Bioreduction of beta-carboline imines to amines employing Saccharomyces bayanus


Autoria(s): ESPINOZA-MORAGA, Marlene; PETTA, Tania; VASQUEZ-VASQUEZ, Marco; LAURIE, V. Felipe; MORAES, Luis A. B.; SANTOS, Leonardo Silva
Contribuinte(s)

UNIVERSIDADE DE SÃO PAULO

Data(s)

19/10/2012

19/10/2012

2010

Resumo

beta-Carboline imine reductions mediated by Saccharomyces bayanus have been described achieving moderate to good enantiomeric excesses of the amine products. The enantiomeric excesses of the bioreduction showed a dependence on the imine substituents. Compounds presenting C(1)-C(11) aliphatic substituent groups afforded amines with an (S)-configuration, whereas C(15) and higher aliphatic, and aromatic substituted B-carboline imines achieved inversion of the configuration in the final (R)-2 amine products. Based on this data, a model for the Saccharomyces reduction is proposed. (C) 2010 Elsevier Ltd. All rights reserved.

FONDECYT[1085308]

Programa de Doctorado en Productos Bioactivos-UTalca

Identificador

TETRAHEDRON-ASYMMETRY, v.21, n.16, p.1988-1992, 2010

0957-4166

http://producao.usp.br/handle/BDPI/20818

10.1016/j.tetasy.2010.06.036

http://dx.doi.org/10.1016/j.tetasy.2010.06.036

Idioma(s)

eng

Publicador

PERGAMON-ELSEVIER SCIENCE LTD

Relação

Tetrahedron-asymmetry

Direitos

restrictedAccess

Copyright PERGAMON-ELSEVIER SCIENCE LTD

Palavras-Chave #ENANTIOSELECTIVE TOTAL-SYNTHESIS #PICTET-SPENGLER REACTIONS #PHARMACOLOGICAL PROPERTIES #ASYMMETRIC REDUCTION #CEREVISIAE #STRAINS #TRYPTAMINES #CATABOLISM #WINES #CHAIN #Chemistry, Inorganic & Nuclear #Chemistry, Organic #Chemistry, Physical
Tipo

article

original article

publishedVersion