Chemical synthesis of UDP-4-O-methyl-GlcNAc, a potential chain terminator of chitin synthesis.
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.
Chang
Robert
R
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0358, USA.
Moquist
Philip
P
Finney
Nathaniel S
NS
D002240:Carbohydrate Sequence; D002686:Chitin / Q000096:biosynthesis*; D002687:Chitin Synthase / Q000378:metabolism; D008969:Molecular Sequence Data; D014539:Uridine Diphosphate Sugars / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
C494568:UDP-4-O-methyl-N-acetylglucosamine; D014539:Uridine Diphosphate Sugars; D002686:Chitin; D002687:Chitin Synthase