Highly enantioselective deracemization of 1-phenyl-1,2-ethanediol and its derivatives by stereoinversion using Candida albicans in a one-pot process

Author(s)

Cazetta, Tarcila ^[1] ; Moran, Paulo J. S. ^[1] ; Rodrigues, J. Augusto R. ^[1]

Affiliation

^[1] Univ Estadual Campinas, Inst Chem, BR-13084971 Campinas, SP - Brazil

• Document type: Review article
• Source: JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC; v. 109, p. 178-183, NOV 2014.
• Web of Science Citations: 7

Abstract

A very simple methodology was developed to transform racemic 1-(4-substitutedphenyl)-1,2-ethanediols using resting cells of Candida albicans CCT 0776 through a one-pot two-step process in which the (R)-stereoisomer was completely oxidized to the corresponding substituted-alpha-hydroxyacetophenones, which were completely reduced to produce (S)-1-(4-substitutedphenyl)-1,2-ethanediols in good isolated yield (60-85%) and with high enantiomeric excess (99% ee). The overall process corresponded to an enantioselective deracemization by stereoinversion of the (R)-enantiomer. The process was not achieved for other similar 1,2-diols using the same reaction conditions, which indicates a structural restriction of substrates by the active pocket of the enzymes of C. albicans involved in the stereoinversion process. (C) 2014 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 14/00108-9 - Application of biocatalysis in organic synthesis using whole cells of microorganisms
• Grantee: José Augusto Rosário Rodrigues
• Support Opportunities: Regular Research Grants