JPS6225990A - Ｄ−α−アミノ酸類の製造方法 - Google Patents
Ｄ−α−アミノ酸類の製造方法Info
- Publication number
- JPS6225990A JPS6225990A JP17070886A JP17070886A JPS6225990A JP S6225990 A JPS6225990 A JP S6225990A JP 17070886 A JP17070886 A JP 17070886A JP 17070886 A JP17070886 A JP 17070886A JP S6225990 A JPS6225990 A JP S6225990A
- Authority
- JP
- Japan
- Prior art keywords
- carbamoyl
- group
- manufacturing
- medium
- amino acids
- 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.)
- Granted
Links
- 150000007650 D alpha amino acids Chemical class 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 23
- 108090000790 Enzymes Proteins 0.000 claims abstract description 15
- 102000004190 Enzymes Human genes 0.000 claims abstract description 15
- 241000193830 Bacillus <bacterium> Species 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 9
- 241000192023 Sarcina Species 0.000 claims abstract description 7
- 241000589565 Flavobacterium Species 0.000 claims abstract description 6
- 241000607720 Serratia Species 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical class 0.000 claims abstract description 6
- 125000000547 substituted alkyl group Chemical class 0.000 claims abstract description 6
- 241000186146 Brevibacterium Species 0.000 claims abstract description 5
- 241000607534 Aeromonas Species 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000001544 thienyl group Chemical class 0.000 claims abstract 3
- 230000001580 bacterial effect Effects 0.000 claims description 38
- 239000002609 medium Substances 0.000 claims description 35
- 244000005700 microbiome Species 0.000 claims description 32
- 239000000758 substrate Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 23
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 18
- 150000001469 hydantoins Chemical class 0.000 claims description 13
- 230000001939 inductive effect Effects 0.000 claims description 12
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 11
- 150000003230 pyrimidines Chemical class 0.000 claims description 11
- 229910021645 metal ion Inorganic materials 0.000 claims description 10
- 229940000635 beta-alanine Drugs 0.000 claims description 9
- 229940091173 hydantoin Drugs 0.000 claims description 9
- -1 iron ion Chemical class 0.000 claims description 8
- 239000012736 aqueous medium Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 238000012258 culturing Methods 0.000 claims description 6
- 241000187844 Actinoplanes Species 0.000 claims description 5
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 5
- QCHPKSFMDHPSNR-UHFFFAOYSA-N 3-aminoisobutyric acid Chemical compound NCC(C)C(O)=O QCHPKSFMDHPSNR-UHFFFAOYSA-N 0.000 claims description 4
- 241000186359 Mycobacterium Species 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 230000006698 induction Effects 0.000 claims description 4
- 241000589158 Agrobacterium Species 0.000 claims description 3
- 241000186216 Corynebacterium Species 0.000 claims description 3
- 241000589516 Pseudomonas Species 0.000 claims description 3
- 241000187747 Streptomyces Species 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 2
- PHENTZNALBMCQD-UHFFFAOYSA-N 3-ureidoisobutyric acid Chemical compound OC(=O)C(C)CNC(N)=O PHENTZNALBMCQD-UHFFFAOYSA-N 0.000 claims description 2
- 241000186063 Arthrobacter Species 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 241001467578 Microbacterium Species 0.000 claims description 2
