Chiral Pharmaceutical Intermediaries Obtained by Reduction of 2-Halo-1-(4-substituted phenyl)-ethanones Mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182

Abstract

Enantioselective reductions of p-R1-C6H4C(O)CH2R2 (R1 = Cl, Br, CH3, OCH3, NO2 and R2 = Br, Cl) mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182 afforded the corresponding halohydrins with complementary R and S configurations, respectively, in excellent yield and enantiomeric excesses. The obtained (R)- or (S)-halohydrins are important building blocks in chemical and pharmaceutical industries.

Lyophilized Rhodotorula yeast as all-in-one redox biocatalyst: Access to enantiopure building blocks by simple chemoenzymatic one-pot procedures

“…1). The importance of having stereo-complementary whole cell catalysts that provide both enantiomers of the halohydrins has already been standed out by other authors, for example, R. ruber and Pseudomona flourescens to prepare the Prelog and anti-Prelog isomers, respectively [8] and Rhodotorula glutinis and Geotrichum candidum in a more recent report [27].…”

PRODUÇÃO DE COMPOSTOS a-HIDROXIFOSFONATOS OPTICAMENTE ATIVOS UTILIZANDO CÉLULAS ÍNTEGRAS DE MICRORGANISMOS

“…A biocatálise é um dos principais métodos utilizados em síntese enantiosseletiva devido ao uso de enzimas e células íntegras, e estas possuem alta químio-, regio-e estereosseletividade (CAZETTA et al, 2014;FARDELONE et al, 2011;RODRIGUES et al, 2004). Normalmente as condições de reações são brandas, pois utilizam baixas temperaturas ou ambiente e pressão atmosférica, e compostos "não naturais" podem ser aceitos como substratos.…”

Highly Enantioselective Production of (R)-Halohydrins with Whole Cells of Rhodotorula rubra KCh 82 Culture

“…This may be achieved either by chemical methods [ 9 , 10 , 11 ], or by biotechnological ones. The effective enantioselectivity of the desired product was achieved either by using whole cells of biocatalysts [ 12 , 13 , 14 , 15 , 16 ] or with the help of isolated enzymes, such as dehydrogenases [ 1 , 17 , 18 ] and lipases [ 19 ]. Although in the majority of the reported studies, the halohydrins were obtained with high substrate conversions and high enantiomeric excesses, there is always a risk of side products due to reductive dehalogenation (leading to respective 1-phenylehtan-1,2-diols) and substitution (2-hydroxyacetophenone and 1-phenylehtan-1,2-diol) [ 20 , 21 ].…”