JPH0446119B2 - - Google Patents
Info
- Publication number
- JPH0446119B2 JPH0446119B2 JP3233787A JP3233787A JPH0446119B2 JP H0446119 B2 JPH0446119 B2 JP H0446119B2 JP 3233787 A JP3233787 A JP 3233787A JP 3233787 A JP3233787 A JP 3233787A JP H0446119 B2 JPH0446119 B2 JP H0446119B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- ester
- bacterial cells
- carboxylic acid
- 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
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- 150000002148 esters Chemical class 0.000 claims description 18
- 244000005700 microbiome Species 0.000 claims description 15
- 230000001580 bacterial effect Effects 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 241000588914 Enterobacter Species 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- ODXYWRPJDYJIPT-UHFFFAOYSA-N methyl beta-(acetylthio)isobutyrate Chemical compound COC(=O)C(C)CSC(C)=O ODXYWRPJDYJIPT-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- VFVHNRJEYQGRGE-UHFFFAOYSA-N 3-acetylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(C)=O VFVHNRJEYQGRGE-UHFFFAOYSA-N 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000588697 Enterobacter cloacae Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- -1 methyl β-mercaptoisobutyrate Chemical compound 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZGOICFGZOMREEY-UHFFFAOYSA-N 2-methyl-3-oxo-2-(sulfanylmethyl)butanoic acid Chemical compound CC(=O)C(C)(CS)C(O)=O ZGOICFGZOMREEY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 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
- 239000013543 active substance Substances 0.000 description 1
- 238000005273 aeration Methods 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
- 239000007853 buffer solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 235000013372 meat Nutrition 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 238000004321 preservation Methods 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
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 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
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
【発明の詳細な説明】
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はアルキル基、ｎは１又は２を示す）
で表わされる光学活性カルボン酸及びその対掌体
エステルの製造法に関する。
式のカルボン酸及びその対掌体エステルは光
学活性を有する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。
従来、式の光学活性カルボン酸の製造方法と
しては、予め有機合成的にラセミ体のカルボン酸
を合成したのち、光学分割剤を用いて分割する方
法、すなわち物理化学的に一方の光学活性体とそ
の対掌体とに分別する方法が知られている（特開
昭55−118455号、同56−81557号、同57−188563
号、ヨーロツパ特許公開第79200477号各公報参
照）。一方、光学活性カルボン酸エステルは、カ
ルボン酸を光学分割したのちエステル化反応を行
い、光学活性エステルに導く方法などが採られて
いる。しかし、これらの方法では、高価な分割剤
が多量に必要とされること、この分割剤が不純物
として製品中に混入しやすいこと、分割工程が複
雑であることなどの欠点があり、工業的な製法と
しては必ずしも満足できるものではない。
これらの欠点を改良する方法として、最近、式
で表される光学活性を有するカルボン酸やその
対掌体エステルを微生物の作用により製造する方
法が提案されている（特開昭60−12993号、同60
−30692号、同60−141297号各公報参照）。
本発明者らは、さらに微生物の作用によりDL
−カルボン酸エステルを不斉加水分解する方法に
関して鋭意研究を行つた結果、新たに、エンテロ
バクター（Enterobacter）属の微生物を用いる
ことにより、式で表される光学活性カルボン酸
及びその対掌体エステルを効率よく製造できるこ
