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Enzyme directed diastereoselectivity in chemical reductions: studies towards the preparation of all four isomers of 1-phenyl-1,3-butanediol

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Title Enzyme directed diastereoselectivity in chemical reductions: studies towards the preparation of all four isomers of 1-phenyl-1,3-butanediol
 
Creator Ahmad, K.
Koul, S.
Taneja, S.C.
Singh, A.P.
Kapoor, M.
Riyaz, Hassan
Verma, V.
Qazi, G.N.
 
Subject Biological Sciences
Chemical Sciences
 
Description Enzymes play an important role in guiding the diastereoselectivity of the final products during the chemical reduction of the intermediates (R)- and (S)-3-hydroxy-1-phenyl-1-butanone, prepared by bioreduction of 1-phenyl-1,3-butadione. For example,the presence of an oxidoreductase such as Pichia capsulata during a one pot, two step, enzymo-chemical reduction of 1-phenyl-1,3-
butadione produced corresponding (1R,3S)-1-phenyl-1,3-butanediol (de�98%), similarly Zygosaccharomyces rouxii furnished(1S,3R)-1-phenyl-1,3-butanediol (de�98%). On the other hand chemical reduction of (R)- and (S)-3-hydroxy-1-phenyl-1-butanone after the exclusion of the enzymes resulted in complete loss of diastereoselectivity, leading to the formation of all four isomers of
1-phenyl-1,3-butanediol. Moreover the yields of the final products are higher in the one-pot transformations than in the two step sequential reactions.
 
Date 2004
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://iiim.csircentral.net/371/3/10.1016j.tetasy.2004.04.022.pdf
Ahmad, K. and Koul, S. and Taneja, S.C. and Singh, A.P. and Kapoor, M. and Riyaz, Hassan and Verma, V. and Qazi, G.N. (2004) Enzyme directed diastereoselectivity in chemical reductions: studies towards the preparation of all four isomers of 1-phenyl-1,3-butanediol. Tetrahedron: Asymmetry, 15 (11). pp. 1685-1692. ISSN 09574166
 
Relation http://dx.doi.org/10.1016/j.tetasy.2004.04.022
http://iiim.csircentral.net/371/