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Accueil > Publications > Recherche par années > Années 1990 > 1998

Monsigny, M ; Quetard, C ; Bourgerie, S ; Delay, D ; Pichon, C ; Midoux, P ; Mayer, R ; Roche, AC

Glycotargeting : The preparation of glyco-amino acids and derivatives from unprotected reducing sugars

Biochimie 80 (2) 99-108

par Administrateur - publié le

Abstract :

Lectins are present on the surface of many cells. Many lectins actively recycle from membrane to endosomes and efficiently take up glycoconjugates in a sugar-dependent manner. On this basis, glycoconjugates, specially those obtained by chemical means, are good candidates as carriers of drugs, oligonucleotides or genes. In this paper, we present a panel of methods suitable to transform unprotected reducing oligosaccharides into glycosynthons designed to be easily linked to therapeutic agents. All the glycosynthons presented here are glycosylamines or derivatives, mainly glyco-amino acids or glycopeptides. Glycosylamines are easy to obtain, but they are very labile in slightly acidic or neutral medium ; they must be stabilized, by acylation for instance. The coupling efficiency of a reducing sugar with ammonia as well as an alkylamine or an arylamine is higher at high temperature, however, because of the Amadori rearrangement, special conditions have to be selected to prepare the expected glycosylamine derivative with a high yield.