Synthesis of a novel UDP-carbasugar as UDP-galactopyranose mutase inhibitor.

Sandy El Bkassiny, Inès N'Go, Charlotte M Sevrain, Abdellatif Tikad, Stéphane P Vincent

Organic letters 2014 May 2

filter terms:

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.

Citation

Sandy El Bkassiny, Inès N'Go, Charlotte M Sevrain, Abdellatif Tikad, Stéphane P Vincent. Synthesis of a novel UDP-carbasugar as UDP-galactopyranose mutase inhibitor. Organic letters. 2014 May 2;16(9):2462-5