1.
Org Lett
; 23(5): 1638-1642, 2021 03 05.
Article
in English
| MEDLINE
| ID: mdl-33620227
ABSTRACT
The multistep synthesis of a novel ADP-7-azido-7-deoxy-l-glycero-ß-d-manno-heptopyranoside 2a and several analogues as heptosyltransferase ligands is described. The synthesis of the key intermediate heptoside-1-ß-phosphate 3a involved a ß-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).