Novel and efficient chemoenzymatic synthesis of D-glucose 6-phosphate and molecular modeling studies on the selective biocatalysis

Article abstract of DOI:10.1002/ejoc.200700017

A concise chemoenzymatic synthesis of glucose 6-phosphate is described. Candida rugosa lipase was found to be an efficient catalyst for both regio- and stereoselective deacetylation of the primary hydroxy group in the peracetylated D-glucose. In addition, we report an improved synthesis of 1,2,3,4,6-penta-O- acetyl-α-D-glucopyranose providing a large-scale procedure for the acetylation of α-D-glucose without isomerization at the anomeric center. The high overall yield and the easy scalability makes this chemoenzymatic strategy attractive for industrial application. Furthermore, molecular modeling of phosphonate transition-state analog for the enzymatic hydrolysis step supports the substrate selectivity observed with Candida rugosa lipase. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.