- 241000192041 Micrococcus Species 0.000 claims description 2
- JSJWCHRYRHKBBW-UHFFFAOYSA-N N-carbamoyl-beta-alanine Chemical compound NC(=O)NCCC(O)=O JSJWCHRYRHKBBW-UHFFFAOYSA-N 0.000 claims description 2
- 241000187654 Nocardia Species 0.000 claims description 2
- 241000588769 Proteus <enterobacteria> Species 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 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 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 241000894006 Bacteria Species 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 41
- 239000000243 solution Substances 0.000 description 41
- 210000004027 cell Anatomy 0.000 description 40
- 102100036238 Dihydropyrimidinase Human genes 0.000 description 26
- 108091022884 dihydropyrimidinase Proteins 0.000 description 26
- 230000000694 effects Effects 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 235000013372 meat Nutrition 0.000 description 9
- 230000000813 microbial effect Effects 0.000 description 9
- SBKRXUMXMKBCLD-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)imidazolidine-2,4-dione Chemical compound CSCCC1NC(=O)NC1=O SBKRXUMXMKBCLD-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
- 239000001888 Peptone Substances 0.000 description 8
- 108010080698 Peptones Proteins 0.000 description 8
- 235000019319 peptone Nutrition 0.000 description 8
- UMTNMIARZPDSDI-UHFFFAOYSA-N 5-(4-hydroxyphenyl)imidazolidine-2,4-dione Chemical compound C1=CC(O)=CC=C1C1C(=O)NC(=O)N1 UMTNMIARZPDSDI-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
- 229940041514 candida albicans extract Drugs 0.000 description 6
- 239000001963 growth medium Substances 0.000 description 6
- 239000012138 yeast extract Substances 0.000 description 6
- 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 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- 239000013076 target substance Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-N 0.000 description 4
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 4
- 239000004471 Glycine Substances 0.000 description 4
- GIOUOHDKHHZWIQ-SSDOTTSWSA-N N-carbamoyl-D-phenylglycine Chemical compound NC(=O)N[C@@H](C(O)=O)C1=CC=CC=C1 GIOUOHDKHHZWIQ-SSDOTTSWSA-N 0.000 description 4
- 210000004748 cultured cell Anatomy 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- LSHNGTZXQYSYJQ-UHFFFAOYSA-N 2-(n-carbamoyl-4-hydroxyanilino)acetic acid Chemical compound OC(=O)CN(C(=O)N)C1=CC=C(O)C=C1 LSHNGTZXQYSYJQ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000958221 Streptomyces flaveolus Species 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GIOUOHDKHHZWIQ-UHFFFAOYSA-N 2-(carbamoylamino)-2-phenylacetic acid Chemical compound NC(=O)NC(C(O)=O)C1=CC=CC=C1 GIOUOHDKHHZWIQ-UHFFFAOYSA-N 0.000 description 2
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 2
- VMAQYKGITHDWKL-UHFFFAOYSA-N 5-methylimidazolidine-2,4-dione Chemical compound CC1NC(=O)NC1=O VMAQYKGITHDWKL-UHFFFAOYSA-N 0.000 description 2
- FZRCKLPSHGTOAU-UHFFFAOYSA-N 6-amino-1,4-dimethylcyclohexa-2,4-diene-1-carbaldehyde Chemical compound CC1=CC(N)C(C)(C=O)C=C1 FZRCKLPSHGTOAU-UHFFFAOYSA-N 0.000 description 2
- 241000186361 Actinobacteria <class> Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 241000588914 Enterobacter Species 0.000 description 2
