JPH01247100A - Production of optically active carboxylic acid derivative - Google Patents
Production of optically active carboxylic acid derivativeInfo
- Publication number
- JPH01247100A JPH01247100A JP7747688A JP7747688A JPH01247100A JP H01247100 A JPH01247100 A JP H01247100A JP 7747688 A JP7747688 A JP 7747688A JP 7747688 A JP7747688 A JP 7747688A JP H01247100 A JPH01247100 A JP H01247100A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- acid ester
- acyloxycarboxylic
- enzyme
- general formula
- 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.)
- Pending
Links
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 102000004190 Enzymes Human genes 0.000 claims abstract description 20
- 108090000790 Enzymes Proteins 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 17
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 108090001060 Lipase Proteins 0.000 claims abstract description 10
- 102000004882 Lipase Human genes 0.000 claims abstract description 10
- 239000004367 Lipase Substances 0.000 claims abstract description 10
- 235000019421 lipase Nutrition 0.000 claims abstract description 10
- 230000003287 optical effect Effects 0.000 claims abstract description 10
- 108010055297 Sterol Esterase Proteins 0.000 claims abstract description 7
- 102000000019 Sterol Esterase Human genes 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- NWCHELUCVWSRRS-SECBINFHSA-N (2r)-2-hydroxy-2-phenylpropanoic acid Chemical compound OC(=O)[C@@](O)(C)C1=CC=CC=C1 NWCHELUCVWSRRS-SECBINFHSA-N 0.000 description 1
- PPKAIMDMNWBOKN-UHFFFAOYSA-N 2-Oxo-4-phenylbutyric acid Chemical class OC(=O)C(=O)CCC1=CC=CC=C1 PPKAIMDMNWBOKN-UHFFFAOYSA-N 0.000 description 1
- JNJCEALGCZSIGB-UHFFFAOYSA-N 2-hydroxy-4-phenylbutanoic acid Chemical compound OC(=O)C(O)CCC1=CC=CC=C1 JNJCEALGCZSIGB-UHFFFAOYSA-N 0.000 description 1
- JZWSJKRJDWHVBS-UHFFFAOYSA-N 2-hydroxy-5-phenylpentanoic acid Chemical compound OC(=O)C(O)CCCC1=CC=CC=C1 JZWSJKRJDWHVBS-UHFFFAOYSA-N 0.000 description 1
- LNSWZXFVGLLXKC-UHFFFAOYSA-N 6-phenylhexan-2-ol Chemical compound CC(O)CCCCC1=CC=CC=C1 LNSWZXFVGLLXKC-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 239000000872 buffer Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZQAFRVDJBKTTLA-UHFFFAOYSA-N ethyl 2-acetyloxy-4-phenylbutanoate Chemical compound CCOC(=O)C(OC(C)=O)CCC1=CC=CC=C1 ZQAFRVDJBKTTLA-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は光学活性２−ヒドロキシカルボン酸エステル及
びこれとは反対の光学活性を有する２−アシルオキシカ
ルボン酸エステルの製造方法に関する。更に詳しくは、
一般式（Ｉ）（式中、ｐｌ、 Ｒ＊は置換基を有する、
あるいは存しないアルキル基、ｎ＝０〜４の整数を表す
）で表される２−アシルオキシカルボン酸エステルのラ
セミ体に２−アシルオキシ基を不斉加水分解する能力を
有する酵素を作用させ、生成する一般式（ＩＩ）
Ｈ
（式中、Ｒｚは置換基を有する、あるいは有しないアル
キル基、ｎ＝０〜４の整数を表す）で表される光学活性
２−ヒドロキシカルボン酸エステルと、これとは反対の
光学活性を有し、残存する一般式（Ｉ）で表される光学
活性２−アシルオキシカルボン酸エステルとを分離採取
することを特徴とする光学活性カルボン酸誘導体の製造
方法に関する。これらの光学活性化合物は各種医農薬の
合成中間体として重要である。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a process for producing optically active 2-hydroxycarboxylic acid esters and 2-acyloxycarboxylic acid esters having the opposite optical activity. For more details,
General formula (I) (wherein, pl, R* have a substituent,
Alternatively, an enzyme capable of asymmetrically hydrolyzing a 2-acyloxy group is reacted with a racemic form of a 2-acyloxycarboxylic acid ester represented by a non-existing alkyl group (n = an integer of 0 to 4) to generate the product. What is an optically active 2-hydroxycarboxylic acid ester represented by the general formula (II) H (wherein Rz is an alkyl group with or without a substituent, and n = an integer of 0 to 4)? The present invention relates to a method for producing an optically active carboxylic acid derivative, which comprises separating and collecting the remaining optically active 2-acyloxycarboxylic acid ester represented by the general formula (I) having the opposite optical activity. These optically active compounds are important as synthetic intermediates for various medicines and agrochemicals.
