JPH02207799A - 光学活性３―フェニルグリシッド酸エステル類化合物の単離方法 - Google Patents
光学活性３―フェニルグリシッド酸エステル類化合物の単離方法Info
- Publication number
- JPH02207799A JPH02207799A JP2641789A JP2641789A JPH02207799A JP H02207799 A JPH02207799 A JP H02207799A JP 2641789 A JP2641789 A JP 2641789A JP 2641789 A JP2641789 A JP 2641789A JP H02207799 A JPH02207799 A JP H02207799A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- organic solvent
- acid ester
- water
- phase
- 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
- 238000000034 method Methods 0.000 title claims description 23
- 239000003960 organic solvent Substances 0.000 claims abstract description 28
- -1 sulfurous acid ion Chemical class 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 21
- 238000006911 enzymatic reaction Methods 0.000 claims abstract description 20
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229940079826 hydrogen sulfite Drugs 0.000 claims abstract description 9
- 239000012046 mixed solvent Substances 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 108090000604 Hydrolases Proteins 0.000 claims abstract description 7
- 102000004157 Hydrolases Human genes 0.000 claims abstract description 7
- 108090001060 Lipase Proteins 0.000 claims abstract description 6
- 102000004882 Lipase Human genes 0.000 claims abstract description 6
- 239000004367 Lipase Substances 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 6
- 235000019421 lipase Nutrition 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 239000012071 phase Substances 0.000 claims description 27
- 108090000790 Enzymes Proteins 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 claims 1
- 108090000371 Esterases Proteins 0.000 abstract description 3
- 239000012295 chemical reaction liquid Substances 0.000 abstract 2
- 239000000047 product Substances 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000001580 bacterial effect Effects 0.000 description 9
- 239000013078 crystal Substances 0.000 description 7
- 241000235527 Rhizopus Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- CVZUMGUZDAWOGA-UHFFFAOYSA-N methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate Chemical compound COC(=O)C1OC1C1=CC=C(OC)C=C1 CVZUMGUZDAWOGA-UHFFFAOYSA-N 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FEDJGPQLLNQAIY-UHFFFAOYSA-N 2-[(6-oxo-1h-pyridazin-3-yl)oxy]acetic acid Chemical compound OC(=O)COC=1C=CC(=O)NN=1 FEDJGPQLLNQAIY-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 241000235389 Absidia Species 0.000 description 1
- 241000590020 Achromobacter Species 0.000 description 1
- 241000186361 Actinobacteria <class> Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000146387 Chromobacterium viscosum Species 0.000 description 1
- 241000222175 Diutina rugosa Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000498617 Mucor javanicus Species 0.000 description 1
- 241000187654 Nocardia Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000589538 Pseudomonas fragi Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 108010055297 Sterol Esterase Proteins 0.000 description 1
- 102000000019 Sterol Esterase Human genes 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 229960005316 diltiazem hydrochloride Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- CVZUMGUZDAWOGA-VHSXEESVSA-N methyl (2r,3s)-3-(4-methoxyphenyl)oxirane-2-carboxylate Chemical compound COC(=O)[C@@H]1O[C@H]1C1=CC=C(OC)C=C1 CVZUMGUZDAWOGA-VHSXEESVSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2641789A JPH02207799A (ja) | 1989-02-03 | 1989-02-03 | 光学活性３―フェニルグリシッド酸エステル類化合物の単離方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2641789A JPH02207799A (ja) | 1989-02-03 | 1989-02-03 | 光学活性３―フェニルグリシッド酸エステル類化合物の単離方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02207799A true JPH02207799A (ja) | 1990-08-17 |
| JPH0560919B2 JPH0560919B2 (cs) | 1993-09-03 |
Family
ID=12192962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2641789A Granted JPH02207799A (ja) | 1989-02-03 | 1989-02-03 | 光学活性３―フェニルグリシッド酸エステル類化合物の単離方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02207799A (cs) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02109995A (ja) * | 1988-05-20 | 1990-04-23 | Stamicarbon Bv | 立体異性体的に純粋なフエニルグリシド酸エステルの製造方法および（２ｓ，３ｓ）‐２‐（４′‐メトキシフエニル）‐３‐アセトキシ‐５‐〔２‐（ジメチルアミノ）エチル〕‐２，３‐ジヒドロ‐１，５‐ベンゾチアゼピン‐４（５ｈ）‐オンの製造方法 |
-
1989
- 1989-02-03 JP JP2641789A patent/JPH02207799A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02109995A (ja) * | 1988-05-20 | 1990-04-23 | Stamicarbon Bv | 立体異性体的に純粋なフエニルグリシド酸エステルの製造方法および（２ｓ，３ｓ）‐２‐（４′‐メトキシフエニル）‐３‐アセトキシ‐５‐〔２‐（ジメチルアミノ）エチル〕‐２，３‐ジヒドロ‐１，５‐ベンゾチアゼピン‐４（５ｈ）‐オンの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0560919B2 (cs) | 1993-09-03 |
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Legal Events
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| R250 | Receipt of annual fees |
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| LAPS | Cancellation because of no payment of annual fees |