JPH0533994B2 - - Google Patents
Info
- Publication number
- JPH0533994B2 JPH0533994B2 JP10180384A JP10180384A JPH0533994B2 JP H0533994 B2 JPH0533994 B2 JP H0533994B2 JP 10180384 A JP10180384 A JP 10180384A JP 10180384 A JP10180384 A JP 10180384A JP H0533994 B2 JPH0533994 B2 JP H0533994B2
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- formula
- aqueous medium
- optically active
- group
- 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 - Fee Related
Links
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 22
- 239000012736 aqueous medium Substances 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000000605 extraction Methods 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 5
- VFVHNRJEYQGRGE-UHFFFAOYSA-N 3-acetylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(C)=O VFVHNRJEYQGRGE-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- -1 acetyl-β-mercapto-n-butyric acid Chemical compound 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- ODXYWRPJDYJIPT-UHFFFAOYSA-N methyl beta-(acetylthio)isobutyrate Chemical compound COC(=O)C(C)CSC(C)=O ODXYWRPJDYJIPT-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- MHRDCHHESNJQIS-UHFFFAOYSA-N 2-methyl-3-sulfanylpropanoic acid Chemical compound SCC(C)C(O)=O MHRDCHHESNJQIS-UHFFFAOYSA-N 0.000 description 1
- BNKHMNMYQOLXCD-UHFFFAOYSA-N 2-methyl-4-sulfanylbutanoic acid Chemical compound OC(=O)C(C)CCS BNKHMNMYQOLXCD-UHFFFAOYSA-N 0.000 description 1
- BCAYPPFBOJCRPN-UHFFFAOYSA-N 3-benzoylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(=O)C1=CC=CC=C1 BCAYPPFBOJCRPN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 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
- 239000006285 cell suspension Substances 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000009629 microbiological culture Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
【発明の詳細な説明】
本発明は、水性媒体中に含まれる一般式
（式中R1はアルキル基、アラルキル基又はア
リール基、R2及びR3はアルキル基又は水素原子、
ｎは１又は２を示す）で表されるカルボン酸誘導
から光学活性化合物を分離する方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the general formula contained in an aqueous medium. (In the formula, R 1 is an alkyl group, an aralkyl group, or an aryl group, R 2 and R 3 are an alkyl group or a hydrogen atom,
The present invention relates to a method for separating an optically active compound from a carboxylic acid derivative (n represents 1 or 2).
式のカルボン酸誘導体は種々の生理活性物質
を合成するための原料として利用されている。本
発明者らは式のラセミ体エステルを酵素的に不
斉分解することにより、光学活性カルボン酸及び
その対掌体エステルに導く方法を先に提案した
（特開昭60−12992号、60−12993号、60−30692号
及び60−94091号各公報参照）。このように酵素的
に不斉加水分解されて得られた反応液等の水性媒
体中から、式のカルボン酸誘導体を水と混和し
ない溶媒で抽出分離しようとすると、エマルジヨ
ンが生成して抽出が不可能となることが多く、抽
出効率が低いという欠点があつた。 Carboxylic acid derivatives of the formula are used as raw materials for synthesizing various physiologically active substances. The present inventors have previously proposed a method of deriving an optically active carboxylic acid and its enantiomer ester by enzymatically asymmetrically decomposing a racemic ester of the formula (JP-A-60-12992, 60- 12993, 60-30692 and 60-94091). If an attempt is made to extract and separate the carboxylic acid derivative of the formula from an aqueous medium such as a reaction solution obtained by enzymatic asymmetric hydrolysis using a water-immiscible solvent, an emulsion will be formed and the extraction will be unsuccessful. However, the disadvantage was that the extraction efficiency was low.
式の化合物を酵素的に不斉加水分解して得ら
れる水性媒体中には、原料として使用した式の
化合物がかなり多量に残存する場合があり、これ
を有効利用することが要望されていた。本発明は
このエマルジヨンの生成を防いで、生成物及び残
存化合物を効率よく抽出することを目的とする。 In the aqueous medium obtained by enzymatically asymmetric hydrolysis of the compound of the formula, there are cases where a considerable amount of the compound of the formula used as a raw material remains, and there has been a desire to effectively utilize this. The purpose of the present invention is to prevent the formation of this emulsion and efficiently extract the products and residual compounds.