- 241000588697 Enterobacter cloacae Species 0.000 description 2
- 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 2
- 241001509401 Gordonia rubripertincta Species 0.000 description 2
- DEWDMTSMCKXBNP-SCSAIBSYSA-N N-carbamoyl-D-methionine Chemical compound CSCC[C@H](C(O)=O)NC(N)=O DEWDMTSMCKXBNP-SCSAIBSYSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 2
- 150000001371 alpha-amino acids Chemical class 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- IPWQOZCSQLTKOI-MRVPVSSYSA-N (2r)-2-(carbamoylamino)-3-phenylpropanoic acid Chemical compound NC(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 IPWQOZCSQLTKOI-MRVPVSSYSA-N 0.000 description 1
- VJUNTPRQTFDQMF-UHFFFAOYSA-N 1-benzylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)CN1CC1=CC=CC=C1 VJUNTPRQTFDQMF-UHFFFAOYSA-N 0.000 description 1
- MYXWHYDWUWIFRA-UHFFFAOYSA-N 2-(2,4-dioxoimidazolidin-1-yl)acetic acid Chemical compound OC(=O)CN1CC(=O)NC1=O MYXWHYDWUWIFRA-UHFFFAOYSA-N 0.000 description 1
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBAKTGXDIBVZOO-UHFFFAOYSA-N 5,6-dihydrothymine Chemical compound CC1CNC(=O)NC1=O NBAKTGXDIBVZOO-UHFFFAOYSA-N 0.000 description 1
- RYOMFXACAPZPIU-UHFFFAOYSA-N 5-(1-hydroxyethyl)imidazolidine-2,4-dione Chemical compound CC(O)C1NC(=O)NC1=O RYOMFXACAPZPIU-UHFFFAOYSA-N 0.000 description 1
- XLBVUMJAEZCKPE-UHFFFAOYSA-N 5-(2,5-dihydroxyphenyl)imidazolidine-2,4-dione Chemical compound OC1=CC=C(O)C(C2C(NC(=O)N2)=O)=C1 XLBVUMJAEZCKPE-UHFFFAOYSA-N 0.000 description 1
- WLRZLHCGXUHRIG-UHFFFAOYSA-N 5-(2-methylpropyl)imidazolidine-2,4-dione Chemical compound CC(C)CC1NC(=O)NC1=O WLRZLHCGXUHRIG-UHFFFAOYSA-N 0.000 description 1
- SSCQGFVQZYZZSY-UHFFFAOYSA-N 5-(3-aminopropyl)imidazolidine-2,4-dione Chemical compound NCCCC1NC(=O)NC1=O SSCQGFVQZYZZSY-UHFFFAOYSA-N 0.000 description 1
- LWIDUNBRKFUILQ-UHFFFAOYSA-N 5-(3-hydroxyphenyl)imidazolidine-2,4-dione Chemical compound OC1=CC=CC(C2C(NC(=O)N2)=O)=C1 LWIDUNBRKFUILQ-UHFFFAOYSA-N 0.000 description 1
- VQEWBNPYMIPJQY-UHFFFAOYSA-N 5-(4-aminobutyl)imidazolidine-2,4-dione Chemical compound NCCCCC1NC(=O)NC1=O VQEWBNPYMIPJQY-UHFFFAOYSA-N 0.000 description 1
- CBRIRBXLTFAPOM-UHFFFAOYSA-N 5-(hydroxymethyl)imidazolidine-2,4-dione Chemical compound OCC1NC(=O)NC1=O CBRIRBXLTFAPOM-UHFFFAOYSA-N 0.000 description 1
- BBSQTQNQEAVBFC-UHFFFAOYSA-N 5-(methoxymethyl)imidazolidine-2,4-dione Chemical compound COCC1NC(=O)NC1=O BBSQTQNQEAVBFC-UHFFFAOYSA-N 0.000 description 1
- ZUYPRBNQYTZYIK-UHFFFAOYSA-N 5-butan-2-ylimidazolidine-2,4-dione Chemical compound CCC(C)C1NC(=O)NC1=O ZUYPRBNQYTZYIK-UHFFFAOYSA-N 0.000 description 1
- JZBMVRBRZUZZCT-UHFFFAOYSA-N 5-butylimidazolidine-2,4-dione Chemical compound CCCCC1NC(=O)NC1=O JZBMVRBRZUZZCT-UHFFFAOYSA-N 0.000 description 1
- RSBRXBZGVHQUJK-UHFFFAOYSA-N 5-ethylimidazolidine-2,4-dione Chemical compound CCC1NC(=O)NC1=O RSBRXBZGVHQUJK-UHFFFAOYSA-N 0.000 description 1
- NXQJDVBMMRCKQG-UHFFFAOYSA-N 5-phenylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=CC=CC=C1 NXQJDVBMMRCKQG-UHFFFAOYSA-N 0.000 description 1
- PBNUQCWZHRMSMS-UHFFFAOYSA-N 5-propan-2-ylimidazolidine-2,4-dione Chemical compound CC(C)C1NC(=O)NC1=O PBNUQCWZHRMSMS-UHFFFAOYSA-N 0.000 description 1
- BIFASJFFCIDWDC-UHFFFAOYSA-N 5-propylimidazolidine-2,4-dione Chemical compound CCCC1NC(=O)NC1=O BIFASJFFCIDWDC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000590020 Achromobacter Species 0.000 description 1
