CA1217158A - Enzymatic synthesis of l-serine - Google Patents
Enzymatic synthesis of l-serineInfo
- Publication number
- CA1217158A CA1217158A CA000441483A CA441483A CA1217158A CA 1217158 A CA1217158 A CA 1217158A CA 000441483 A CA000441483 A CA 000441483A CA 441483 A CA441483 A CA 441483A CA 1217158 A CA1217158 A CA 1217158A
- Authority
- CA
- Canada
- Prior art keywords
- serine
- enzyme
- droxymethyltransferase
- tetrahydrofolate
- reaction
- 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.)
- Expired
Links
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 title claims abstract description 83
- 238000003786 synthesis reaction Methods 0.000 title description 7
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 230000002255 enzymatic effect Effects 0.000 title description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 66
- 229960001153 serine Drugs 0.000 claims abstract description 53
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000004471 Glycine Substances 0.000 claims abstract description 25
- 239000005460 tetrahydrofolate Substances 0.000 claims abstract description 17
- MSTNYGQPCMXVAQ-RYUDHWBXSA-N (6S)-5,6,7,8-tetrahydrofolic acid Chemical compound C([C@H]1CNC=2N=C(NC(=O)C=2N1)N)NC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 MSTNYGQPCMXVAQ-RYUDHWBXSA-N 0.000 claims abstract description 16
- 108010043428 Glycine hydroxymethyltransferase Proteins 0.000 claims abstract description 15
- 230000002210 biocatalytic effect Effects 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 54
- 102000004190 Enzymes Human genes 0.000 claims description 40
- 108090000790 Enzymes Proteins 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 28
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 24
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 claims description 19
- 101710084636 Serine hydroxymethyltransferase Proteins 0.000 claims description 16
- 102100021225 Serine hydroxymethyltransferase, cytosolic Human genes 0.000 claims description 16
- 101710099809 Serine hydroxymethyltransferase, cytosolic Proteins 0.000 claims description 16
- 101710087362 Serine hydroxymethyltransferase, mitochondrial Proteins 0.000 claims description 16
- 239000013612 plasmid Substances 0.000 claims description 16
- 241000588724 Escherichia coli Species 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 11
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 claims description 11
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 claims description 11
- 102000019394 Serine hydroxymethyltransferases Human genes 0.000 claims description 9
- 229960001327 pyridoxal phosphate Drugs 0.000 claims description 8
- 241000588915 Klebsiella aerogenes Species 0.000 claims description 7
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 239000000287 crude extract Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000010353 genetic engineering Methods 0.000 claims description 2
- 150000002463 imidates Chemical class 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 238000002708 random mutagenesis Methods 0.000 claims description 2
- 238000002741 site-directed mutagenesis Methods 0.000 claims description 2
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 claims 2
- 230000000813 microbial effect Effects 0.000 claims 2
- 238000010367 cloning Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 230000001131 transforming effect Effects 0.000 claims 1
- 102000002667 Glycine hydroxymethyltransferase Human genes 0.000 abstract 2
- 229960004279 formaldehyde Drugs 0.000 abstract 2
- 235000019256 formaldehyde Nutrition 0.000 abstract 2
- 108090000623 proteins and genes Proteins 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 244000005700 microbiome Species 0.000 description 7
- 229920002307 Dextran Polymers 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229940024606 amino acid Drugs 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 239000001963 growth medium Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 4
- 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 4
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 238000000855 fermentation Methods 0.000 description 4
- 230000004151 fermentation Effects 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 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 3
- 241000894006 Bacteria Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 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 3
- 101150097303 glyA gene Proteins 0.000 description 3