とを見出した。
すなわち、本発明は、一般式
（式中R3はアルキル基を示し、R1、R2及びｎは
前記の意味を有する）で表わされるエステルにエ
ステル結合を不斉加水分解する能力を有するエン
テロバクター（Enterobacter）属に属する微生
物の培養液、菌体又は菌体処理物を作用させるこ
とを特徴とする一般式
（式中R1、R2及びｎは前記の意味を有する）で
表わされる光学活性カルボン酸及びその対掌体エ
ステルの製造法である。
式及び式の化合物の置換基R1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、例えばフエニル基が挙げられる。
本発明に用いられる式のエステルとしては、
例えばＳ−アセチル−β−メルカプトイソ酪酸メ
チル、Ｓ−アセチル−γ−メルカプト−α−メチ
ル−ｎ−酪酸メチル、Ｓ−ベンゾイル−β−メル
カプトイソ酪酸メチル、Ｓ−フエニルアセチル−
β−メルカプトイソ酪酸メチルなどが挙げられ
る。これらエステルのＤ−体とＬ−体の混合割合
は特に限定されない。
本発明で用いられる微生物は、エンテロバクタ
ー属に属し、前記の化合物のエステル結合を不斉
加水分解する能力を有する微生物であつて、例え
ばエンテロバクター・クロアツセ
（Enterobacter cloacae）IAM 1624が挙げられ
る。この微生物は公知の微生物であり、東京大学
応用微生物研究所（IAM）の菌株保存機関を通
じて容易に入手することができる。
本発明における微生物の培養は、通常液体培養
で行う。培地としては、微生物が資化し得る炭素
源、窒素源、ビタミン、無機塩類等を適宜使用す
るが、微生物の加水分解能を向上させるために、
エステル等を培地に少量添加することも可能であ
る。培養は微生物が生育可能である温度及びPHで
行われるが、通常、温度５〜50℃、PH２〜11、好
ましくは５〜８の範囲である。微生物の生育を促
進させるために通気撹拌を行つても良い。
加水分解反応を行うに際しては、培養の開始時
又は途中で培地にエステル（式）を添加しても
良く、予め微生物を培養したのち培養液にエステ
ル（式）を添加してもよい。また、増殖した微
生物の菌体を遠心分離等により採取し、これをエ
ステルを含む反応媒体に加えても良い。この場
合、菌体は取り扱い上の便宜から乾燥菌体、例え
ば凍結乾燥菌体、噴霧乾燥菌体又は有機溶媒、例
えばアセトン、トルエン等で処理した菌体、ある
いは菌体破砕物、菌体抽出物等の菌体処理物を用
いることもできる。反応媒体としては、例えばイ
オン交換水又は緩衝液が用いられる。反応媒体又
は培養液中のエステルの濃度は0.01〜50重量％が
好ましい。エステルは水に懸濁した状態で加える
こともできる。また、メタノール、アセトンなど
の有機溶媒を反応液に加えてエステルの溶解性を
向上させることもできる。反応液のPHは２〜11、
好ましくは５〜８の範囲である。反応が進行する
に伴い生成したカルボン酸により反応液のPHが低
下してくるが、この場合は適当な中和剤で最適PH
に維持することが好ましい。反応温度は５〜50℃
が好ましい。
反応液又は培養液からの生成物の分離精製は通
常の方法、例えば抽出、再結晶、カラムクロマト
グラフイ等により行うことができる。
以下、実施例に従つて本発明を詳述する。
なお、下記実施例中の％は特定してない限り重
量％を意味する。
実施例 １
エンテロバクター・クロアツセ
（Enterobacter cloacae）IAM1624を肉エキス
1.0％、ペプトン1.0％およびNaCI0.5％からなる
液体培地（PH7.2）100mlに植菌し、30℃１日間振
盪培養を行つた。培養終了後、培養菌体を全量集
菌し、1/10Ｍりん酸緩衝液（PH７）100ml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２mlを加え、30℃
で48時間振盪して反応させた。反応終了後、反応
液５mlを除菌し高速液体クロマトグラフイーによ
り反応生成物がＳ−アセチル−β−メルカプトイ
ソ酪酸であることを確認した。この時のＳ−アセ
チル−β−メルカプトイソ酪酸メチルの分解率は
48％であつた。
反応液をNaOHでPH7.0に調整し、Ｓ−アセチ
ル−β−メルカプトイソ酪酸メチルを酢酸エチル
で抽出分離した。次いで水層を硫酸でPH2.0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。酢酸エチル
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。分離抽出されたＳ−
アセチル−β−メルカプトイソ酪酸及びＳ−アセ
チル−β−メルカプトイソ酪酸メチルの比旋光度
を日本分光製旋光度計（DIP−360型）で測定し
た。
結果を表１に示す。この表より光学活性カルボ
ン酸とその対掌体エステルが生成していることが
判る。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the general formula (In the formula, R 1 is an alkyl group, an aralkyl group, or an aryl group, R 2 is an alkyl group, and n is 1 or 2)
The present invention relates to a method for producing an optically active carboxylic acid represented by the formula and its enantiomer ester. Carboxylic acids of the formula and their enantiomers are used as raw materials for synthesizing various physiologically active substances with optical activity. Conventionally, the method for producing the optically active carboxylic acid of the formula is to first synthesize a racemic carboxylic acid by organic synthesis and then resolve it using an optical resolving agent. A method of separating the enantiomers is known (JP-A-55-118455, JP-A No. 56-81557, JP-A No. 57-188563).