〔従来の技術及び発明が解、決しようとする課題〕−一
般式ＩＩ）で表される化合物の遊離酸の光学活性体の製
造方法としては、従来光学活性なセリンから光学活性な
グリシド酸を経て合成する方法（特開昭６２−２１２３
２９号公報）及び２−ケト−４−フェニル酪酸誘導体の
化学的不斉還元による方法（Ｈｕｒ、Ｐａｔ、 ｔ！Ｐ
２Ｏ６９９３）等が知られている。しかしながら、これ
らの方法は高価な光学活性化合物を原料としたり、反応
工程が長く複雑であったり、必ずしも工業的に優れた方
法とは言い難い。また一般式（Ｉ）で表される化合物の
光学活性体の製造法は知られていない。[Problems to be solved by the prior art and the invention] - As a method for producing an optically active form of the free acid of the compound represented by the general formula II), conventionally, optically active glycidic acid is produced from optically active serine. (Japanese Unexamined Patent Publication No. 62-2123
29) and a method by chemical asymmetric reduction of 2-keto-4-phenylbutyric acid derivatives (Hur, Pat, t!P)
2O6993) etc. are known. However, these methods use expensive optically active compounds as raw materials, require long and complicated reaction steps, and are not necessarily industrially superior methods. Further, there is no known method for producing an optically active form of the compound represented by the general formula (I).
かかる事情に鑑み、本発明者らは、前記一般式（ＩＩ）
で表される２−ヒドロキシカルボン酸エステルの光学活
性体及びこれとは反対の光学活性を有し一般式（Ｉ）で
表される２−アシルオキシカルボン酸エステルの光学活
性体の工業的製造法を開発すべく鋭意検討を行った。そ
の結果、各種のリパーゼ、コレステロールエステラーゼ
等の２−アシルオキシ基を不斉加水分解する能力を有す
る酵素が一般式（Ｉ）で表される２−アシルオキシカル
ボン酸エステルの２−アシルオキシ基を極めて効率良く
不斉加水分解し、高い光学純度の一般式（ＩＩ）で表さ
れる２−ヒドロキシカルボン酸エステルの光学活性体及
びこれとは反対の光学活性を有し一般式（Ｉ）で表され
る２−アシルオキシカルボン酸エステルの光学活性体を
与えることを見出し本発明を完成するに至った。In view of such circumstances, the present inventors have developed the general formula (II)
An optically active form of a 2-hydroxycarboxylic acid ester represented by We conducted extensive research to develop this technology. As a result, enzymes capable of asymmetrically hydrolyzing 2-acyloxy groups, such as various lipases and cholesterol esterases, can efficiently hydrolyze the 2-acyloxy groups of 2-acyloxycarboxylic acid esters represented by general formula (I). An optically active form of 2-hydroxycarboxylic acid ester represented by the general formula (II) which is asymmetrically hydrolyzed and has high optical purity, and a 2-hydroxycarboxylic acid ester having the opposite optical activity and represented by the general formula (I). - It was discovered that an optically active form of acyloxycarboxylic acid ester could be obtained, and the present invention was completed.