- 101150079604 glyA1 gene Proteins 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 3
- 229960003495 thiamine Drugs 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000405383 Salmonella enterica subsp. enterica serovar Typhimurium str. LT2 Species 0.000 description 2
- 101100478714 Streptomyces griseus strR gene Proteins 0.000 description 2
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229940044197 ammonium sulfate Drugs 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 239000006143 cell culture medium Substances 0.000 description 2
- 238000007385 chemical modification Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 229960002442 glucosamine Drugs 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- -1 serine Chemical class 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
- 235000019157 thiamine Nutrition 0.000 description 2
- 239000011721 thiamine Substances 0.000 description 2
- 239000012137 tryptone Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- MSTNYGQPCMXVAQ-KIYNQFGBSA-N 5,6,7,8-tetrahydrofolic acid Chemical compound N1C=2C(=O)NC(N)=NC=2NCC1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 MSTNYGQPCMXVAQ-KIYNQFGBSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 1
- 229930195711 D-Serine Natural products 0.000 description 1
- 101100002076 Drosophila melanogaster ara gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 102100023162 L-serine dehydratase/L-threonine deaminase Human genes 0.000 description 1
- 241000872931 Myoporum sandwicense Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000364057 Peoria Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101150078140 SHMT gene Proteins 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 102100035717 Serine racemase Human genes 0.000 description 1
- 108010006152 Serine racemase Proteins 0.000 description 1
- 101100046504 Symbiobacterium thermophilum (strain T / IAM 14863) tnaA2 gene Proteins 0.000 description 1
- 229930003451 Vitamin B1 Natural products 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 229960000723 ampicillin Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 239000011942 biocatalyst Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 230000009483 enzymatic pathway Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000012215 gene cloning Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012913 medium supplement Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 235000006109 methionine Nutrition 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 101150026150 mt gene Proteins 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 101150023849 pheA gene Proteins 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009145 protein modification Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 108020000318 saccharopine dehydrogenase Proteins 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003354 serine derivatives Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 101150006320 trpR gene Proteins 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 239000011691 vitamin B1 Substances 0.000 description 1
- 235000010374 vitamin B1 Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
- C12N9/1003—Transferases (2.) transferring one-carbon groups (2.1)
- C12N9/1014—Hydroxymethyl-, formyl-transferases (2.1.2)
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44296282A | 1982-11-19 | 1982-11-19 | |
| US442,962 | 1982-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1217158A true CA1217158A (en) | 1987-01-27 |
Family
ID=23758887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000441483A Expired CA1217158A (en) | 1982-11-19 | 1983-11-18 | Enzymatic synthesis of l-serine |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS59109187A (de) |
| AU (1) | AU2149383A (de) |
| BE (1) | BE898261A (de) |
| BR (1) | BR8306301A (de) |
| CA (1) | CA1217158A (de) |
| CH (1) | CH657373A5 (de) |
| DE (1) | DE3341763A1 (de) |
| DK (1) | DK529583A (de) |
| ES (1) | ES527388A0 (de) |
| FI (1) | FI834231A (de) |
| FR (1) | FR2536415B1 (de) |
| GB (1) | GB2130216B (de) |
| GR (1) | GR79037B (de) |
| IL (1) | IL70271A0 (de) |
| IT (1) | IT8368213A0 (de) |
| LU (1) | LU85096A1 (de) |
| NL (1) | NL8303978A (de) |
| PL (1) | PL244608A1 (de) |
| SE (1) | SE8306351L (de) |
| ZA (1) | ZA838642B (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104946695A (zh) * | 2015-06-03 | 2015-09-30 | 武汉轻工大学 | 一种l-丝氨酸的制备方法 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60172293A (ja) * | 1984-02-17 | 1985-09-05 | Mitsui Toatsu Chem Inc | Ｌ−セリンの製造法 |
