Synthesis of fluorescently labeled UDP-GlcNAc analogues and their evaluation as chitin synthase substrates.
[structure: see text] Chitin synthase (CS) polymerizes UDP-GlcNAc to form chitin (poly-beta(1,4)-GlcNAc), a key component of fungal cell wall biosynthesis. Little is known about the substrate specificity of chitin synthase or the scope of substrate modification the enzyme will tolerate. Following a previous report suggesting that 6-O-dansyl GlcNAc is biosynthetically incorporated into chitin, we became interested in developing an assay for CS activity based on incorporation of a fluorescent substrate. We describe the synthesis of two fluorescent UDP-GlcNAc analogues and their evaluation as chitin synthase substrates.
Yeager
Adam R
AR
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Dr., La Jolla, California 92093, USA.
Finney
Nathaniel S
NS
D002686:Chitin / Q000096:biosynthesis / Q000737:chemistry / Q000378:metabolism; D002687:Chitin Synthase / Q000378:metabolism*; D005456:Fluorescent Dyes / Q000737:chemistry; D015394:Molecular Structure; D013379:Substrate Specificity; D014537:Uridine Diphosphate N-Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*
D005456:Fluorescent Dyes; D002686:Chitin; D014537:Uridine Diphosphate N-Acetylglucosamine; D002687:Chitin Synthase