即ち、本発明は一般式（Ｉ）で表される２−アシルオキ
シカルボン酸エステルのラセミ体に２−アシルオキシ基
を不斉加水分解する能力を有する酵素を作用させ、２−
アシルオキシ基を不斉加水分解し一般式（ＩＩ）で表さ
れる２−ヒドロキシカルボン酸エステルの光学活性体、
及びこれとは反対の光学活性を有し一般式（Ｉ）で表さ
れる２−アシルオキシカルボン酸エステルの光学活性体
を分離採取することを特徴とする光学活性カルボン酸誘
導体の製造方法を提供するものである。That is, in the present invention, an enzyme having the ability to asymmetrically hydrolyze a 2-acyloxy group is reacted with a racemic 2-acyloxycarboxylic acid ester represented by the general formula (I) to produce 2-acyloxycarboxylic acid ester.
An optically active form of 2-hydroxycarboxylic acid ester represented by general formula (II) obtained by asymmetric hydrolysis of an acyloxy group,
and a method for producing an optically active carboxylic acid derivative, which comprises separating and collecting an optically active form of a 2-acyloxycarboxylic acid ester having the opposite optical activity and represented by the general formula (I). It is something.
本発明に用いられる一般式（Ｉ）で表される２−アシル
オキシカルボン酸エステルに於いて、ＲＩ、 Ｒ１で表
されるアルキル基の具体例としては、メチル基、エチル
基、プロピル基、イソプロピル基、ベンジル基等を挙げ
ることができる。また、基本骨格を成す２−ヒドロキシ
カルボン酸の具体例としては、マンデル酸、フェニル乳
酸、２−ヒドロキシ−４−フェニル酪酸、２−ヒドロキ
シ−５−フェニル吉草酸、２−ヒドロキシ−６−フェニ
ルヘキサン酸を挙げることができる。In the 2-acyloxycarboxylic acid ester represented by the general formula (I) used in the present invention, specific examples of the alkyl group represented by RI and R1 include a methyl group, an ethyl group, a propyl group, and an isopropyl group. , benzyl group, etc. Specific examples of 2-hydroxycarboxylic acids forming the basic skeleton include mandelic acid, phenyl lactic acid, 2-hydroxy-4-phenylbutyric acid, 2-hydroxy-5-phenylvaleric acid, and 2-hydroxy-6-phenylhexane. Acids may be mentioned.
また、本発明で用いられる２−アシルオキシ基を不斉加
水分解する能力を有する酵素としては、リパーゼ、コレ
ステロールエステラーゼ等が挙げられる。これらの酵素
は目的とする能力を有するものであればどのような起源
のものでもよいが、好適な例としては、キャンディダ・
シリンドラセア（Ｃａｎｄｉｄａ ｃｙｌｉ−ｎｄｒａ
ｃｅａ）由来のリパーゼＭＹ （泡糊産業製）、リパー
ゼＡＹ ｒアマノ」３０（天野製薬製）、リパーゼ（生
化学工業製）、ＩＪパーゼ（ベーリンガーハイム製）、
リパーゼ タイプ■（シグマ製）、リパーゼ（牛丼化学
製）、コレステロールエステラーゼ（生化学工業製）、
コレステロールエステラーゼ（ベーリンガー・マンハイ
ム山の内装）、アスペルギルス・ニガー（Ａｓｐｅｒｇ
ｉｌｌｕｓ ｎｉｇａｒ）由来のすバーゼＡ 「アマノ
」６（天野製薬製）、豚肝臓由来のエステラーゼ（シグ
マ類）等を挙げることができる。これらの酵素は、精製
酵素、粗酵素、酵素剤としての微生物菌体、あるいは、
培養液そのまま等、いずれの形態でも必要に応じて用い
ることができる。また、これらの酵素は、それぞれ単独
でも、あるいは必要に応じて混合して用いることもでき
る。また、これらを常法により固定化して用いることも
できる。Further, examples of the enzyme having the ability to asymmetrically hydrolyze a 2-acyloxy group used in the present invention include lipase, cholesterol esterase, and the like. These enzymes may be of any origin as long as they have the desired ability, but a suitable example is Candida.