| US4782021A (en) * | 1984-02-17 | 1988-11-01 | Mitsui Toatsu Chemicals, Inc. | Method of producing L-serine |
| EP0165044A3 (de) * | 1984-06-11 | 1987-09-30 | Genex Corporation | Verfahren zum Reagieren einer ein Aldehyd enthaltenden Verbindung mit einer nukleofielen Verbindung |
| JPS6181775A (ja) * | 1984-08-30 | 1986-04-25 | Rikagaku Kenkyusho | 酵素の製造方法 |
| EP0185824A1 (de) * | 1984-12-28 | 1986-07-02 | Genex Corporation | Stabilisierung von Tetrahydrofolinsäure und Serin-Hydroxymethyltransferase in Reaktionsmischungen für die enzymatische Synthese von L-Serin |
| WO1986005515A1 (en) * | 1985-03-18 | 1986-09-25 | Genex Corporation | In vitro synthesis of l-tryptophan |
| US4873359A (en) * | 1985-10-21 | 1989-10-10 | W. R. Grace & Co. - Conn. | Process for preparing as partyl-phenylalanine dipeptides |
| US4810817A (en) * | 1985-10-21 | 1989-03-07 | W. R. Grace & Co. | Aspartyl-beta substituted phenylalanine dipeptides |
| US5102792A (en) * | 1987-08-13 | 1992-04-07 | W. R. Grace & Co.-Conn. | Selective production of L-serine derivative isomers |
| NZ238342A (en) * | 1990-06-04 | 1993-10-26 | Univ Notre Dame Du Lac | Preparation of beta-hydroxy-alphaamino acids useful as intermediates in the preparation of beta-lactam antibiotics |
| US5266468A (en) * | 1990-06-04 | 1993-11-30 | University Of Notre Dame Du Lac | Process for preparing β-hydroxy-α amino acids |
| IL109729A0 (en) * | 1993-05-25 | 1994-08-26 | Lilly Co Eli | Process for preparing serine hydroxymethyl-transferase |
| DE10106461A1 (de) | 2001-02-13 | 2002-08-14 | Degussa | Verfahren zur fermentativen Herstellung von D-Pantothensäure und/oder deren Salzen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS582677B2 (ja) * | 1976-02-12 | 1983-01-18 | 田辺製薬株式会社 | Ｌ−セリンの製法 |
| GB2084155B (en) * | 1980-09-17 | 1984-01-11 | Grace W R & Co | Process for production of l-amino acids using immobilized microorganisms |
-
1983
- 1983-11-16 LU LU85096A patent/LU85096A1/fr unknown
- 1983-11-16 GR GR72996A patent/GR79037B/el unknown
- 1983-11-16 JP JP58214222A patent/JPS59109187A/ja active Pending
- 1983-11-17 SE SE8306351A patent/SE8306351L/ not_active Application Discontinuation
- 1983-11-17 BR BR8306301A patent/BR8306301A/pt unknown
- 1983-11-17 PL PL24460883A patent/PL244608A1/xx unknown
- 1983-11-18 NL NL8303978A patent/NL8303978A/nl not_active Application Discontinuation
- 1983-11-18 AU AU21493/83A patent/AU2149383A/en not_active Abandoned
- 1983-11-18 ES ES527388A patent/ES527388A0/es active Granted
- 1983-11-18 ZA ZA838642A patent/ZA838642B/xx unknown
- 1983-11-18 CH CH6225/83A patent/CH657373A5/de not_active IP Right Cessation
- 1983-11-18 FI FI834231A patent/FI834231A/fi not_active Application Discontinuation
- 1983-11-18 BE BE0/211898A patent/BE898261A/fr not_active IP Right Cessation
- 1983-11-18 IT IT8368213A patent/IT8368213A0/it unknown
- 1983-11-18 IL IL70271A patent/IL70271A0/xx unknown
- 1983-11-18 GB GB08330859A patent/GB2130216B/en not_active Expired
- 1983-11-18 FR FR8318369A patent/FR2536415B1/fr not_active Expired
- 1983-11-18 CA CA000441483A patent/CA1217158A/en not_active Expired
- 1983-11-18 DK DK529583A patent/DK529583A/da not_active Application Discontinuation
- 1983-11-18 DE DE19833341763 patent/DE3341763A1/de not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104946695A (zh) * | 2015-06-03 | 2015-09-30 | 武汉轻工大学 | 一种l-丝氨酸的制备方法 |
| CN104946695B (zh) * | 2015-06-03 | 2018-07-24 | 武汉轻工大学 | 一种l-丝氨酸的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| GR79037B (de) | 1984-10-02 |
| SE8306351L (sv) | 1984-05-20 |
| FI834231A0 (fi) | 1983-11-18 |
| PL244608A1 (en) | 1984-09-24 |
| BE898261A (fr) | 1984-03-16 |
| BR8306301A (pt) | 1984-07-03 |
| FR2536415A1 (fr) | 1984-05-25 |
| IT8368213A0 (it) | 1983-11-18 |
| JPS59109187A (ja) | 1984-06-23 |
| FI834231A (fi) | 1984-05-20 |
| GB2130216B (en) | 1986-04-16 |
| GB8330859D0 (en) | 1983-12-29 |
| IL70271A0 (en) | 1984-02-29 |
| ES8602128A1 (es) | 1985-04-16 |
| FR2536415B1 (fr) | 1987-06-26 |
| DE3341763A1 (de) | 1984-10-04 |
| DK529583D0 (da) | 1983-11-18 |
| SE8306351D0 (sv) | 1983-11-17 |
| GB2130216A (en) | 1984-05-31 |
| LU85096A1 (fr) | 1984-04-02 |
| ES527388A0 (es) | 1985-04-16 |
| DK529583A (da) | 1984-05-20 |
| ZA838642B (en) | 1984-07-25 |
| AU2149383A (en) | 1984-05-24 |
| CH657373A5 (de) | 1986-08-29 |
| NL8303978A (nl) | 1984-06-18 |
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