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

IR@IIIM: CSIR-Indian Institute of Integrative Medicine, Jammu


Field	Value

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/