Synthesis of alpha-D-Galactofuranosyl Phosphate

MARINO C.; ATTORRESI, CECILIA; MUCHNIK DE LEDERKREMER

Carbohydrate Chemistry: Proven synthetic Methods.

CRC Press

Año: 2013; p. 217 - 224

Galactofuranosyl units (Galf), mainly in the b-configuration, are constituents of infectious microorganisms, such as the Mycobacteria,1 trypanosomatids like Trypanosoma cruzi and Leishmania, and fungi like Aspergillus fumigatus. The metabolic pathways involved in the biosynthesis of the microbial glycoconjugates containing Galf are attractive targets for the development of therapeutic agents, because Galf is absent in mammalian cells. The enzymes involved in the biosynthesis of Galf-containing molecules are the UDP-galactopyranosyl mutase (UMG), which catalyzes the interconversion of UDP-Galp into UDP-Galf, the natural donor of Galf units, and the galactofuranosyltransferases, which are responsible for the incorporation of the sugar into the glycoconjugates. The galactofuranosyl transferases (GlfTs), working in vivo after UGM for the introduction of Galf in glycans were less studied than the mutases, probably due to the difficulties in obtaining the activated donor UDP-Galf. Several chemical syntheses of the Galf nucleotide have been reported. Recently, an effective chemoenzymatic procedure for the preparation of UDP-Galf was described in detail.