Enzymatic synthesis of alkyl glucosides using Leuconostoc mesenteroides dextransucrase

Alkyl glucosides were synthesized by the reaction of Leuconostoc mesenteroides dextransucrase with sucrose and various alcohols. Alkyl alpha-d-glucosides were obtained with a yield of 30% (mol/mol) with primary alcohols, but secondary alcohols or tertiary alcohols gave yields below 5%. The optimal yield was 50% using 1-butyl alpha-d-glucoside with 0.9 M 1-butanol. The acceptor products of methanol or ethanol were confirmed as methyl alpha-d-glucopyranoside and ethyl alpha-d-glucopyranoside via MALDI-TOF MS and NMR analysis. Thus, methyl or ethyl alpha-d-glucoside constituted half the emulsification activities of Triton X-100 as commercially available surfactants.