本発明は、一般式
（式中R1はアルキル基、アラルキル基又はア
リール基、R2及びR3はアルキル基又は水素原子、
ｎは１又は２を示す）で表されるカルボン酸誘導
を生体成分を用いて酵素的に加水分解し、得られ
る一般式
（式中R1，R2及びｎは前記の意味を有する）
で表される光学活性カルボン酸とその対掌体エス
テル及び生体成分を含む水性媒体を、PH５以下に
調整したのち、有機溶媒を用いて該光学活性カル
ボン酸とその対掌体エステルを抽出することを特
徴とするカルボン酸誘導体の分離法である。 The present invention is based on the general formula (In the formula, R 1 is an alkyl group, an aralkyl group, or an aryl group, R 2 and R 3 are an alkyl group or a hydrogen atom,
General formula obtained by enzymatically hydrolyzing a carboxylic acid derivative represented by (n represents 1 or 2) using a biological component (In the formula, R 1 , R 2 and n have the above meanings)
After adjusting an aqueous medium containing an optically active carboxylic acid represented by the formula, its enantiomer ester, and a biological component to a pH of 5 or less, extracting the optically active carboxylic acid and its enantiomer ester using an organic solvent. This is a method for separating carboxylic acid derivatives.
エマルジヨン生成は、水性媒体中に混在する生
体成分例えば菌体分解物、蛋白質などに起因して
いる。本発明方法によれば、式の化合物及びそ
の加水分解生成物を抽出するに際して、あらかじ
め水性媒体のPHを５以下に調整するので生体成分
が凝集し、その結果、エマルジヨンの生成を防ぐ
ことができ、効率よく抽出することができる。 Emulsion formation is caused by biological components such as bacterial cell decomposition products and proteins mixed in the aqueous medium. According to the method of the present invention, when extracting the compound of the formula and its hydrolysis product, the pH of the aqueous medium is adjusted to 5 or less in advance, which prevents biological components from coagulating and, as a result, from forming an emulsion. , can be extracted efficiently.
本発明においてカルボン酸誘導体（）の置換
基R1のためのアルキル基としては例えばメチル
基、エチル基など、アラルキル基としては例えば
ベンジル基、アリール基としては例えばフエニル
基、R2のためのアルキル基としては例えばメチ
ル基、エチル基などが挙げられる。カルボン酸誘
導体（）としては、Ｓ−アセチル−β−メルカ
プトイソ酪酸のメチルエステル、Ｓ−アセチル−
γ−メルカプト−α−メチル−ｎ−酪酸のメチル
エステル、Ｓ−ベンゾイル−β−メルカプトイソ
酪酸のメチルエステル、Ｓ−フエニルアセチル−
β−メルカプトイソ酪酸のメチルエステル、Ｓ−
アセチル−β−メルカプト−ｎ−酪酸のメチルエ
ステル等が挙げられる。 In the present invention, examples of the alkyl group for the substituent R 1 of the carboxylic acid derivative () include methyl group, ethyl group, etc., examples of the aralkyl group include benzyl group, examples of the aryl group include phenyl group, and alkyl group for R 2 . Examples of the group include a methyl group and an ethyl group. As the carboxylic acid derivative (), methyl ester of S-acetyl-β-mercaptoisobutyric acid, S-acetyl-
Methyl ester of γ-mercapto-α-methyl-n-butyric acid, methyl ester of S-benzoyl-β-mercaptoisobutyric acid, S-phenylacetyl-
Methyl ester of β-mercaptoisobutyric acid, S-
Examples include methyl ester of acetyl-β-mercapto-n-butyric acid.
生体成分としては例えば微生物菌体、その分解
物、酵素蛋白質等が挙げられる。式の光学活性
カルボン酸とその対掌体エステルと生体成分を含
む水性媒体としては、酵素的な不斉加水分解液例
えば微生物培養液、酵素反応液などが挙げられ
る。 Examples of biological components include microbial cells, decomposed products thereof, enzyme proteins, and the like. Examples of the aqueous medium containing the optically active carboxylic acid of the formula, its enantiomer ester, and biological components include enzymatic asymmetric hydrolysis solutions such as microbial culture solutions and enzymatic reaction solutions.
この水性媒体から式の光学活性カルボン酸と
その対掌体エステルを抽出分離するには、水と混
和しない有機溶媒を用いることが好ましい。水と
混和しない有機溶媒としては、ハロゲン化炭化水
素類例えばクロロホルム、四塩化炭素など、エス
テル類例えば酢酸エチル、エーテル類例えばエチ
ルエーテル、炭化水素類例えばベンゼン、トルエ
ン、シクロヘキサン、ｎ−ヘキサンなどが用いら
れる。 In order to extract and separate the optically active carboxylic acid of formula and its enantiomer ester from this aqueous medium, it is preferable to use an organic solvent that is immiscible with water. Examples of organic solvents that are immiscible with water include halogenated hydrocarbons such as chloroform and carbon tetrachloride, esters such as ethyl acetate, ethers such as ethyl ether, and hydrocarbons such as benzene, toluene, cyclohexane, and n-hexane. It will be done.
