Diastereoselective synthesis of novel iminosugar-containing UDP-Galf mimics: potential inhibitors of UDP-Gal mutase and UDP-Galf transferases.
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.
Liautard
Virginie
V
Institut de Chimie Organique et Analytique, CNRS and Université d'Orléans, BP 6759, 45067 Orléans, France.
Christina
Alphert E
AE
Desvergnes
Valérie
V
Martin
Olivier R
OR
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry; D005700:Galactosyltransferases / Q000037:antagonists & inhibitors*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D019751:Intramolecular Transferases / Q000037:antagonists & inhibitors*; D018716:Molecular Mimicry; D015394:Molecular Structure; D013237:Stereoisomerism; D014530:Uridine Diphosphate / Q000031:analogs & derivatives* / Q000737:chemistry
D004791:Enzyme Inhibitors; D050111:Imino Sugars; C104136:uridine diphosphate galactofuranose; D014530:Uridine Diphosphate; D005700:Galactosyltransferases; D019751:Intramolecular Transferases; C098051:UDP-galactopyranose mutase; D005690:Galactose