Sintese biocatalitica de beta -amino- alfa -hidroxiacidos : aplicações na sintese de heterociclos quirais / Sintese biocatalitica de B-amino-a-hidroxiacidos : aplicações na sintese de heterociclos quirais

AUTOR(ES)
DATA DE PUBLICAÇÃO

2005

RESUMO

Homochiral b-amino-a-hydroxy acids are key components of many compounds with important pharmacological activities. In this work, we have performed a synthetic study in order to develop a general methodology to synthesize these compounds. We have specially investigated the bioreductions of a-ketoesters (with an a-carbonyl R group that could lead to nitrogened substituents) using different microorganisms in both a free and Ímmobilized forms. We developed a new methodology to for b-halo-a-ketoesters reduction so that a phenylnorstatine derivative could be obtained with good global yield (54%) and excellent ee (96%). The proposed protocol was efficient used in the synthesis of others b-amino-a-hydroxyesters. We have synthesized different chiral heterocycles, such as oxazoline and epoxide. which were obtained as intennediates in b-amino-a-hydroxy acids synthesis. In parallel, we developed a bioreduction process protocol mediated by Saccharomyces cerevisiae in a continuously operated bioreactor. Good stability, high yield and high ee were obtained. We also used MIMS (Membrane Introduction Mass Spectrometry) technique to monitor bioreduction reactions. MIMS is a technique suitable for rapid on fine and real time monitoring of bioreduction reactions.

ASSUNTO(S)

beta-amino-hidroxi-acidos alginato de calcio saccharomyces cerevisiae biocatalise

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