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A General Strategy to Synthesize ADP-7-Azido-heptose and ADP-Azido-mannoses and Their Heptosyltransferase Binding Properties

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journal contribution
posted on 23.02.2021, 16:05 authored by Tianlei Li, Abdellatif Tikad, Huixiao Fu, Jozafina Milicaj, Colleen D. Castro, Marine Lacritick, Weidong Pan, Erika A. Taylor, Stéphane P. Vincent
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).