Cylindracea (Candida cyli-ndra)
cea) derived lipase MY (manufactured by Awa-Nori Sangyo), Lipase AY r Amano' 30 (manufactured by Amano Pharmaceutical), lipase (manufactured by Seikagaku Corporation), IJpase (manufactured by Boehringerheim),
Lipase type ■ (manufactured by Sigma), lipase (manufactured by Gyudon Kagaku), cholesterol esterase (manufactured by Seikagaku Corporation),
Cholesterol esterase (Interior of Boehringer Mannheim Mountain), Aspergillus niger (Aspergillus
Subase A "Amano" 6 (manufactured by Amano Pharmaceutical Co., Ltd.) derived from P. illus nigar, esterase derived from pig liver (Sigma type), and the like. These enzymes are purified enzymes, crude enzymes, microbial cells as enzyme agents, or
It can be used in any form as needed, such as as a culture solution as it is. Further, these enzymes can be used alone or in combination as necessary. Moreover, these can also be used after being immobilized by a conventional method.
加水分解反応を行うに際しては、反応液のｐＨを使用す
る酵素の最適ｐＨに合わせて行うのが好ましく、この為
に、適当な緩衝液を用いても良いし、カセイソーダ、カ
セイカリ等の水溶液を用い、ｐＨスタットにより反応中
のｐｉをコントロールしても良い。反応温度も用いる酵
素により異なるが、通常、１０〜６０°Ｃの範囲、好ま
しくは、２５〜５０℃で行われる０反応液中の基質濃度
は、通常、０．１〜５０重量％、好ましくは、５〜３０
重量％で行われる。また、反応液中の酵素濃度は、それ
ぞれの酵素標品の酵素活性に応じて決めることができる
が、例えば０．１〜１０重量％を例示することができる
。反応は、撹拌下、あるいは静置下いずれの方法でも行
うことができるが、好ましくは撹拌下で行われる。反応
終了後は、反応液に適当な有機溶剤、例えば、酢酸エチ
ルｎ−ヘキサン、２−プロパツール等を加え、生成物を
抽出した後、カラムクロマトグラフィー等を用いて常法
により、一般式（ＩＩ）で表される２−ヒドロキシカル
ボン酸エステルの光学活性体、及びこれとは反対の光学
活性を有し一般式（Ｉ）で表される２−アシルオキシカ
ルボン酸エステルの光学活性体を分離精製することがで
きる。When performing a hydrolysis reaction, it is preferable to adjust the pH of the reaction solution to the optimum pH of the enzyme used. For this purpose, an appropriate buffer may be used, or an aqueous solution of caustic soda, caustic potash, etc. , pi during the reaction may be controlled by a pH stat. The reaction temperature also varies depending on the enzyme used, but is usually carried out at a temperature in the range of 10 to 60°C, preferably 25 to 50°C.The substrate concentration in the reaction solution is usually 0.1 to 50% by weight, preferably , 5-30
It is carried out in % by weight. Further, the enzyme concentration in the reaction solution can be determined depending on the enzyme activity of each enzyme preparation, and can be, for example, 0.1 to 10% by weight. The reaction can be carried out either under stirring or while standing still, but is preferably carried out under stirring. After the reaction is completed, a suitable organic solvent such as ethyl acetate n-hexane, 2-propanol, etc. is added to the reaction solution, the product is extracted, and then the product is converted to the general formula ( Separation and purification of the optically active form of the 2-hydroxycarboxylic acid ester represented by II) and the optically active form of the 2-acyloxycarboxylic acid ester having the opposite optical activity and represented by the general formula (I) can do.
以下、本発明を実施例を挙げて更に詳細に説明するが、
本発明はこれらの実施例により限定されるものではない
。Hereinafter, the present invention will be explained in more detail with reference to examples.
The present invention is not limited to these examples.
実施例１
直径２１ｍ−の試験管に表１に示すリパーゼ０．２ｇ、
あるいはコレステロールエステラーゼ０．０１ｇ ヲ取
り、０．２Ｍリン酸緩衝液（ｐＨ７，５） ５ ｗ、２
−アセトキシ−４−フェニル酪酸エチルエステル０．３
ｇを加え、３０°Ｃで６時間振盪した。反応終了後、反
応液の一定量を取り、等量の飽和塩化ナトリウム水溶液
、及び２倍量の有機溶剤（ｎ−ヘキサン／２−プロパツ
ール＝１１）を加え反応生成物を抽出した。この抽出液
を光学分割カラムを用いた高速液体クロマトグラフィー
（カラム：ダイセル化学工業製キラルセルＯＢ、溶媒：
ｎ−ヘキサン／２−プロパツール＝９：１）により反応
生成物を分析、定量し、反応収率、絶対配置及び光学純
度を求めた。Example 1 0.2 g of lipase shown in Table 1 was placed in a test tube with a diameter of 21 m.
