Synthesis of D-galactofuranose-containing molecules: design of galactofuranosyl acceptors

Abstract

D-Galactofuranose (D-Galf) is present in glycoconjugates of several pathogenic microorganisms but is absent in mammals, so it is a good target for the development of chemotherapeutic agents for the treatment of microbial infections. This fact has increased interest in the synthesis of D-Galf-containing molecules for corresponding glycobiological studies. The synthesis of oligosaccharides, glycoconjugates, and mimetics of D-Galf requires specific methods for the preparation of galactose derivatives in the furanosic configuration, the synthesis of appropriate acceptors, and efficient glycosylation methods for the construction of α- and β-D-Galf linkages. This review summarizes the different strategies developed for the preparation of partially protected derivatives of D-Galf, suitable as acceptors for the construction of (1→2), (1→3), (1→5), and (1→6) link- ages, and describes recent applications.

Keywords: carbohydrates; galactofuranosides; galactofuranosyl acceptors; glycosylation; organic synthesis.