OPTICALLY-ACTIVE CHLOROHYDRINS AS CHIRAL C3 AND C4 BUILDING UNITS - MICROBIAL RESOLUTION AND SYNTHETIC APPLICATIONS

Production of highly optically active C3 and C4 chlorohydrins was deve loped by using the bacteria stereoselectively dehalogenating and assim ilating the racemic substrate: Pseudomonas sp. and Alcaligenes sp. The se bacteria stereoselectively assimilate (RS)-2,3-dichloro-1-propanol (DCP) and (RS)-3-chloro-1,2-propanediol (CPD) followed by microbial pr eparation of (R)- and (S)-DCP, and (R)- and (S)-CPD with >99% ee. A no vel dehalogenating enzyme, halohydrin dehydro-dehalogenase from one of the above strains, Alcaligenes sp. DS-S-7G, was applicable for prepar ation of optically active 1,2-diols with 60-99% ee. Moreover, microbia l resolution of C4 chlorohydrins with whole cells of Pseudomonas sp. w as carried out. This resolution reaction using the resting cells gave (R)- and (S)-4-chloro-3-hydroxybutyrate (CHB) and (S)-4-chloro-3-hydro xybutyronitrile CBN) with >98% ee. In the case of the resting cells of Enterobacter sp., both (R)-CHB (>99% eel and (S)-3-hydroxy-gamma-buty rolactone (95% eel with excellent yield were obtained. Also, some typi cal synthetic applications using the above chiral C3 and C4 synthons w ere introduced: ferroelectric liquid crystals, optically active beta-b lockers, and other chiral pharmaceuticals. (C) 1998 Wiley-Liss, Inc.