Chemoenzymatic synthesis of stable isotope labeled UDP-N-[2H]-acetyl-glucosamine and [2H]-acetyl-chitooligosaccharides.
Identifieur interne : 000196 ( France/Analysis ); précédent : 000195; suivant : 000197Chemoenzymatic synthesis of stable isotope labeled UDP-N-[2H]-acetyl-glucosamine and [2H]-acetyl-chitooligosaccharides.
Auteurs : Hubert F. Becker [France] ; Annie Thellend ; Annie Piffeteau ; Anne Vidal-CrosSource :
- Glycoconjugate journal [ 0282-0080 ] ; 2006.
Descripteurs français
- KwdFr :
- Acétylation, Chitine (métabolisme), Chitine synthase (analyse), Chitine synthase (métabolisme), Chromatographie sur couche mince, Deutérium (métabolisme), Oligosaccharides (métabolisme), Spectrométrie de masse ESI, Structure moléculaire, Séquence glucidique, Uridine diphosphate N-acétylglucosamine (), Uridine diphosphate N-acétylglucosamine (synthèse chimique).
- MESH :
- analyse : Chitine synthase.
- métabolisme : Chitine, Chitine synthase, Deutérium, Oligosaccharides.
- synthèse chimique : Uridine diphosphate N-acétylglucosamine.
- Acétylation, Chromatographie sur couche mince, Spectrométrie de masse ESI, Structure moléculaire, Séquence glucidique, Uridine diphosphate N-acétylglucosamine.
English descriptors
- KwdEn :
- Acetylation, Carbohydrate Sequence, Chitin (metabolism), Chitin Synthase (analysis), Chitin Synthase (metabolism), Chromatography, Thin Layer, Deuterium (metabolism), Molecular Structure, Oligosaccharides (metabolism), Spectrometry, Mass, Electrospray Ionization, Uridine Diphosphate N-Acetylglucosamine (chemical synthesis), Uridine Diphosphate N-Acetylglucosamine (chemistry).
- MESH :
- chemical , analysis : Chitin Synthase.
- chemical , chemical synthesis : Uridine Diphosphate N-Acetylglucosamine.
- chemical , chemistry : Uridine Diphosphate N-Acetylglucosamine.
- chemical , metabolism : Chitin, Chitin Synthase, Deuterium, Oligosaccharides.
- Acetylation, Carbohydrate Sequence, Chromatography, Thin Layer, Molecular Structure, Spectrometry, Mass, Electrospray Ionization.
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.
DOI: 10.1007/s10719-006-9018-8
PubMed: 17123165
Affiliations:
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pubmed:17123165Le document en format XML
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