Resolução enzimática de álcoois racêmicos com lipase de Candida antarctica e redução de cetonas com fungos de origem marinha / Resolution enzymatic of alcohols secondary with lipase of Candida antartica and reduction of ketones with fungi of marine origin

AUTOR(ES)
DATA DE PUBLICAÇÃO

2008

RESUMO

This work carried out the enzymatic reactions of alcohols by using a lipase from immobilized Candida Antarctica (NOVOZYME 435). The alcohols used were: (RS)-1- (4-methoxyphenyl) ethanol (1a), (RS)-4-methyl-2-pentanol (3a), (RS)-2-methyl-3- hexanol (4a), (RS)-5-methyl-2-hexanol (5a), (RS)-2-octanol (6a), (RS)-3-heptanol (7a), (RS)-6-methyl-5-hepten-2-ol (8a) and (RS)-1-octen-3-ol (9a). All the alcohols were catalyzed by lipase, except for the alcohol 4a. In this enzymatic resolutions the enantiomeric excesses of alcohols and acetates were more than 98% and total conversions (50%) for enantiomers of the acetates: (R)-1-acetate-4-methoxyphenyl (1b), (R)-2-acetate-4-methyl-pentane (3b), (R)-2-acetate-5-methyl-hexane (5b), (R)-2-acetateoctane (6b), (R)-3-acetate-heptane (7b), (R)-2-acetate-6-methyl-5-hepteno (8b) and (S)- 3-acetate-1-octene (9b). In addition it was studied the biocatalytic reduction of ketones with marine-derived fungi. The ketones used were the 4-metoxyacetophenone (1), 1- phenyl-etanone (2), 4-methyl-2-pentanone (3), 2-octanone (6) and 6-methyl-5-hetpen-2- one (8). The marine-derived fungi used as biocatalysts were Bionectria sp Ce5, Aspergillus sydowii Ce15 and Aspergillus sydowii Ce19. The 4-metoxyacetophenone (1) was reduced by Bionectria sp Ce5 by Aspergillus sydowii Ce15 and Aspergillus sydowii Ce19 in high enantiomeric excess (98% e.e.) and good yield, i.g., 65%. The 2- octanone (6) and 6-methyl-5-hepten-2-one (8) were reduced by A. sydowii Ce15 in the (R)-alcohols 6a and 8a in high enantiomeric purities, >98% e.e. However the 1-phenyletanone (2) was reduced only by the fungus Bionectria sp Ce5 with enantiomeric excess of 50% and yield of 25%. The 4-methyl-2-pentanone (3) was not reduced by the microorganisms studied.

ASSUNTO(S)

redução biocatalysts reduction fungos biocatálise fungi

ACESSO AO ARTIGO

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