Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-Phenylethanols

Leandro H. Andrade; Roberta Polak; Andre L. M. Porto; Iracema H. Schoenlein-Crusius; Joao V. Comasseto

doi:10.2174/157017806778559509

ISSN: 1570-1786
E-ISSN: 1875-6255

Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-Phenylethanols
Authors: Leandro H. Andrade¹, Roberta Polak², Andre L. M. Porto³, Iracema H. Schoenlein-Crusius⁴ and Joao V. Comasseto⁵
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¹ Laboratorio de Quimica Fina e Biocatalise - Instituto de Quimica, Universidade de Sao Paulo, Av. Prof. Lineu Prestes, no 748, CEP 05508-900, Sao Paulo, SP, Brazil. ² Laboratorio de Quimica Fina e Biocatalise - Instituto de Quimica, Universidade de Sao Paulo, Av. Prof. Lineu Prestes, no 748, CEP 05508-900, Sao Paulo, SP, Brazil. ³ Laboratorio de Quimica Fina e Biocatalise - Instituto de Quimica, Universidade de Sao Paulo, Av. Prof. Lineu Prestes, no 748, CEP 05508-900, Sao Paulo, SP, Brazil. ⁴ Laboratorio de Quimica Fina e Biocatalise - Instituto de Quimica, Universidade de Sao Paulo, Av. Prof. Lineu Prestes, no 748, CEP 05508-900, Sao Paulo, SP, Brazil. ⁵ Laboratorio de Quimica Fina e Biocatalise - Instituto de Quimica, Universidade de Sao Paulo, Av. Prof. Lineu Prestes, no 748, CEP 05508-900, Sao Paulo, SP, Brazil.
Source: Letters in Organic Chemistry, Volume 3, Issue 8, Aug 2006, p. 613 - 618
DOI: https://doi.org/10.2174/157017806778559509
- Available online: 01 Aug 2006

Abstract

The enantioselective bioreduction of alpha-substituted-acetophenones 1,2 was carried out with cells of fungi to give the corresponding chiral alcohols in good yield and high enantioselectivity (up to 99%). The chiral alcohols 3 and 4 obtained by this methodology are important intermediates for the asymmetric syntheses of chiral drugs. The enantioselectivity presented by several fungal strains was anti-Prelog.

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2006-08-01

2025-10-03

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Article Type: Research Article

Keyword(s): Bioreduction; chiral alcohol; fungus; hydrolysis; ketone

Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-Phenylethanols

Abstract

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