Synthesis of the C1-phosphonate analog of UDP-GlcNAc.
We describe the first synthesis of the C1-phosphonate analog of UDP-GlcNAc, based on a new preparation of the corresponding glycosyl phosphonate. This C-glycosyl analog is shown to be a very weak inhibitor (Ki>10 mM) of fungal chitin synthase, indicating that at least in this case the replacement of the anomeric oxygen with a methylene group is not an innocent substitution.
Chang
Robert
R
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0358, USA.
Vo
Thanh-Trang
TT
Finney
Nathaniel S
NS
D002687:Chitin Synthase / Q000037:antagonists & inhibitors / Q000378:metabolism; D006027:Glycosides / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D014537:Uridine Diphosphate N-Acetylglucosamine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D006027:Glycosides; D063065:Organophosphonates; D014537:Uridine Diphosphate N-Acetylglucosamine; D002687:Chitin Synthase