Synthesis of two isosterics phosphono analogues of D-Galactofuranosyl phosphate

JOSÉ KOVENSKY, ALICIA FERNÁNDEZ CIRELLI AND PIERRE SINAY

Carbohydrate Letters

Harwood Academic

Lugar: Amsterdam; Año: 1999 vol. 3 p. 271 - 276

1073-5070

Abstract Two C-analogues of galactofuranosyl phosphate, with µ and b anomeric configuration, have been selectively synthesized in sizeable amounts. D-Galactofuranose is know for many years as a typical monosaccaharide componenet of varius plysaccharides and glycoconjugates from infectious bacteria, protozoa and fungi. UDP-Galf has been shown  to be the substrate for putative galactofuranosyl transferases wich probably should transfer D-Galf units onto growing oligosaccaharide chains. This novel Leloir sugar nucleotide is formed from the well know UDP-Galp by a key rearrangement mediated by the enzyme UDP-galactopyranose mutase. Since D-Galf residues are not present in humans, inhibitors of the enzymes involved either in their formation (mutase) or their transfer onto carbohydrate chains (tranferase) become important drug targets. Since D-Galf residues are not present in humans, inhibitors of the enzymes involved either in their formation (mutase) or their transfer onto carbohydrate chains (tranferase) become important drug targets. Since D-Galf residues are not present in humans, inhibitors of the enzymes involved either in their formation (mutase) or their transfer onto carbohydrate chains (tranferase) become important drug targets.