The preparation of deoxy derivatives of mannose-1-phosphate and their substrate specificity towards recombinant GDP-mannose pyrophosphorylase from Salmonella enterica, group B

Abstract

2-Deoxy-α -d-glucose-1-phosphate, 3-deoxy-α -d- arabino-hexose-1-phosphate, 4-deoxy-α -d- lyxo-hexose-1-phosphate, and α -d-lyxose-1-phosphate were synthesised chemically, and evaluated as substrates for a recombinant G DP-mannose pyrophosphorylase ( Salmonella enterica, group B, cloned in Escherichia coli). The deoxy derivatives were all substrates for the enzyme, with slightly reduced V max values but significantly higher K m values than those recorded for the native substrate, mannose-1-phosphate. The pyrophosphorylase was used for the synthesis of GDP-mannose analogues GDP-2-deoxy-glucose and GDP-lyxose on a milligram scale.