- 241000186046 Actinomyces Species 0.000 description 1
- 241000607528 Aeromonas hydrophila Species 0.000 description 1
- 241000589156 Agrobacterium rhizogenes Species 0.000 description 1
- 241000588986 Alcaligenes Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000193408 Bacillus badius Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000186145 Corynebacterium ammoniagenes Species 0.000 description 1
- 241001134763 Corynebacterium flavescens Species 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
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- ROHFNLRQFUQHCH-RXMQYKEDSA-N D-leucine Chemical compound CC(C)C[C@@H](N)C(O)=O ROHFNLRQFUQHCH-RXMQYKEDSA-N 0.000 description 1
- 229930182819 D-leucine Natural products 0.000 description 1
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 description 1
- 229930182832 D-phenylalanine Natural products 0.000 description 1
- 241001635321 Desemzia incerta Species 0.000 description 1
- 244000182625 Dictamnus albus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001058146 Erium Species 0.000 description 1
- 241000588698 Erwinia Species 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- 241000191948 Kocuria rosea Species 0.000 description 1
- 241001468261 Lysinibacillus macroides Species 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- 241000588772 Morganella morganii Species 0.000 description 1
- 241000178961 Paenibacillus alvei Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- 241000203720 Pimelobacter simplex Species 0.000 description 1
- 241000586779 Protaminobacter Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241001148118 Xanthomonas sp. Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012531 culture fluid Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229940104302 cytosine Drugs 0.000 description 1
- IPWQOZCSQLTKOI-QMMMGPOBSA-N d-[(amino)carbonyl]phenylalanine Chemical compound NC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 IPWQOZCSQLTKOI-QMMMGPOBSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- VWFWNXQAMGDPGG-UHFFFAOYSA-N hydantoin-5-propionic acid Chemical compound OC(=O)CCC1NC(=O)NC1=O VWFWNXQAMGDPGG-UHFFFAOYSA-N 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229910001437 manganese ion Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000009629 microbiological culture Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LUSWEUMSEVLFEQ-UWTATZPHSA-N n-carbamoyl-alanine Chemical compound OC(=O)[C@@H](C)NC(N)=O LUSWEUMSEVLFEQ-UWTATZPHSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17070886A JPS6225990A (ja) | 1986-07-19 | 1986-07-19 | Ｄ−α−アミノ酸類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17070886A JPS6225990A (ja) | 1986-07-19 | 1986-07-19 | Ｄ−α−アミノ酸類の製造方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1262279A Division JPS55104890A (en) | 1979-02-06 | 1979-02-06 | Production of d-alpha-aminoacids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6225990A true JPS6225990A (ja) | 1987-02-03 |
| JPH0148758B2 JPH0148758B2 (enrdf_load_stackoverflow) | 1989-10-20 |
Family
ID=15909925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17070886A Granted JPS6225990A (ja) | 1986-07-19 | 1986-07-19 | Ｄ−α−アミノ酸類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6225990A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5863785A (en) * | 1992-10-05 | 1999-01-26 | Kanegafuchi Chemical Industry Co., Ltd. | Decarbamylase isolated from comamonas or blastobacter |
