Two classes of enzymes of opposite stereochemistry in an organism: One for fluorinated and another for nonfluorinated substrates

T Matsuda, T Harada, N Nakajima, T Itoh…

Index: Matsuda, Tomoko; Harada, Tadao; Nakajima, Nobuyoshi; Itoh, Toshiyuki; Nakamura, Kaoru Journal of Organic Chemistry, 2000 , vol. 65, # 1 p. 157 - 163

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Citation Number: 77

Abstract

Reduction of methyl ketones by dried cells of Geotrichum candidum (APG4) afforded (S)- alcohols in excellent enantiomeric excess (ee), whereas the reduction of trifluoromethyl ketones gave the corresponding alcohols of the opposite configuration also in excellent ee. The replacement of the methyl moiety with a trifluoromethyl group alters both the bulkiness and the electronic properties, the effect of which on the stereoselectivity was examined. ...