Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 35, Pages 5988-5994Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800742
Keywords
Carbohydrates; Nucleotides; Glycoconjugates; Enzyme catalysis
Categories
Funding
- Region Bretagne
- Rennes Metropole
- Agence Nationale de la Recherche [ANR JCJC06_140075]
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The biosynthesis of furanosyl-containing glycoconjugates is poorly described, mainly due to the lack of UDP-furanoses. Here we present our effort to synthesize rare nucleoticle-sugars with the aid of a multiple-enzyme system, notably including galactose-1-phosphate uridylyltransferase. Firstly, STD-NMR techniques were used to probe the broad substrate specificity of this particular enzyme. The chemical synthesis of the needed furanosyl 1-phosphate starting materials was then performed with unprotected thioimidoyl donors. This led to the first stereoselective chemoenzymatic syntheses of UDP-beta-L-arabinofuranose, UDP-alpha-D-fucofuranose and UDP-alpha-D-6F-galactofuranose from starting mixtures of sugar-phosphates. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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