PRODUCTION METHOD OF OPTICALLY ACTIVE 3,3-DIFLUORO LACTIC ACID DERIVATIVES

• Main Authors: NISHII TETSURO, ISHII SHOKO, ISHII AKIHIRO, SAWAI NAOKI
• Format: Patent
• Language: English; Japanese
• Published: 19.11.2015
• Subjects: BEER; BIOCHEMISTRY; CHEMISTRY; ENZYMOLOGY; FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE; METALLURGY; MICROBIOLOGY; MUTATION OR GENETIC ENGINEERING; SPIRITS; VINEGAR; WINE

PROBLEM TO BE SOLVED: To provide a method for simply and industrially producing optically active 3,3-difluoro lactic acid derivatives.SOLUTION: Racemic 3,3-difluoro-2-acyl lactate or 3,3-difluoro-2-acyl lactate with a low optical purity is added into a phosphate buffer to make an enzyme, preferably lipase, contact with the ester. Thereby, optically active 3,3-difluoro lactic acid derivatives in which either one of an acyl site or an ester site is hydrolyzed, and optical isomers of 3,3-difluoro-2-acyl lactate which did not react with the enzyme are produced together. Optically active 3,3-difluoro lactic acid can be obtained by separation of either of these chemical species from a reaction mixture, and further hydrolysis in acid conditions. 【課題】簡便で工業的な光学活性３，３−ジフルオロ乳酸誘導体の製造方法を提供する。【解決手段】ラセミ又は光学純度の低い３，３−ジフルオロ−２−アシル乳酸エステルをリン酸緩衝液中に添加し、該エステルに酵素として、好ましくはリパーゼを接触させる。それにより、アシル部位とエステル部位の一方が加水分解された光学活性３，３−ジフルオロ乳酸誘導体、および、酵素と反応しなかった３，３−ジフルオロ−２−アシル乳酸エステルの光学異性体が併産される。反応混合物から、これらのいずれかの化学種を取り出し、さらに酸性条件での加水分解に付せば、光学活性３,３-ジフルオロ乳酸を得ることができる。【選択図】なし