JPS6230758B2 - - Google Patents
Info
- Publication number
- JPS6230758B2 JPS6230758B2 JP54012622A JP1262279A JPS6230758B2 JP S6230758 B2 JPS6230758 B2 JP S6230758B2 JP 54012622 A JP54012622 A JP 54012622A JP 1262279 A JP1262279 A JP 1262279A JP S6230758 B2 JPS6230758 B2 JP S6230758B2
- Authority
- JP
- Japan
- Prior art keywords
- genus
- hydantoin
- carbamoyl
- substituted
- medium
- 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
- 244000005700 microbiome Species 0.000 claims description 30
- 239000000758 substrate Substances 0.000 claims description 26
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 24
- 150000001469 hydantoins Chemical class 0.000 claims description 18
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 229940091173 hydantoin Drugs 0.000 claims description 13
- 229940000635 beta-alanine Drugs 0.000 claims description 12
- 229910021645 metal ion Inorganic materials 0.000 claims description 12
- 150000003230 pyrimidines Chemical class 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- -1 iron ions Chemical class 0.000 claims description 8
- 241000187844 Actinoplanes Species 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000012258 culturing Methods 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
- 241000186216 Corynebacterium Species 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
- 241000187654 Nocardia Species 0.000 claims description 4
- 241000589516 Pseudomonas Species 0.000 claims description 4
- 241000187747 Streptomyces Species 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000006698 induction Effects 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 3
- 241000588769 Proteus <enterobacteria> Species 0.000 claims description 3
- 241000192023 Sarcina Species 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 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
- 241000590020 Achromobacter Species 0.000 claims description 2
- 241000186046 Actinomyces Species 0.000 claims description 2
- 241000607534 Aeromonas Species 0.000 claims description 2
- 241000589158 Agrobacterium Species 0.000 claims description 2
- 241000588986 Alcaligenes Species 0.000 claims description 2
- 241000186063 Arthrobacter Species 0.000 claims description 2
- 241000228212 Aspergillus Species 0.000 claims description 2
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 2
- 241000186146 Brevibacterium Species 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 241000588914 Enterobacter Species 0.000 claims description 2
- 241000588698 Erwinia Species 0.000 claims description 2
- 241000588722 Escherichia Species 0.000 claims description 2
- 241000588748 Klebsiella Species 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
- 241000228143 Penicillium Species 0.000 claims description 2
- 241000235648 Pichia Species 0.000 claims description 2
- 241000586779 Protaminobacter Species 0.000 claims description 2
- 241000223252 Rhodotorula Species 0.000 claims description 2
- 241000607720 Serratia Species 0.000 claims description 2
- 241000589634 Xanthomonas 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
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 claims 1
- 241000589159 Agrobacterium sp. Species 0.000 claims 1
- 241000186073 Arthrobacter sp. Species 0.000 claims 1
- 241000194110 Bacillus sp. (in: Bacteria) Species 0.000 claims 1
- 241000186312 Brevibacterium sp. Species 0.000 claims 1
- 241000186249 Corynebacterium sp. Species 0.000 claims 1
- 241000500375 Microbacterium sp. Species 0.000 claims 1
- 241001236817 Paecilomyces <Clavicipitaceae> Species 0.000 claims 1
- 241001037421 Sarcina sp. Species 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 48
- 239000000243 solution Substances 0.000 description 45
- 239000002609 medium Substances 0.000 description 37
- 102100036238 Dihydropyrimidinase Human genes 0.000 description 31
- 108091022884 dihydropyrimidinase Proteins 0.000 description 31
- 210000004027 cell Anatomy 0.000 description 29
- 230000001580 bacterial effect Effects 0.000 description 23
- 238000000034 method Methods 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 150000007650 D alpha amino acids Chemical class 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- SBKRXUMXMKBCLD-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)imidazolidine-2,4-dione Chemical compound CSCCC1NC(=O)NC1=O SBKRXUMXMKBCLD-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 230000000813 microbial effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000001939 inductive effect Effects 0.000 description 8
- 235000013372 meat Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229920001817 Agar Polymers 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- 241000958221 Streptomyces flaveolus Species 0.000 description 7
- 239000008272 agar Substances 0.000 description 7
- 229940041514 candida albicans extract Drugs 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000006228 supernatant Substances 0.000 description 7
- 239000012138 yeast extract Substances 0.000 description 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 239000001888 Peptone Substances 0.000 description 6
- 108010080698 Peptones Proteins 0.000 description 6
- 235000008206 alpha-amino acids Nutrition 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 235000019319 peptone Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 230000001954 sterilising effect Effects 0.000 description 5
- 238000004659 sterilization and disinfection Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 241000894006 Bacteria Species 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 150000001371 alpha-amino acids Chemical class 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 210000004748 cultured cell Anatomy 0.000 description 4
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 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 3
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 241000193764 Brevibacillus brevis Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000004471 Glycine Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 3
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 2
- WPJLWWOKUOJTOU-UHFFFAOYSA-N 5-(3-chlorophenyl)imidazolidine-2,4-dione Chemical compound ClC1=CC=CC(C2C(NC(=O)N2)=O)=C1 WPJLWWOKUOJTOU-UHFFFAOYSA-N 0.000 description 2
- DBOMTIHROGSFTI-UHFFFAOYSA-N 5-benzylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1CC1=CC=CC=C1 DBOMTIHROGSFTI-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
- 241000589156 Agrobacterium rhizogenes 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
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000012450 pharmaceutical intermediate Substances 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 241000894007 species Species 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
- DQQLZADYSWBCOX-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)acetic acid Chemical compound OC(=O)CC1NC(=O)NC1=O DQQLZADYSWBCOX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XLMSKXASROPJNG-UHFFFAOYSA-N 2-azaniumyl-2-thiophen-2-ylacetate Chemical compound OC(=O)C(N)C1=CC=CS1 XLMSKXASROPJNG-UHFFFAOYSA-N 0.000 description 1
- MMDZBDLRGFUSSP-UHFFFAOYSA-N 3-(2,5-dioxoimidazolidin-4-yl)propanenitrile Chemical compound O=C1NC(CCC#N)C(=O)N1 MMDZBDLRGFUSSP-UHFFFAOYSA-N 0.000 description 1
- DBKOXARNAKRIDK-UHFFFAOYSA-N 4-(2,5-dioxoimidazolidin-4-yl)butanenitrile Chemical compound O=C1NC(CCCC#N)C(=O)N1 DBKOXARNAKRIDK-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
- 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
- WKDQEQZCZLTWFV-UHFFFAOYSA-N 5-(2,4-dihydroxyphenyl)imidazolidine-2,4-dione Chemical compound OC1=CC(O)=CC=C1C1C(=O)NC(=O)N1 WKDQEQZCZLTWFV-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
- FWBPEGIHSRGDLJ-UHFFFAOYSA-N 5-(2,5-dimethoxyphenyl)imidazolidine-2,4-dione Chemical compound COC1=CC=C(OC)C(C2C(NC(=O)N2)=O)=C1 FWBPEGIHSRGDLJ-UHFFFAOYSA-N 0.000 description 1
- ZGUGVTBDORBTHA-UHFFFAOYSA-N 5-(2-chlorophenyl)imidazolidine-2,4-dione Chemical compound ClC1=CC=CC=C1C1C(=O)NC(=O)N1 ZGUGVTBDORBTHA-UHFFFAOYSA-N 0.000 description 1
- VZOVQUZTJMFYIN-UHFFFAOYSA-N 5-(2-fluorophenyl)imidazolidine-2,4-dione Chemical compound FC1=CC=CC=C1C1C(=O)NC(=O)N1 VZOVQUZTJMFYIN-UHFFFAOYSA-N 0.000 description 1
- RHZABNRRZHUTNE-UHFFFAOYSA-N 5-(2-hydroxy-4-methoxyphenyl)imidazolidine-2,4-dione Chemical compound OC1=CC(OC)=CC=C1C1C(=O)NC(=O)N1 RHZABNRRZHUTNE-UHFFFAOYSA-N 0.000 description 1
- NGLDWGIPFRHVFB-UHFFFAOYSA-N 5-(2-hydroxy-5-methoxyphenyl)imidazolidine-2,4-dione Chemical compound COC1=CC=C(O)C(C2C(NC(=O)N2)=O)=C1 NGLDWGIPFRHVFB-UHFFFAOYSA-N 0.000 description 1
- BVERFRYWSPRASF-UHFFFAOYSA-N 5-(2-hydroxyethyl)imidazolidine-2,4-dione Chemical compound OCCC1NC(=O)NC1=O BVERFRYWSPRASF-UHFFFAOYSA-N 0.000 description 1
- GKVUJUZMDDAMHS-UHFFFAOYSA-N 5-(2-hydroxyphenyl)imidazolidine-2,4-dione Chemical compound OC1=CC=CC=C1C1C(=O)NC(=O)N1 GKVUJUZMDDAMHS-UHFFFAOYSA-N 0.000 description 1
- RBRCHMYEBAVDIS-UHFFFAOYSA-N 5-(2-methylphenyl)imidazolidine-2,4-dione Chemical compound CC1=CC=CC=C1C1C(=O)NC(=O)N1 RBRCHMYEBAVDIS-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
- UZHGPHDIPRADRK-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)imidazolidine-2,4-dione Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C(=O)NC(=O)N1 UZHGPHDIPRADRK-UHFFFAOYSA-N 0.000 description 1
- WWSABODBEODTEA-UHFFFAOYSA-N 5-(3,4-dihydroxyphenyl)imidazolidine-2,4-dione Chemical compound C1=C(O)C(O)=CC=C1C1C(=O)NC(=O)N1 WWSABODBEODTEA-UHFFFAOYSA-N 0.000 description 1
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- 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
- C12N9/14—Hydrolases (3)
- C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
- C12N9/86—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in cyclic amides, e.g. penicillinase (3.5.2)
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- 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
- C12N9/14—Hydrolases (3)
- C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
- C12N9/80—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in linear amides (3.5.1)
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
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- 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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1262279A JPS55104890A (en) | 1979-02-06 | 1979-02-06 | Production of d-alpha-aminoacids |
| GB8003219A GB2042531B (en) | 1979-02-06 | 1980-01-31 | Process for preparing d- -amino acids |
| IT47797/80A IT1143925B (it) | 1979-02-06 | 1980-02-04 | Procedimento per preparare d-alfaam minoacidi |
| BE0/199262A BE881547A (fr) | 1979-02-06 | 1980-02-05 | Procede de preparation de d-alpha-amino acides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1262279A JPS55104890A (en) | 1979-02-06 | 1979-02-06 | Production of d-alpha-aminoacids |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17070886A Division JPS6225990A (ja) | 1986-07-19 | 1986-07-19 | Ｄ−α−アミノ酸類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55104890A JPS55104890A (en) | 1980-08-11 |
| JPS6230758B2 true JPS6230758B2 (ru) | 1987-07-03 |
Family
ID=11810467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1262279A Granted JPS55104890A (en) | 1979-02-06 | 1979-02-06 | Production of d-alpha-aminoacids |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS55104890A (ru) |
| BE (1) | BE881547A (ru) |
| GB (1) | GB2042531B (ru) |
| IT (1) | IT1143925B (ru) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3031151A1 (de) | 1980-08-18 | 1982-04-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von d-n-carbamoyl-(alpha)-aminosaeuren und mikroorganismen dafuer |
| DK164923C (da) * | 1984-04-11 | 1993-01-25 | Denki Kagaku Kogyo Kk | Fremgangsmaade til fremstilling af l-alfa-aminosyrer |
| JPS61212292A (ja) * | 1985-03-19 | 1986-09-20 | Mitsui Toatsu Chem Inc | Ｄ−α−アミノ酸の製造方法 |
| DE3535987A1 (de) * | 1985-10-09 | 1987-04-23 | Basf Ag | Verfahren zur herstellung von meophilen mikroorganismen, die eine bei hoeherer temperatur aktive d-hydantoinase enthalten |
| US5283182A (en) * | 1986-09-17 | 1994-02-01 | Beecham Group Plc | Preparation of immobilized hydantoinase stabilized with divalent metal ions |
| DE3702384A1 (de) * | 1987-01-23 | 1988-08-04 | Schering Ag | Verfahren zur herstellung von l-aminosaeuren |
| FR2620731B1 (fr) * | 1987-09-21 | 1990-03-23 | Hoechst France | Nouveau systeme enzymatique, son procede de preparation et son application notamment dans la preparation de la d-parahydroxyphenylglycine |
| JPH01320991A (ja) * | 1988-06-20 | 1989-12-27 | Kanegafuchi Chem Ind Co Ltd | Ｄ−ホモフエニルアラニン類の製造方法 |
| US5824522A (en) * | 1990-12-07 | 1998-10-20 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Recombinant decarbamylases for producing D-α-amino acids |
| ES2042409B1 (es) * | 1992-04-10 | 1994-06-01 | Control & Gestion Instr | Procedimiento para la preparacion de d-aminoacidos o derivados de d-aminoacidos. |
| DE10130169A1 (de) * | 2001-06-22 | 2003-01-09 | Degussa | Aktivierte rec-D-Hydantoinasen |
| EP1500386A1 (en) * | 2003-07-23 | 2005-01-26 | Wella Aktiengesellschaft | Method for time-dependent decrease of ph in a cosmetic composition and a composition for permanent hair shaping with time-dependent decrease of the wave-shaping efficiency |
| EP1867730A1 (en) * | 2005-03-23 | 2007-12-19 | Ajinomoto Co., Inc. | Process for production of optically active hydroxymethyl -substituted phenylalanine |
-
1979
- 1979-02-06 JP JP1262279A patent/JPS55104890A/ja active Granted
-
1980
- 1980-01-31 GB GB8003219A patent/GB2042531B/en not_active Expired
- 1980-02-04 IT IT47797/80A patent/IT1143925B/it active
- 1980-02-05 BE BE0/199262A patent/BE881547A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2042531A (en) | 1980-09-24 |
| GB2042531B (en) | 1983-09-28 |
| IT8047797A0 (it) | 1980-02-04 |
| IT1143925B (it) | 1986-10-29 |
| JPS55104890A (en) | 1980-08-11 |
| BE881547A (fr) | 1980-05-30 |
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