A general strategy to synthesize ADP-7-Azido-heptose and ADP-Azido-mannoses and their heptosyltransferase binding properties

Research output: Contribution in Book/Catalog/Report/Conference proceedingConference contribution

Abstract

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).

Original languageEnglish
Title of host publicationA general strategy to synthesize ADP-7-Azido-heptose and ADP-Azido-mannoses and their heptosyltransferase binding properties
Pages1638-1642
Number of pages5
Volume23
Edition5
DOIs
Publication statusPublished - 23 Feb 2021

Publication series

NameOrganic Letters
ISSN (Print)1523-7060

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