Enzymatic preparation of optically active 3-trimethylsilylalanine |
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Authors: | H Yamanaka T Fukui T Kawamoto A Tanaka |
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Institution: | (1) Laboratory of Applied Biological Chemistry, Department of Synthetic Chemistry and Biological Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-01, Japan. Fax: +81 75 753 5534, JP |
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Abstract: | We constructed an efficient system for preparing optically active 3-trimethylsilylalanine (TMS-Ala) by kinetic resolution
with acylase I (aminoacylase; N-acylamino-acid amidohydrolase, EC 3.5.1.14). Racemic TMS-Ala was chemically synthesized and acetylated. Enantioselective
deacetylation of N-acetyl-DL-TMS-Ala with acylase I from porcine kidney or from Aspergillus melleus was then attempted. Both enzymes could catalyze the deacetylation of N-acetyl-DL-TMS-Ala, and the porcine enzyme was found to have much higher activity than the enzyme from A. melleus. The optimum pH of the porcine-acylase-catalyzed reaction was 7.5, and the addition of 0.5 mM Co2+ accelerated the reaction. Optically pure L-TMS-Ala (>99% enantiomeric excess, ee) was obtained in 72% yield under the optimized conditions. Furthermore, highly optically
pure D-TMS-Ala (96% ee) could also be obtained in 76% yield by chemically hydrolyzing the residual substrate.
Received: 6 June 1995/Received revision: 3 July 1995/Accepted: 19 July 1995 |
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