Journal
CARBOHYDRATE RESEARCH
Volume 341, Issue 12, Pages 1998-2004Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2006.05.008
Keywords
UDP-GlcNAc; glycosyl phosphonate; chitin synthase; glycosyl transferase inhibition
Funding
- NIGMS NIH HHS [GM60875, GM61894, GM62116] Funding Source: Medline
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We describe the first synthesis of the Cl-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 (K-i > 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. (c) 2006 Elsevier Ltd. All rights reserved.
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