JPH0523758B2 - - Google Patents
Info
- Publication number
- JPH0523758B2 JPH0523758B2 JP13947883A JP13947883A JPH0523758B2 JP H0523758 B2 JPH0523758 B2 JP H0523758B2 JP 13947883 A JP13947883 A JP 13947883A JP 13947883 A JP13947883 A JP 13947883A JP H0523758 B2 JPH0523758 B2 JP H0523758B2
- Authority
- JP
- Japan
- Prior art keywords
- bacterial cells
- formula
- microorganisms
- group
- methyl
- 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
- 230000001580 bacterial effect Effects 0.000 claims description 15
- 244000005700 microbiome Species 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 241000187654 Nocardia Species 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 241000588986 Alcaligenes Species 0.000 claims description 2
- 241000186359 Mycobacterium Species 0.000 claims description 2
- 241000191940 Staphylococcus Species 0.000 claims description 2
- 241000187747 Streptomyces Species 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- VFVHNRJEYQGRGE-UHFFFAOYSA-N 3-acetylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(C)=O VFVHNRJEYQGRGE-UHFFFAOYSA-N 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- ODXYWRPJDYJIPT-UHFFFAOYSA-N methyl beta-(acetylthio)isobutyrate Chemical compound COC(=O)C(C)CSC(C)=O ODXYWRPJDYJIPT-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 241000589776 Pseudomonas putida Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241000588813 Alcaligenes faecalis Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 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 1
- 241000187481 Mycobacterium phlei Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000187433 Streptomyces clavuligerus Species 0.000 description 1
- 241000187392 Streptomyces griseus Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 229940005347 alcaligenes faecalis Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VLBKKPXFGMZCOX-UHFFFAOYSA-N methyl 2-methyl-2-sulfanylpropanoate Chemical compound COC(=O)C(C)(C)S VLBKKPXFGMZCOX-UHFFFAOYSA-N 0.000 description 1
- GGSFEVYXJOGWLE-UHFFFAOYSA-N methyl 2-methyl-3-oxo-2-(sulfanylmethyl)butanoate Chemical compound COC(=O)C(C)(CS)C(C)=O GGSFEVYXJOGWLE-UHFFFAOYSA-N 0.000 description 1
- ZERPWJMPLLLIIK-UHFFFAOYSA-N methyl 3-benzoylsulfanyl-2-methylpropanoate Chemical compound COC(=O)C(C)CSC(=O)C1=CC=CC=C1 ZERPWJMPLLLIIK-UHFFFAOYSA-N 0.000 description 1
- BECGSBWTFYFALC-UHFFFAOYSA-N methyl 4-acetylsulfanyl-2-methylbutanoate Chemical compound COC(=O)C(C)CCSC(C)=O BECGSBWTFYFALC-UHFFFAOYSA-N 0.000 description 1
- -1 methyl β-mercaptoisobutyrate Chemical compound 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940055036 mycobacterium phlei Drugs 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- YXLNLKOQNYONLE-UHFFFAOYSA-N o-methyl 2-methyl-4-oxopentanethioate Chemical compound COC(=S)C(C)CC(C)=O YXLNLKOQNYONLE-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011782 vitamin Substances 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
- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13947883A JPS6030692A (ja) | 1983-08-01 | 1983-08-01 | 光学活性カルボン酸の製造法 |
| EP84304238A EP0130752B1 (de) | 1983-07-04 | 1984-06-22 | Verfahren zur Herstellung von optisch aktiven Carbonsäuren und von Antipodenestern |
| US06/627,093 US4629701A (en) | 1983-07-04 | 1984-07-02 | Process for preparing optically active carboxylic acids and antipode esters thereof |
| DE19843424440 DE3424440A1 (de) | 1983-07-04 | 1984-07-03 | Verfahren zur herstellung optisch aktiver carbonsaeuren und deren ester in form der optischen antipoden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13947883A JPS6030692A (ja) | 1983-08-01 | 1983-08-01 | 光学活性カルボン酸の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6030692A JPS6030692A (ja) | 1985-02-16 |
| JPH0523758B2 true JPH0523758B2 (de) | 1993-04-05 |
Family
ID=15246182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13947883A Granted JPS6030692A (ja) | 1983-07-04 | 1983-08-01 | 光学活性カルボン酸の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6030692A (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63245694A (ja) * | 1986-11-13 | 1988-10-12 | Showa Shell Sekiyu Kk | 光学活性含硫カルボン酸およびその対掌体エステルの製法 |
-
1983
- 1983-08-01 JP JP13947883A patent/JPS6030692A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6030692A (ja) | 1985-02-16 |
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