Article

Chemical synthesis of UDP-4-O-methyl-GlcNAc, a potential chain terminator of chitin synthesis.

Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0358, USA.
Carbohydrate Research (impact factor: 2.33). 06/2004; 339(8):1531-6. DOI:10.1016/j.carres.2004.03.014
Source: PubMed

ABSTRACT Chitin synthase converts uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc) to chitin (poly-beta-(1-->4)-GlcNAc). During polymerization, elongation occurs at the 4-OH (nonreducing) terminus of the growing chitin chain. Blockage of the 4-OH via incorporation of UDP-N-acetyl-4-O-methylglucosamine (UDP-4-OMe-GlcNAc, 3) can potentially terminate chitin polymerization, and represents a novel strategy for chitin synthase inhibition. The chemical synthesis of 3 and preliminary evaluation of its possible incorporation by chitin synthase are reported herein.

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Keywords

4-OH
 
chemical synthesis
 
chitin
 
chitin polymerization
 
chitin synthase
 
Chitin synthase converts uridine diphosphoryl-N-acetylglucosamine
 
chitin synthase inhibition
 
growing chitin chain
 
herein
 
polymerization
 
possible incorporation