(see European Patent Publication No. 79200477). On the other hand, optically active carboxylic acid esters are produced by optically resolving carboxylic acids and then subjecting them to an esterification reaction to produce optically active esters. However, these methods have drawbacks such as the need for large quantities of expensive resolving agents, the ease with which these resolving agents are mixed into the product as impurities, and the complexity of the resolving process. The manufacturing method is not necessarily satisfactory. As a method to improve these drawbacks, a method has recently been proposed in which a carboxylic acid having optical activity represented by the formula or its enantiomer ester is produced by the action of microorganisms (Japanese Patent Application Laid-Open No. 12993/1983, Same 60
-30692 and 60-141297). The present inventors further demonstrated that DL due to the action of microorganisms.
- As a result of intensive research on the method of asymmetrically hydrolyzing carboxylic acid esters, we newly discovered the optically active carboxylic acid represented by the formula and its enantiomer ester by using microorganisms of the genus Enterobacter. It was discovered that it is possible to produce efficiently. That is, the present invention provides the general formula A microorganism belonging to the genus Enterobacter that has the ability to asymmetrically hydrolyze an ester bond to an ester represented by the formula (wherein R 3 represents an alkyl group, and R 1 , R 2 and n have the meanings described above) A general formula characterized by the action of a culture solution, bacterial cells, or treated bacterial cells. This is a method for producing an optically active carboxylic acid represented by the formula (wherein R 1 , R 2 and n have the above-mentioned meanings) and its enantiomer ester. Examples of the alkyl group of the substituent R 1 of the formula and the compound of the formula include a methyl group and an ethyl group, examples of the aralkyl group include a benzyl group, and examples of the aryl group include a phenyl group. The esters of the formula used in the present invention include:
For example, methyl S-acetyl-β-mercaptoisobutyrate, methyl S-acetyl-γ-mercapto-α-methyl-n-butyrate, methyl S-benzoyl-β-mercaptoisobutyrate, S-phenylacetyl-
Examples include methyl β-mercaptoisobutyrate. The mixing ratio of the D-form and L-form of these esters is not particularly limited. The microorganism used in the present invention belongs to the genus Enterobacter and has the ability to asymmetrically hydrolyze the ester bond of the above-described compound, and includes, for example, Enterobacter cloacae IAM 1624. This microorganism is a known microorganism and can be easily obtained through the strain preservation facility of the Institute of Applied Microbiology (IAM), the University of Tokyo. The microorganisms in the present invention are usually cultured in liquid culture. As a culture medium, carbon sources, nitrogen sources, vitamins, inorganic salts, etc. that can be assimilated by microorganisms are used as appropriate, but in order to improve the hydrolysis ability of microorganisms,
It is also possible to add small amounts of esters and the like to the medium. Cultivation is carried out at a temperature and pH that allow microorganisms to grow, usually at a temperature of 5 to 50°C and a pH of 2 to 11, preferably 5 to 8. Aeration and stirring may be performed to promote the growth of microorganisms. When carrying out the hydrolysis reaction, the ester (formula) may be added to the medium at the beginning or during the culture, or the ester (formula) may be added to the culture solution after culturing the microorganisms in advance. Alternatively, the cells of the grown microorganism may be collected by centrifugation or the like and added to the reaction medium containing the ester. In this case, for convenience of handling, the bacterial cells are dried bacterial cells, such as freeze-dried bacterial cells, spray-dried bacterial cells, bacterial cells treated with an organic solvent such as acetone or toluene, or crushed bacterial cells, or bacterial cell extracts. It is also possible to use bacterial cell-treated products such as the following. As the reaction medium, for example, ion exchange water or a buffer solution is used. The concentration of ester in the reaction medium or culture solution is preferably 0.01 to 50% by weight. The ester can also be added in suspension in water. Furthermore, the solubility of the ester can be improved by adding an organic solvent such as methanol or acetone to the reaction solution. The pH of the reaction solution is 2-11,
Preferably it is in the range of 5-8. As the reaction progresses, the PH of the reaction solution decreases due to the generated carboxylic acid, but in this case, the optimum PH can be adjusted using an appropriate neutralizing agent.
