Media type: E-Article Title: Stereoselective Chemoenzymatic Synthesis of UDP‐1,2‐cis‐furanoses from α,β‐Furanosyl 1‐Phosphates Contributor: Peltier, Pauline; Guégan, Jean‐Paul; Daniellou, Richard; Nugier‐Chauvin, Caroline; Ferrières, Vincent Published: Wiley, 2008 Published in: European Journal of Organic Chemistry, 2008 (2008) 35, Seite 5988-5994 Language: English DOI: 10.1002/ejoc.200800742 ISSN: 1099-0690; 1434-193X Keywords: Organic Chemistry ; Physical and Theoretical Chemistry Origination: Footnote: Description: <jats:title>Abstract</jats:title><jats:p>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 nucleotide‐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‐β‐<jats:sc>L</jats:sc>‐arabinofuranose, UDP‐α‐<jats:sc>D</jats:sc>‐fucofuranose and UDP‐α‐<jats:sc>D</jats:sc>‐6F‐galactofuranose from starting mixtures of sugar‐phosphates.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</jats:p>