本発明を実施するに際しては、式の光学活性
カルボン酸とその対掌体エステルと生体成分を含
む水性媒体のPHを５以下に調整する。PHを調整す
るためには塩酸、硫酸、燐酸などの鉱酸が用いら
れる。水性媒体のPHを５以下にすることによりエ
マルジヨン生成の要因と考えられる蛋白質などの
生体成分が凝集してくる。この凝集物は抽出前に
水性媒体から除去してもよいが、この凝集物を含
む状態で有機溶媒で抽出することもできる。水性
媒体から凝集物を除去した場合は、所望のPHで抽
出操作を行うことができる。なお、凝集物を除去
する方法としては遠心分離、濾過などが用いられ
る。 When carrying out the present invention, the pH of the aqueous medium containing the optically active carboxylic acid of the formula, its enantiomer ester, and biological components is adjusted to 5 or less. Mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid are used to adjust the pH. By lowering the pH of the aqueous medium to 5 or less, biological components such as proteins, which are considered to be a factor in emulsion formation, aggregate. This aggregate may be removed from the aqueous medium before extraction, but it is also possible to extract the aggregate with an organic solvent. When the aggregates are removed from the aqueous medium, the extraction operation can be performed at the desired pH. Note that centrifugation, filtration, etc. are used as a method for removing aggregates.
次いで有機溶媒を用いて式の光学活性カルボ
ン酸とその対掌体エステルを抽出する。抽出法と
しては水性媒体に有機溶媒を加え、よく混合した
のち静置して界面を形成させ、次いで分液する方
法を用いることが好ましい。これにより前記のカ
ルボン酸誘導体は水性媒体から有機溶媒に移行す
る。有機溶媒の使用量は、水性媒体１容量部に対
し、0.01〜100容量部が好ましい。 An organic solvent is then used to extract the optically active carboxylic acid of the formula and its enantiomer ester. As an extraction method, it is preferable to use a method in which an organic solvent is added to an aqueous medium, the mixture is thoroughly mixed, and then left to stand to form an interface, followed by liquid separation. This transfers the carboxylic acid derivative from the aqueous medium to the organic solvent. The amount of organic solvent used is preferably 0.01 to 100 parts by volume per 1 part by volume of the aqueous medium.
なお水性媒体中に混在する光学活性カルボン酸
及びその対掌体エステルを別個に抽出する場合は
水性媒体のPHを５以下にして生成する凝集物を除
去したのち、PHを中性付近に調整して有機溶媒で
抽出し、次いで水性媒体のPHを酸性にして有機溶
媒で抽出すればよい。得られた抽出物は蒸留、カ
ラムクロマトグラフイ等により更に精製すること
もできる。 In addition, when separately extracting the optically active carboxylic acid and its enantiomer ester mixed in the aqueous medium, the pH of the aqueous medium should be lowered to 5 to remove any aggregates formed, and then the pH should be adjusted to around neutrality. Then, the pH of the aqueous medium is made acidic and extraction is performed with an organic solvent. The obtained extract can be further purified by distillation, column chromatography, etc.
本発明方法によれば、従来抽出時にエマルジヨ
ン生成が起こり抽出不可能であつた媒体からも、
カルボン酸誘導体を容易に抽出できる。 According to the method of the present invention, even from a medium that conventionally generates emulsion during extraction and cannot be extracted,
Carboxylic acid derivatives can be easily extracted.
下記実施例中の％は重量％を意味する。 In the following examples, % means weight %.
実施例 １
シユードモナス・フルオレセンス IFO 3081
を肉エキス1.0％、食塩0.5％及びペプトン1.0％か
ら成る液体培地（PH7.2）100mlに植菌し、30℃、
１日間振とう培養を行つた。Example 1 Pseudomonas fluorescens IFO 3081
was inoculated into 100 ml of a liquid medium (PH7.2) consisting of 1.0% meat extract, 0.5% salt, and 1.0% peptone, and incubated at 30°C.
A shaking culture was performed for 1 day.
培養終了後、培養液を遠心分離し、得られた菌
体の全量をイオン交換水で洗浄したのち、Ｍ／10
燐酸緩衝液（PH7.0）50mlに懸濁した。この菌体
懸濁液に（±）−Ｓ−アセチル−β−メルカプト
イソ酪酸メチル2.5mlを加え、30℃で48時間振と
うして反応させた。この反応液をPH２からPH７の
範囲に調整し、酢酸エチルで抽出を試みたとこ
ろ、PHが５より高いものに関してはエマルジヨン
の生成がみられ抽出が不可能であつたが、PHが５
以下のものに関しては水性媒体中の生体成分は凝
集し、Ｓ−アセチル−β−メルカプトイソ酪酸メ
チル及びＳ−アセチル−β−メルカプトイソ酪酸
が容易に抽出された。これに対しPH３で抽出を行
うと、抽出物は1.95g得られた。 After the culture is completed, the culture solution is centrifuged, and the entire amount of bacterial cells obtained is washed with ion-exchanged water.
