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

Autor(es)

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

Afiliação do(s) autor(es)

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

• Tipo de documento: Artigo de Revisão
• Fonte: JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC; v. 109, p. 178-183, NOV 2014.
• Citações Web of Science: 7

Resumo

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)

• Processo FAPESP: 10/51711-6 - Estudo da redução de metileno-b-cetoesteres por microrganismos
• Beneficiário: Tarcila Cazetta
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 14/00108-9 - Aplicação de biocatálise em síntese orgânica empregando células íntegras de microrganismos
• Beneficiário: José Augusto Rosário Rodrigues
• Modalidade de apoio: Auxílio à Pesquisa - Regular