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

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Résumé

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).

langue originaleAnglais
titreA general strategy to synthesize ADP-7-Azido-heptose and ADP-Azido-mannoses and their heptosyltransferase binding properties
Pages1638-1642
Nombre de pages5
Volume23
Edition5
Les DOIs
Etat de la publicationPublié - 23 févr. 2021

Série de publications

NomOrganic Letters
ISSN (imprimé)1523-7060

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