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Prikl Biokhim Mikrobiol ; 53(2): 188-95, 2017.
Artigo em Russo | MEDLINE | ID: mdl-29508979

RESUMO

A novel promising strain of actinobacteria Rhodococcus sp. 77-32 was identified. Its acetonetreated biomass the could be used as a biocatalyst for production of S-(-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl] ethanol (S-BCE), a precursor of natural α-tocols. It was established that a reaction of enantioselective hydrolysis of racemic (±)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman (BCEA) occurred in the phosphate buffer­acetone system, resulting in enrichment of the residual substrate by S-enantiomer (S-(+)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman, S-BCEA). It was shown that the hydrolysis was accompanied by stereoinversion of the formed product, R-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl] ethanol (R-BCE), into the S-BCE. The transformation conditions (acetone content, acidity, temperature, reaction duration) were optimized, providing simultaneous production of optically pure S-BCE and S-BCEA with an almost quantitative yield.


Assuntos
Cromanos/síntese química , Rhodococcus/química , Tocoferóis/síntese química , Acetona/química , Biocatálise , Biomassa , Cromanos/isolamento & purificação , Concentração de Íons de Hidrogênio , Hidrólise , Solventes/química , Estereoisomerismo , Temperatura , Tocoferóis/isolamento & purificação
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