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>10mM) of fungal chitin synthase, indicating that at least in this case the replacement...

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Veröffentlicht in:	Carbohydrate research 2006-09, Vol.341 (12), p.1998-2004
Hauptverfasser:	Chang, Robert, Vo, Thanh-Trang, Finney, Nathaniel S.
Format:	Artikel
Sprache:	eng
Schlagworte:	Chitin synthase Chitin Synthase - antagonists & inhibitors Chitin Synthase - metabolism Glycosides - chemistry Glycosyl phosphonate Glycosyl transferase inhibition Models, Chemical Molecular Structure Organophosphonates - chemistry UDP-GlcNAc Uridine Diphosphate N-Acetylglucosamine - chemical synthesis Uridine Diphosphate N-Acetylglucosamine - chemistry Uridine Diphosphate N-Acetylglucosamine - pharmacology
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Beschreibung
Zusammenfassung:	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>10mM) 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.
ISSN:	0008-6215 1873-426X
DOI:	10.1016/j.carres.2006.05.008