Alternatively, remove 0.01g of cholesterol esterase and add 0.2M phosphate buffer (pH 7.5) 5w, 2
-acetoxy-4-phenylbutyric acid ethyl ester 0.3
g and shaken at 30°C for 6 hours. After the reaction was completed, a certain amount of the reaction solution was taken, and an equal amount of saturated aqueous sodium chloride solution and twice the amount of an organic solvent (n-hexane/2-propatol = 11) were added to extract the reaction product. This extract was subjected to high performance liquid chromatography using an optical resolution column (column: Chiralcel OB manufactured by Daicel Chemical Industries, solvent:
The reaction product was analyzed and quantified using n-hexane/2-propertool=9:1), and the reaction yield, absolute configuration, and optical purity were determined.
得られた結果を表１に示す。The results obtained are shown in Table 1.
表 １Table 1
Claims (1)
しないアルキル基、ｎ＝０〜４の整数を表す） で表される２−アシルオキシカルボン酸エステルのラセ
ミ体に２−アシルオキシ基を不斉加水分解する能力を有
する酵素を作用させ、生成する一般式（II） ▲数式、化学式、表等があります▼（II） （式中、Ｒ＾２は置換基を有する、あるいは有しないア
ルキル基、ｎ＝０〜４の整数を表す）で表される光学活
性２−ヒドロキシカルボン酸エステルと、これとは反対
の光学活性を有し、残存する一般式（ I ）で表される
光学活性２−アシルオキシカルボン酸エステルとを分離
採取することを特徴とする光学活性カルボン酸誘導体の
製造方法。 ２、酵素として、リパーゼ又はコレステロールエステラ
ーゼを用いる請求項１記載の製造方法。[Claims] 1. General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) (In the formula, R^1 and R^2 are alkyl groups with or without substituents, n = represents an integer from 0 to 4) General formula (II) produced by reacting an enzyme capable of asymmetrically hydrolyzing a 2-acyloxy group to a racemic form of 2-acyloxycarboxylic acid ester represented by ▲Math. , chemical formulas, tables, etc. ▼(II) (In the formula, R^2 is an alkyl group with or without a substituent, and n = an integer from 0 to 4) Optically active 2-hydroxycarbon An optically active carboxylic acid derivative characterized in that the acid ester and the remaining optically active 2-acyloxycarboxylic ester having the opposite optical activity and represented by the general formula (I) are separated and collected. Production method. 2. The production method according to claim 1, wherein lipase or cholesterol esterase is used as the enzyme.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7747688A JPH01247100A (en) | 1988-03-30 | 1988-03-30 | Production of optically active carboxylic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7747688A JPH01247100A (en) | 1988-03-30 | 1988-03-30 | Production of optically active carboxylic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01247100A true JPH01247100A (en) | 1989-10-02 |
Family
ID=13635038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7747688A Pending JPH01247100A (en) | 1988-03-30 | 1988-03-30 | Production of optically active carboxylic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01247100A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5248610A (en) * | 1990-05-31 | 1993-09-28 | Chisso Corporation | Process for producing optically active α-hydroxyesters using lipase PS |
| US5776766A (en) * | 1995-05-29 | 1998-07-07 | Daiso Co., Ltd. | Optical resolution of chlorohydrin with microorganism |
-
1988
- 1988-03-30 JP JP7747688A patent/JPH01247100A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5248610A (en) * | 1990-05-31 | 1993-09-28 | Chisso Corporation | Process for producing optically active α-hydroxyesters using lipase PS |
| US5776766A (en) * | 1995-05-29 | 1998-07-07 | Daiso Co., Ltd. | Optical resolution of chlorohydrin with microorganism |
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