Toshio Suzuki, H. Idogaki, N. Kasai
1999
Citations
2
Influential Citations
24
Citations
Journal
Enzyme and Microbial Technology
Abstract
Abstract An efficient and practical procedure for simultaneous generation of highly pure methyl ( R )-4-chloro-3-hydroxybutyrate and ( S )-3-hydroxy-γ-butyrolactone using bacterial cells of Enterobacter sp. DS-S-75 was developed. The resulting methyl ( R )-4-chloro-3-hydroxybutyrate from the racemate (8% w/v) exhibited high optical purity (>99% enantiomeric excess) with a yield of 48%. Another of the dual products, ( S )-3-hydroxy-γ-butyrolactone, was also obtained with excellent optical purity (95.9% enantiomeric excess) in a high mole conversion yield of 48%. This conversion of methyl ( S )-4-chloro-3-hydroxybutyrate into ( S )-3-hydroxy-γ-butyrolactone by the resting cells of the strain DS-S-75 proceeded with the complete stereoselectivity releasing chloride ion and methanol; namely, no dechlorinating activity for methyl ( R )-4-chloro-3-hydroxybutyrate was detected. The cellfree extracts from the strain DS-S-75 showed dechlorinating activity for several alkyl ( S )-4-chloro-3-hydroxybutyrates to give ( S )-3-hydroxy-γ-butyrolactone, but not for chlorohydrins, chloroacetone, and chloroacids.