Desenvolvimento Nos Métodos De Glicosilação: Uma Chave Para Acessar Suas Aplicações Na Síntese De Moléculas Bioativas

Abstract

DEVELOPMENT IN GLYCOSYLATION METHODS: A KEY TO ACCESS ITS APPLICATIONS IN THE SYNTHESIS OF BIOACTIVE MOLECULES. Glycosylation reaction is an important class of reactions in organic chemistry, and the development of the method contributes to the synthesis of many biologically active compounds containing various glycoside bonds. Is arguably the most important, albeit challenging, reaction in the field of carbohydrate chemistry. Examples of the products of glycosylation reactions are glycoproteins, glycolipids, glycosaminoglycans, oligosaccharides, and polysaccharides. Glycosylation types are classified according to the identity of the atom which binds the carbohydrate chain, i.e. C-linked, N-linked, O-linked or S-linked. In this short review, recent reports of the main glycosylation methods, basic mechanisms, factors influencing the stereoselectivity and their applications in the synthesis of bioactive molecules are described.

Recent Advances Related to Anomeric and Exo-anomeric Effects in Carbohydrate Chemistry

“…Fisher's important advances in glycosylation drove new research perspectives in carbohydrate chemistry in understanding glycosidic anomers and their aspects. The formation of glycosidic bonds was highlighted in glycoscience by the particularities observed for glycosidic carbon that showed stereoselective tendencies caused by stereoelectronic and thermodynamic effects [1][2][3][4]. This makes the unique carbon, defined by anomeric the first stereogenic center of a monosaccharide, which is derived from the open chain of aldoses and ketoses, equivalent to C1 and C2, respectively [5].…”