| EP1213354A3 (en) * | 2000-12-07 | 2003-02-05 | Sumitomo Chemical Company, Limited | Process for producing optically active 4-halo-3-hydroxybutanoate |
| JP2014533497A (ja) * | 2011-11-16 | 2014-12-15 | エボニック インダストリーズ アクチエンゲゼルシャフトＥｖｏｎｉｋ Ｉｎｄｕｓｔｒｉｅｓ ＡＧ | ヒダントイナーゼの突然変異体 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5096911B2 (ja) | 2005-01-31 | 2012-12-12 | 株式会社カネカ | ５−置換ヒダントインラセマーゼ、これをコードするｄｎａ、組換えｄｎａ、形質転換された細胞、および、光学活性ｎ−カルバミルアミノ酸または光学活性アミノ酸の製造方法 |
| AU2015360291A1 (en) | 2014-12-11 | 2017-07-13 | President And Fellows Of Harvard College | Inhibitors of cellular necrosis and related methods |
-
1986
- 1986-07-19 JP JP17070886A patent/JPS6225990A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5863785A (en) * | 1992-10-05 | 1999-01-26 | Kanegafuchi Chemical Industry Co., Ltd. | Decarbamylase isolated from comamonas or blastobacter |
| US5902736A (en) * | 1992-10-05 | 1999-05-11 | Kanegafuchi Chemical Industry Co., Ltd. | Process for the production of D-α-amino acids by hydrolysis of the corresponding N-carbamyl derivative |
| EP1213354A3 (en) * | 2000-12-07 | 2003-02-05 | Sumitomo Chemical Company, Limited | Process for producing optically active 4-halo-3-hydroxybutanoate |
| US6884607B2 (en) | 2000-12-07 | 2005-04-26 | Sumitomo Chemical Company, Limited | Process for producing optically active 4-halo-3-hydroxybutanoate |
| JP2014533497A (ja) * | 2011-11-16 | 2014-12-15 | エボニック インダストリーズ アクチエンゲゼルシャフトＥｖｏｎｉｋ Ｉｎｄｕｓｔｒｉｅｓ ＡＧ | ヒダントイナーゼの突然変異体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0148758B2 (enrdf_load_stackoverflow) | 1989-10-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL192118C (nl) | Enzymatische microbiologische werkwijze voor de bereiding van optisch aktieve aminozuren uit hydanthoinen en/of racemische carbamoylverbindin- gen. | |
| US3945888A (en) | Method for the production of cephalosporins | |
| CA1196591A (en) | Process for producing ribavirin | |
| JPS6230758B2 (enrdf_load_stackoverflow) | ||
| US4237227A (en) | Process for preparing D-N-carbamoyl-α-amino acids | |
| JPH04228065A (ja) | クロトノベタインからｌ−（−）−カルニチンの製法 | |
| JPS6225990A (ja) | Ｄ−α−アミノ酸類の製造方法 | |
| JPS6129953B2 (enrdf_load_stackoverflow) | ||
| JPS60180596A (ja) | Ｌ‐α‐アミノ酸の製法 | |
| US5215897A (en) | Process for producing L-amino acids | |
| Sakai et al. | Formation of β-cyanoalanine by cyanide-resistant strain Enterobacter sp. 10-1 | |
| JPH01320991A (ja) | Ｄ−ホモフエニルアラニン類の製造方法 | |
| US5906927A (en) | Process for producing L-2-aminoadipic acid | |
| JPH02291291A (ja) | ジデオキシイノシンの製造方法 | |
| US4349627A (en) | Process for producing L-tryptophan or derivatives thereof using a microorganism | |
| US4360594A (en) | Process for producing L-tryptophan or derivatives thereof using microorganisms | |
| CH643299A5 (fr) | Procede de preparation de d-alpha-amino-acides. | |
| JP2674076B2 (ja) | Ｄ−α−アミノ酸の製造方法 | |
| JPS6125359B2 (enrdf_load_stackoverflow) | ||
| JPH0449997B2 (enrdf_load_stackoverflow) | ||
| JP2899071B2 (ja) | Ｌ―α―アラニンの製造法 | |
| JPH0542427B2 (enrdf_load_stackoverflow) | ||
| JPH0339676B2 (enrdf_load_stackoverflow) | ||
| JPS5928486A (ja) | Ｓ−カルボキシメチル−ｌ−システインの製造法 | |
| JPH01265896A (ja) | Ｄ−α−アミノ酸の製造法 |