Glycofuranosides and other furanosic derivatives. Simple procedures for the synthesis of glycobiological tools

MARINO C.

Villa Gral. Belgrano, Córdoba

Simposio; 2° Argentinean Glycobiology Symposium (GlycoAr 2016); 2016

Sociedad Argentina de GLicobiología

Most sugars lead by conventional methods to pyranosic derivatives, which are thermodynamically more stable. In conditions under other monosaccharides lead mainly to pyranosic products, large proportions of D-galactofuranose (D-Galf) derivatives can be obtained from galactose. The interest in D-Galf containing molecules arises from the fact that D-Galf is present in glycoconjugates of microorganisms, many of them being pathogenic, but is absent in higher eukaryotes. Glycoconjugates, synthetic oligosaccharides and glycomimetics containing D-Galf units are valuable tools for elucidating the mechanisms of action of the enzymes related to the glycobiology of this sugar and for the identification and design of potantial therapeutic agents. The synthesis of these compounds requires the efficient preparation of derivatives of D-Gal in the furanosic configuration, free from the pyranosic forms, as precursors of D-Galf units in the target molecules. Furthermore, efficient glycosylation methodologies and the consequent availability of galactofuranosyl donors, as well as conveniently substituted derivatives as glycosyl acceptors are required. Some of the contributions made to these different aspects of the synthesis of D-Galf containing molecules, as well as of other furanosic sugars will be described.