The First Chemical Synthesis of UDP[6-3H]-alpha-D-galactofuranose

MARIÑO, KARINA; MARINO, CARLA; LIMA, CARLOS; BALDONI, LUCIANA; LEDERKREMER, ROSA M. DE

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

WILEY-V C H VERLAG GMBH

Año: 2005 vol. 2005 p. 2958 - 2964

1434-193X

Galactofuranose metabolism is a good target for the develop- ment of novel chemotherapeutic agents for the treatment of some microbial infections. This is a valid objective because galactofuranose is absent in mammals. Two enzymes are in- volved in the biosynthesis of molecules containing galactofu- ranose: a mutase, which catalyzes the interconversion of UDP-Galp and UDP-Galf, and D-galactofuranosyltransfer- ases. The mechanism of action of the mutase and its inhibi- tion is currently being investigated, whereas studies on the galactofuranosyltransferases have been hampered by the lack of a labeled galactofuranose nucleotide. In the present work we describe the chemical synthesis of UDP-α-D-[6- 3H]Galf and we prove its effectiveness for incorporation of radioactive galactofuranose into a natural acceptor. This is the first report on the chemical synthesis of a labeled donor of galactofuranose with the potential for studying the galac- tofuranosyltransferases independently from the UDP-Galp mutase.