Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthesis of pseudo-sugars, amino …

…, J Collins, B Sullivan, H Leisch, T Hudlicky

Index: Fabris, Fabrizio; Collins, Jonathan; Sullivan, Bradford; Leisch, Hannes; Hudlicky, Tomas Organic and Biomolecular Chemistry, 2009 , vol. 7, # 12 p. 2619 - 2627

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Citation Number: 36

Abstract

A series of benzoate esters (methyl, ethyl, n-Pr, i-Pr, n-Bu, t-Bu, allyl, and propargyl) were subjected to enzymatic dihydroxylation by E. coli JM 109 (pDTG 601) strain in a whole-cell fermentation. The cis-cyclohexadienediols were obtained in yields of∼ 1g/L except for n- propyl-and i-propyl benzoate which were found to be poor substrates. n-Butyl and t-butyl benzoates were not oxidized at all. The absolute stereochemistry for all metabolites was ...