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Stereoselective Chemoenzymatic Synthesis of UDP‐1,2‐ cis ‐furanoses from α,β‐Furanosyl 1‐Phosphates
Author(s) -
Peltier Pauline,
Guégan JeanPaul,
Daniellou Richard,
NugierChauvin Caroline,
Ferrières Vincent
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800742
Subject(s) - glycoconjugate , stereoselectivity , chemistry , biosynthesis , enzyme , nucleotide , substrate (aquarium) , sugar , stereochemistry , biocatalysis , combinatorial chemistry , biochemistry , catalysis , gene , biology , reaction mechanism , ecology
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‐ L ‐arabinofuranose, UDP‐α‐ D ‐fucofuranose and UDP‐α‐ D ‐6F‐galactofuranose from starting mixtures of sugar‐phosphates.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)