It was suspended in 50 ml of phosphate buffer (PH7.0). 2.5 ml of methyl (±)-S-acetyl-β-mercaptoisobutyrate was added to this cell suspension, and the mixture was shaken and reacted at 30°C for 48 hours. When this reaction solution was adjusted to a pH range of 2 to 7 and extraction was attempted with ethyl acetate, emulsion formation was observed when the pH was higher than 5 and extraction was impossible;
Regarding the following, the biological components in the aqueous medium were aggregated, and methyl S-acetyl-β-mercaptoisobutyrate and S-acetyl-β-mercaptoisobutyric acid were easily extracted. On the other hand, when extraction was performed with PH3, 1.95g of extract was obtained.
実施例 ２
実施例１で得られた反応終了液のPHを４に調整
し、生体成分の少なくとも一部を凝集させ、遠心
分離して除去し、次いでPHを７に調整してＳ−ア
セチル−β−メルカプトイソ酪農メチルを酢酸エ
チルで抽出した。次いで水層のPHを硫酸で2.0に
下げたのち、水層中のＳ−アセチル−β−メルカ
プトイソ酪酸を酢酸エチルで抽出した。抽出液に
無水硫酸ナトリウムを加えて脱水処理したのち、
溶媒を蒸発除去した。抽出されたＳ−アセチル−
β−メルカプトイソ酪酸は0.91g、Ｓ−アセチル
−β−メルカプトイソ酪酸メチルは1.04gであり、
その比旋光度を測定したところ、光学活性カルボ
ン酸とその対掌体エステルが生成していることが
確認された。この際、反応終了液からの生体成分
の除去を行わず、PHを７に調整して抽出を試みた
ところ、エマルジヨンが生成して、抽出は不可能
であつた。Example 2 The pH of the reaction-completed solution obtained in Example 1 was adjusted to 4, at least a portion of the biological components were aggregated, and removed by centrifugation, and then the pH was adjusted to 7 and S-acetyl- The β-mercaptoisobutyric methyl was extracted with ethyl acetate. Next, the pH of the aqueous layer was lowered to 2.0 with sulfuric acid, and then S-acetyl-β-mercaptoisobutyric acid in the aqueous layer was extracted with ethyl acetate. After adding anhydrous sodium sulfate to the extract and dehydrating it,
The solvent was removed by evaporation. Extracted S-acetyl-
β-mercaptoisobutyric acid is 0.91g, S-acetyl-β-mercaptoisobutyrate methyl is 1.04g,
When its specific optical rotation was measured, it was confirmed that an optically active carboxylic acid and its enantiomer ester were produced. At this time, when extraction was attempted by adjusting the pH to 7 without removing biological components from the reaction-completed liquid, an emulsion was formed and extraction was impossible.
Claims (1)
リール基、R2及びR3はアルキル基又は水素原子、
ｎは１又は２を示す）で表されるカルボン酸誘導
を生体成分を用いて酵素的に加水分解し、得られ
る一般式（） （式中R1，R2及びｎは前記の意味を有する）
で表される光学活性カルボン酸とその対掌体エス
テル及び生体成分を含む水性媒体を、PH５以下に
調整したのち、有機溶媒を用いて該光学活性カル
ボン酸とその対掌体エステルを抽出することを特
徴とする、カルボン酸誘導体の分離法。[Claims] 1 General formula () (In the formula, R 1 is an alkyl group, an aralkyl group, or an aryl group, R 2 and R 3 are an alkyl group or a hydrogen atom,
General formula () obtained by enzymatically hydrolyzing a carboxylic acid derivative represented by (n represents 1 or 2) using a biological component (In the formula, R 1 , R 2 and n have the above meanings)
After adjusting an aqueous medium containing an optically active carboxylic acid represented by the formula, its enantiomer ester, and a biological component to a pH of 5 or less, extracting the optically active carboxylic acid and its enantiomer ester using an organic solvent. A method for separating carboxylic acid derivatives, characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10180384A JPS60248189A (en) | 1984-05-22 | 1984-05-22 | Separation method for carboxylic acid derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10180384A JPS60248189A (en) | 1984-05-22 | 1984-05-22 | Separation method for carboxylic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60248189A JPS60248189A (en) | 1985-12-07 |
| JPH0533994B2 true JPH0533994B2 (en) | 1993-05-20 |
Family
ID=14310295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10180384A Granted JPS60248189A (en) | 1984-05-22 | 1984-05-22 | Separation method for carboxylic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60248189A (en) |
-
1984
- 1984-05-22 JP JP10180384A patent/JPS60248189A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60248189A (en) | 1985-12-07 |
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| Date | Code | Title | Description |
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| LAPS | Cancellation because of no payment of annual fees |