Application of the nucleotidylyltransferase E_p toward the chemoenzymatic synthesis of dTDP-desosamine analogues

Sweet transfer: The macrolide sugar β-D-desosamine (1) is a key contributor to the anti-infective properties of many macrolide antibiotics, and methods to alter this substituent may lead to macrolide variants with enhanced properties. The application of a nucleotidylyltransferase (E_p) toward the synthesis of analogues of the precursor dTDP-desosamine is demonstrated and the substrate specificity of this important class of enzyme and its integral participation in natural product 'glycorandomization' is commented on.