Diastereoselective synthesis of novel iminosugar-containing UDP-Galf mimics: potential inhibitors of UDP-Gal mutase and UDP-Galf transferases |
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Authors: | Liautard Virginie Christina Alphert E Desvergnes Valérie Martin Olivier R |
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Institution: | Institut de Chimie Organique et Analytique, CNRS and Université d'Orléans, BP 6759, 45067 Orléans, France. |
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Abstract: | Tetra-O-benzyl-D-glucofuranose was converted into uridine diphosphono-beta-Galf mimics based on an iminosugar skeleton linked to UMP by a 2-hydroxypropyl tether. The synthesis is based on the highly regio- and stereoselective cycloaddition of an original uridin-5'-yl allylphosphonate with a 1,4-dideoxy-1,4-iminogalactitol-derived cyclic nitrone, followed by the reductive elaboration of the cycloaddition product. The resulting iminogalactose-UMP conjugates are novel sugar nucleotide mimics which could be useful as inhibitors of UDP-Gal mutase and UDP-Galf transferases. |
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