| JP2020182449A5 JP2020182449A5 (https=) | 2021-11-11 |
| JP7370587B2 true JP7370587B2 (ja) | 2023-10-30 |
Family
ID=73044164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020073446A Active JP7370587B2 (ja) | 2018-10-30 | 2020-04-16 | 有機化合物の製造方法およびコリネ型細菌 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP7370587B2 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112391363B (zh) * | 2021-01-21 | 2021-04-06 | 凯莱英生命科学技术(天津)有限公司 | 氨基酸脱氢酶突变体及其应用 |
| CN116042496A (zh) * | 2022-09-22 | 2023-05-02 | 河南巨龙生物工程股份有限公司 | 发酵生产l-瓜氨酸的大肠杆菌基因工程菌、构建方法和应用 |
| CN120665964A (zh) * | 2024-03-19 | 2025-09-19 | 摩珈(上海)生物科技有限公司 | 2-氨基-4-甲硫基-丁酸或2-羟基-4-甲硫基-丁酸的制备方法 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014521365A (ja) | 2011-08-19 | 2014-08-28 | ジェノマティカ・インコーポレイテッド | ２，４−ペンタジエノエート、ブタジエン、プロピレン、１，３−ブタンジオールおよび関連アルコールを生成するための微生物および方法 |
| US20160257976A1 (en) | 2013-05-06 | 2016-09-08 | Korea Research Institute Of Bioscience And Biotechnology | Biological Synthesis of 6-Aminocaproic Acid and Transgenic Microorganism Therefor |
| WO2017198717A1 (en) | 2016-05-18 | 2017-11-23 | Consejo Superior De Investigaciones Científicas | Fusion proteins comprising an aldolase enzyme joined to a maltose binding protein |
| US20180044684A1 (en) | 2010-11-22 | 2018-02-15 | Cargill, Incorporated | Compositions and methods for 3-hydroxypropionic acid production |
| WO2018067458A1 (en) | 2016-10-03 | 2018-04-12 | The Regents Of The University Of California | Engineered microorganisms for production of commodity chemicals and cellular biomass |
| CN108285886A (zh) | 2018-01-30 | 2018-07-17 | 江南大学 | 重组枯草芽孢杆菌全细胞转化生产n-乙酰神经氨酸的方法 |
-
2020
- 2020-04-16 JP JP2020073446A patent/JP7370587B2/ja active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180044684A1 (en) | 2010-11-22 | 2018-02-15 | Cargill, Incorporated | Compositions and methods for 3-hydroxypropionic acid production |
| JP2014521365A (ja) | 2011-08-19 | 2014-08-28 | ジェノマティカ・インコーポレイテッド | ２，４−ペンタジエノエート、ブタジエン、プロピレン、１，３−ブタンジオールおよび関連アルコールを生成するための微生物および方法 |
| US20160257976A1 (en) | 2013-05-06 | 2016-09-08 | Korea Research Institute Of Bioscience And Biotechnology | Biological Synthesis of 6-Aminocaproic Acid and Transgenic Microorganism Therefor |
| WO2017198717A1 (en) | 2016-05-18 | 2017-11-23 | Consejo Superior De Investigaciones Científicas | Fusion proteins comprising an aldolase enzyme joined to a maltose binding protein |
| WO2018067458A1 (en) | 2016-10-03 | 2018-04-12 | The Regents Of The University Of California | Engineered microorganisms for production of commodity chemicals and cellular biomass |
| CN108285886A (zh) | 2018-01-30 | 2018-07-17 | 江南大学 | 重组枯草芽孢杆菌全细胞转化生产n-乙酰神经氨酸的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2020182449A (ja) | 2020-11-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6894650B2 (ja) | 有機化合物の製造方法およびコリネ型細菌 | |
| JP5774493B2 (ja) | ジオールの生産方法 | |
| JP6862349B2 (ja) | 発酵経路を経由するフラックスの増大を示す組み換え微生物体 | |
| AU2013215706B2 (en) | Recombinant microorganisms and methods of use thereof | |
| CN106459958B (zh) | 使高活性突变型酶高表达的棒状细菌转化体及使用它的4-羟基苯甲酸或其盐的制造方法 | |
| CN109890960B (zh) | 用于生产醛的方法 | |
| JP7370587B2 (ja) | 有機化合物の製造方法およびコリネ型細菌 | |
| CN101437949A (zh) | 利用辅酶再生进行的羟基羧酸类的生产方法 | |
| TW201005094A (en) | Polypeptide having glyoxalase III activity, polynucleotide encoding the same and uses thereof | |
| JP2017534268A (ja) | 有用産物の生産のための改変微生物および方法 | |
| CN110234768B (zh) | 用于产生乙醇酸和/或乙醛酸的方法和微生物 | |
| KR101521045B1 (ko) | 유기산을 생산하기 위한 재조합 미생물유기체 | |
| JP2013537429A (ja) | 改変微生物による改良されたグリコール酸発酵生産 | |
| EP3140412A1 (en) | Genetically modified microorganism for improved production of fine chemicals on sucrose | |
| JP6668577B1 (ja) | １，３−プロパンジオールの製造方法 | |
| JP5698655B2 (ja) | コリネ型細菌形質転換体及びそれを用いるイソブタノールの製造方法 | |
| CN113260706A (zh) | 棒状细菌转化体以及使用其的2-苯基乙醇的制造方法 | |
| KR102149044B1 (ko) | 2-히드록시 감마 부티로락톤 또는 2,4-디히드록시-부티레이트 의 제조 방법 | |
| EP2872639A2 (en) | A microorganism modified for the production of 1,3-propanediol | |
| US20140099676A1 (en) | Microorganisms and methods for producing acrylate and other products from homoserine | |
| EP3470512A1 (en) | Mutant phosphoserine aminotransferase for the conversion of homoserine into 4-hydroxy-2-ketobutyrate | |
| KR20190088648A (ko) | 에탄올에서 부탄디올의 생산방법 | |
| CN106536543B (zh) | 产生(s)-乳酸的嗜热细菌的遗传修饰 | |
| JP2021524262A (ja) | コリネ型細菌由来のＤ−キシロースデヒドロゲナーゼおよびＤ−キシロネートの生産（Ｈｅｒｓｔｅｌｌｕｎｇ）方法 | |
| EP2930244A1 (en) | Microorganisms and methods for producing acrylate and other products from homoserine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210928 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20210928 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220823 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230117 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20230214 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230315 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230613 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230719 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20230912 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20231011 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 7370587 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |