JPH0513631B2 - - Google Patents
Info
- Publication number
- JPH0513631B2 JPH0513631B2 JP9689485A JP9689485A JPH0513631B2 JP H0513631 B2 JPH0513631 B2 JP H0513631B2 JP 9689485 A JP9689485 A JP 9689485A JP 9689485 A JP9689485 A JP 9689485A JP H0513631 B2 JPH0513631 B2 JP H0513631B2
- Authority
- JP
- Japan
- Prior art keywords
- benzylserine
- genus
- optically active
- dihydroxyphenylalanine
- 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 - Lifetime
Links
- IDGQXGPQOGUGIX-VIFPVBQESA-N O-BENZYL-l-SERINE Chemical compound OC(=O)[C@@H](N)COCC1=CC=CC=C1 IDGQXGPQOGUGIX-VIFPVBQESA-N 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 18
- 244000005700 microbiome Species 0.000 claims description 16
- 230000006340 racemization Effects 0.000 claims description 8
- 241000589565 Flavobacterium Species 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 7
- 241000228143 Penicillium Species 0.000 claims description 4
- 241000235648 Pichia Species 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 241000590020 Achromobacter Species 0.000 claims description 3
- 241000588698 Erwinia Species 0.000 claims description 3
- 241000589516 Pseudomonas Species 0.000 claims description 3
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 2
- 241000589291 Acinetobacter 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
- 241000400328 Arachniotus Species 0.000 claims description 2
- 241000186063 Arthrobacter Species 0.000 claims description 2
- 241000228212 Aspergillus Species 0.000 claims description 2
- 241000223651 Aureobasidium Species 0.000 claims description 2
- 241000186146 Brevibacterium Species 0.000 claims description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 2
- 241000186321 Cellulomonas Species 0.000 claims description 2
- 241001123632 Cephaloascus Species 0.000 claims description 2
- 241000221955 Chaetomium Species 0.000 claims description 2
- 241000588923 Citrobacter Species 0.000 claims description 2
- 241000228437 Cochliobolus Species 0.000 claims description 2
- 241000186216 Corynebacterium Species 0.000 claims description 2
- 241000609458 Corynespora Species 0.000 claims description 2
- 241000235035 Debaryomyces Species 0.000 claims description 2
- 241000588914 Enterobacter Species 0.000 claims description 2
- 241000588722 Escherichia Species 0.000 claims description 2
- 241000223218 Fusarium Species 0.000 claims description 2
- 241000159512 Geotrichum Species 0.000 claims description 2
- 241000896533 Gliocladium Species 0.000 claims description 2
- 241000223247 Gloeocercospora Species 0.000 claims description 2
- 241000985936 Gymnoascus Species 0.000 claims description 2
- 241000116139 Hamigera <sponge> Species 0.000 claims description 2
- 241000223198 Humicola Species 0.000 claims description 2
- 241000588748 Klebsiella Species 0.000 claims description 2
- 241001149698 Lipomyces Species 0.000 claims description 2
- 241000124167 Melanospora Species 0.000 claims description 2
- 241000223609 Microascus Species 0.000 claims description 2
- 241000908267 Moniliella Species 0.000 claims description 2
- 241000235395 Mucor Species 0.000 claims description 2
- 241000221960 Neurospora Species 0.000 claims description 2
- 241000193804 Planococcus <bacterium> Species 0.000 claims description 2
- 241000221945 Podospora Species 0.000 claims description 2
- 241000586779 Protaminobacter Species 0.000 claims description 2
- 241000588769 Proteus <enterobacteria> Species 0.000 claims description 2
- 241000235527 Rhizopus Species 0.000 claims description 2
- 241000607142 Salmonella Species 0.000 claims description 2
- 241000221948 Sordaria Species 0.000 claims description 2
- 241000165775 Sporormiella Species 0.000 claims description 2
- 241000533281 Stagonospora Species 0.000 claims description 2
- 241000187747 Streptomyces Species 0.000 claims description 2
- 241000223230 Trichosporon Species 0.000 claims description 2
- 241001480014 Trigonopsis Species 0.000 claims description 2
- 241000221566 Ustilago Species 0.000 claims description 2
- 241000607598 Vibrio Species 0.000 claims description 2
- 229940048278 septra Drugs 0.000 claims description 2
- 241001327444 Coniochaeta Species 0.000 claims 1
- 241000223208 Curvularia Species 0.000 claims 1
- 241000192041 Micrococcus Species 0.000 claims 1
- 241000222665 Sterigmatomyces Species 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 20
- 230000001580 bacterial effect Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- 239000002609 medium Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 229960004441 tyrosine Drugs 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 8
- 108091000100 Tyrosine Phenol-Lyase Proteins 0.000 description 8
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- UTIMIHJZXIJZKZ-ZETCQYMHSA-N (2S)-2-amino-3-(2,4-dihydroxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1O UTIMIHJZXIJZKZ-ZETCQYMHSA-N 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 230000001954 sterilising effect Effects 0.000 description 5
- 238000004659 sterilization and disinfection Methods 0.000 description 5
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910001410 inorganic ion Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- IDGQXGPQOGUGIX-SECBINFHSA-N (2r)-2-amino-3-phenylmethoxypropanoic acid Chemical compound OC(=O)[C@H](N)COCC1=CC=CC=C1 IDGQXGPQOGUGIX-SECBINFHSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria 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
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 2
- 241000588912 Pantoea agglomerans Species 0.000 description 2
- RADKZDMFGJYCBB-UHFFFAOYSA-N Pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 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 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- -1 iron ions Chemical class 0.000 description 2
- 229960004502 levodopa Drugs 0.000 description 2
- 229910001425 magnesium ion Inorganic materials 0.000 description 2
- 239000011785 micronutrient Substances 0.000 description 2
- 235000013369 micronutrients Nutrition 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 229910001414 potassium ion Inorganic materials 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
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 2
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229960001153 serine Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- 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 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- IDGQXGPQOGUGIX-UHFFFAOYSA-N O-Benzyl-DL-serine Chemical compound OC(=O)C(N)COCC1=CC=CC=C1 IDGQXGPQOGUGIX-UHFFFAOYSA-N 0.000 description 1
- 241000316848 Rhodococcus <scale insect> Species 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 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
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012531 culture fluid Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001742 protein purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229960003581 pyridoxal Drugs 0.000 description 1
- 235000008164 pyridoxal Nutrition 0.000 description 1
- 239000011674 pyridoxal Substances 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004172 pyridoxine hydrochloride Drugs 0.000 description 1
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 1
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 1
- 229940089808 pyridoxine hydrochloride 10 mg Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9689485A JPS61257193A (ja) | 1985-05-08 | 1985-05-08 | 光学活性ｏ−ベンジルセリンのラセミ化法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9689485A JPS61257193A (ja) | 1985-05-08 | 1985-05-08 | 光学活性ｏ−ベンジルセリンのラセミ化法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61257193A JPS61257193A (ja) | 1986-11-14 |
| JPH0513631B2 true JPH0513631B2 (ko) | 1993-02-23 |
Family
ID=14177082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9689485A Granted JPS61257193A (ja) | 1985-05-08 | 1985-05-08 | 光学活性ｏ−ベンジルセリンのラセミ化法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61257193A (ko) |
-
1985
- 1985-05-08 JP JP9689485A patent/JPS61257193A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61257193A (ja) | 1986-11-14 |
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