Chemoenzymatic synthesis of stable isotope labeled UDP-N-[2H]-acetyl-glucosamine and [2H]-acetyl-chitooligosaccharides

• Published in: Glycoconjugate journal Vol. 23; no. 9; pp. 687 - 692
• Main Authors: Becker, Hubert F, Thellend, Annie, Piffeteau, Annie, Vidal-Cros, Anne
• Format: Journal Article
• Language: English
• Published: United States Springer Nature B.V 01.12.2006; Springer Verlag
• Subjects: Acetylation; Carbohydrate Sequence; Chemical Sciences; Chitin - metabolism; Chitin Synthase - analysis; Chitin Synthase - metabolism; Chromatography, Thin Layer; Deuterium - metabolism; Mass spectrometry; Molecular Structure; Oligosaccharides - metabolism; Organic chemistry; Spectrometry, Mass, Electrospray Ionization; Uridine Diphosphate N-Acetylglucosamine - chemical synthesis; Uridine Diphosphate N-Acetylglucosamine - chemistry
• ISSN: 0282-0080; 1573-4986
• DOI: 10.1007/s10719-006-9018-8

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.