A whole-cell based biocatalysis method was successfully applied in highly-regioselective transesterification of glucose with vinyl propionate. The whole-cell biocatalyst prepared from the P. stutzeri strain showed higher regioselectivity than 99% toward the 6-OH group of the sugar. The lyophilized cells also showed an evident solvent dependence in the reaction. Among the tested solvents except for acetonitrile-pyridine and tetrahydrofuran-pyridine, the substrate conversion clearly increased with increasing hydrophobicity of the organic solvents used. In a binary mixture of a lipophilic solvent (isooctane) and hydrophilic one (pyridine), the initial rate and conversion of the reaction were higher than 29 mmol/L and 97%, respectively, under optimum conditions. A preparative-scale production of 6-O-glucose ester without any significant loss of conversion and initial rate than the analytical scale further demonstrated that whole-cell of P. stutzeri was an efficient and highly-regioselective alternative to enzymes for �green� synthesis of glucose monoesters with high purity.

Efficient and highly-regioselectivesynthesis of 6-O-propionyl-D-glucose by using whole-cell biocatalysts

248th National Meeting (2014)

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