title: Chemoenzymatic synthesis of stable isotope labeled UDP-N-[2H]-acetyl-glucosamine and [2H]-acetyl-chitooligosaccharides.
abstract: Labeled UDP-GlcNAc and chitooligosaccharides should be powerful tools for studies of N-acetylglucosaminyltransferase such as chitin synthases. We describe here a rapid, inexpensive and a common strategie for the chemoenzymatic synthesis of uridine 5'-diphospho-N-[(2)H]-acetyl-glucosamine and the chemical preparation of N-[(2)H]-acetyl chitooligosaccharides (from 2 to 5 mers). Deuterated UDP-GlcNAc analogue was tested as chitin synthase substrate and it exhibited an incorporation level in chitin as the natural substrate. Deuterium labeling of carbohydrates present different advantages: it is a stable isotope and allows glycosyltransferase mechanism studies by a mass spectrometry approach.
authors.affiliation: Synthèse, Structure et Fonction de Molécules Bioactives UMR7613, Université Pierre et Marie Curie, Tour 44-45, 3ème étage, 4 place Jussieu, 75252, Paris, France. hbecker@moka.ccr.jussieu.fr
authors.forename: Hubert F
authors.initials: HF
authors.lastname: Becker
authors.forename: Annie
authors.initials: A
authors.lastname: Thellend
authors.forename: Annie
authors.initials: A
authors.lastname: Piffeteau
authors.forename: Anne
authors.initials: A
authors.lastname: Vidal-Cros
mesh_terms: D000107:Acetylation; D002240:Carbohydrate Sequence; D002686:Chitin / Q000378:metabolism*; D002687:Chitin Synthase / Q000032:analysis / Q000378:metabolism; D002855:Chromatography, Thin Layer; D003903:Deuterium / Q000378:metabolism*; D015394:Molecular Structure; D009844:Oligosaccharides / Q000378:metabolism*; D021241:Spectrometry, Mass, Electrospray Ionization; D014537:Uridine Diphosphate N-Acetylglucosamine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009844:Oligosaccharides; D002686:Chitin; D014537:Uridine Diphosphate N-Acetylglucosamine; D003903:Deuterium; D002687:Chitin Synthase