Synthesis of novel donor mimetics of UDP-Gal, UDP-GlcNAc, and UDP-GalNAc as potential transferase inhibitors.
For the enzymatic transfer of galactose, N-acetylglucosamine, and N-acetylgalactosamine, UDP-Gal (1), UDP-GlcNAc (2), and UDP-GalNAc (3) are employed, and UDP serves as a feedback inhibitor. In this paper the synthesis of the novel UDP-sugar analogues 4, 5, and 6 as potential transferase inhibitors is described. Compounds 4-6 feature C-glycosidic hydroxymethylene linkages between the sugar and nucleoside moieties in contrast to the anomeric oxygens in the natural derivatives 1-3.
Schäfer
A
A
Institut für Organische Chemie, Universität Hamburg, D-20146 Hamburg, Germany.
Thiem
J
J
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D014166:Transferases / Q000037:antagonists & inhibitors*; D014531:Uridine Diphosphate Galactose / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014536:Uridine Diphosphate N-Acetylgalactosamine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014537:Uridine Diphosphate N-Acetylglucosamine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D004791:Enzyme Inhibitors; D014531:Uridine Diphosphate Galactose; D014537:Uridine Diphosphate N-Acetylglucosamine; D014536:Uridine Diphosphate N-Acetylgalactosamine; D014166:Transferases