The multistep synthesis of a novel ADP-7-azido-7-deoxy-l-glycero-β-d-manno-heptopyranoside 2a and several analogues as heptosyltransferase ligands is described. The synthesis of the key intermediate heptoside-1-β-phosphate 3a involved a β-stereoselective phosphorylation of lactol 4 employing diallyl chlorophosphate as a phosphorylating reagent. Five deprotected nucleotide sugars were generated by this synthetic sequence and evaluated as heptosyltransferase substrates (KM, kcat).
|Title of host publication||A general strategy to synthesize ADP-7-Azido-heptose and ADP-Azido-mannoses and their heptosyltransferase binding properties|
|Number of pages||5|
|Publication status||Published - 23 Feb 2021|