Enzymatic Preparation of Both Enantiomers of 4,4,4-Trifluoro-3-(Indole-3-)Butyric Acid, a Novel Plant Growth Regulator

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概要

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• Efficient optical resolution of both enantiomers of 4,4,4- trifluoro-3-(indole-3-)butyric acid (TFIBA), a novel plant growth regulator, was achieved by two enzyme-catalyzed steps using lipase AK (a lipase from Pseudomonas sp.). S-(+)-TFIBA and R-(-)-TFIBA ethyl ester were prepared with 98% e.e. by the first step of lipase-catalyzed enantioselective hydrolysis in a 0.1 M acetate buffer (pH 5.0) containing 10% t-BuOH at 55℃ for 45 h. The % e.e. in S-(+)-TFIBA was further improved to >99% e.e. by lipase-catalyzed enantiose-lective esterification with ethanol in heptane and subsequent hydrolysis using PLE-A (an esterase from pig liver). R-(-)-TFIBA was prepared with >99% e.e. by the second step of lipase-catalyzed enantioselective hydrolysis under the same conditions as described above and subsequent hydrolysis using PLE-A. The root growth-promoting activity of S-(+)-TFIBA was about 10-fold higher than that R-(-)-TFIBA for black matpe, Chinese cabbage, lettuce, and rice plants (Ohgonbare and Tan-ginbozu).

• 社団法人日本生物工学会の論文
• 1993-09-25

著者

• KATO Katsuya

  National Institute of Advanced Industrial Science and Technology (AIST)

• FUJII SHOZO

  Department of Chemistry, National Industrial Research Institute of Nagoya

• Fujii Shozo

  Department Of Chemistry National Industrial Research Institute Of Nagoya

• Kimoto H

  National Institute Of Advanced Industrial Scienec And Technology (aist)

• Kato Katsuya

  National Industrial Research Insitute Of Nagoya

• KATO KATSUYA

  Chemistry Department, Government Industrial Research Institute

• KATAYAMA MASATO

  Chemistry Department, Government Industrial Research Institute

• GAUTAM RAKESH

  Chemistry Department, Government Industrial Research Institute

• FUJII SHOZO

  Chemistry Department, Government Industrial Research Institute

• KIMOTO HIROSHI

  Chemistry Department, Government Industrial Research Institute

• Katayama M

  Cooperative Research Laboratory For Plant Growth Regulator Development National Institute Of Advance

• Kato K

  National Institute Of Advanced Industrial Science And Technology (aist)

• Gautam R

  Laboratory Of Bioorganic Chemistry Department Of Chemistry National Industrial Research Institute Of

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