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

Autor: Becker, Hubert, Thellend, Annie, Piffeteau, Annie, Vidal-Cros, Anne
Zdroj: Glycoconjugate Journal; 2006, Vol. 23 Issue 9, p687-692, 6p
Abstrakt: 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-[2H]-acetyl-glucosamine and the chemical preparation of N-[2H]-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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index