title: Synthesis of a novel UDP-carbasugar as UDP-galactopyranose mutase inhibitor.
abstract: The multistep synthesis of a novel UDP-C-cyclohexene, designed as a high energy intermediate analogue of the UDP-galactopyranose mutase (UGM) catalyzed isomerization reaction, is reported. The synthesis of the central carbasugar involved the preparation of a galactitol derivative bearing two olefins necessary for the construction of the cyclohexene ring by a ring-closing metathesis as a key step. Further successive phosphonylation, deprotection, and UMP coupling provided the target molecule. The final molecule was assayed against UGM and compared with UDP-C-Galf, the C-glycosidic UGM substrate analogue.
authors.affiliation: University of Namur , Département de Chimie, Laboratoire de Chimie Bio-Organique, rue de Bruxelles 61, B-5000 Namur, Belgium.
authors.forename: Sandy
authors.initials: S
authors.lastname: El Bkassiny
authors.forename: Inès
authors.initials: I
authors.lastname: N'Go
authors.forename: Charlotte M
authors.initials: CM
authors.lastname: Sevrain
authors.forename: Abdellatif
authors.initials: A
authors.lastname: Tikad
authors.forename: Stéphane P
authors.initials: SP
authors.lastname: Vincent
mesh_terms: D054329:Carbasugars / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D003510:Cyclohexanes / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D019751:Intramolecular Transferases / Q000037:antagonists & inhibitors* / Q000737:chemistry; D007536:Isomerism; D015394:Molecular Structure; D014530:Uridine Diphosphate / Q000737:chemistry*
chemical_list: D054329:Carbasugars; D003510:Cyclohexanes; D006027:Glycosides; D014530:Uridine Diphosphate; D019751:Intramolecular Transferases; C098051:UDP-galactopyranose mutase