It is preferable to maintain the Reaction temperature is 5-50℃
is preferred. Separation and purification of the product from the reaction solution or culture solution can be carried out by conventional methods such as extraction, recrystallization, column chromatography, etc. The present invention will be described in detail below with reference to Examples. In addition, % in the following examples means weight % unless otherwise specified. Example 1 Meat extract of Enterobacter cloacae IAM1624
1.0%, peptone 1.0%, and NaCI 0.5% (PH7.2) (100 ml) and cultured with shaking at 30°C for 1 day. After the cultivation was completed, the entire cultured bacterial cells were collected and suspended in 100 ml of 1/10M phosphate buffer (PH7). This bacterial cell suspension contains (±)-S-acetyl-
Add 2 ml of methyl β-mercaptoisobutyrate and cool at 30°C.
The mixture was shaken for 48 hours to react. After the reaction was completed, 5 ml of the reaction solution was sterilized and the reaction product was confirmed to be S-acetyl-β-mercaptoisobutyric acid by high performance liquid chromatography. The decomposition rate of methyl S-acetyl-β-mercaptoisobutyrate at this time is
It was 48%. The reaction solution was adjusted to pH 7.0 with NaOH, and methyl S-acetyl-β-mercaptoisobutyrate was extracted and separated with ethyl acetate. Next, the aqueous layer was lowered to pH 2.0 with sulfuric acid, and then S-acetyl-β-mercaptoisobutyric acid in the aqueous layer was extracted with ethyl acetate. Anhydrous sodium sulfate was added to the ethyl acetate extract for dehydration, and then the solvent was removed by evaporation. Separated and extracted S-
The specific optical rotations of acetyl-β-mercaptoisobutyric acid and methyl S-acetyl-β-mercaptoisobutyrate were measured using a polarimeter (Model DIP-360) manufactured by JASCO Corporation. The results are shown in Table 1. From this table, it can be seen that optically active carboxylic acid and its enantiomer ester were produced. 【table】
Claims (1)
ール基、R2及びR3はアルキル基、ｎは１又は２
を示す）で表わされるエステルに、エステル結合
を不斉加水分解する能力を有するエンテロバクタ
ー（Enterobacter）属に属する微生物の培養液、
菌体又は菌体処理物を作用させることを特徴とす
る、一般式 （式中R1、R2及びｎは前記の意味を有する）で
表わされる光学活性カルボン酸及びその対掌体エ
ステルの製造法。[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, and n is 1 or 2
A culture solution of a microorganism belonging to the genus Enterobacter that has the ability to asymmetrically hydrolyze an ester bond to an ester represented by
A general formula characterized by the action of bacterial cells or treated bacterial cells. A method for producing an optically active carboxylic acid represented by the formula (wherein R 1 , R 2 and n have the above-mentioned meanings) and its enantiomer ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3233787A JPS63202397A (en) | 1987-02-17 | 1987-02-17 | Method for producing optically active carboxylic acid and its enantiomer ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3233787A JPS63202397A (en) | 1987-02-17 | 1987-02-17 | Method for producing optically active carboxylic acid and its enantiomer ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63202397A JPS63202397A (en) | 1988-08-22 |
| JPH0446119B2 true JPH0446119B2 (en) | 1992-07-28 |
Family
ID=12356134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3233787A Granted JPS63202397A (en) | 1987-02-17 | 1987-02-17 | Method for producing optically active carboxylic acid and its enantiomer ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63202397A (en) |
-
1987
- 1987-02-17 JP JP3233787A patent/JPS63202397A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63202397A (en) | 1988-08-22 |
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