Département de chimie moléculaire

A review with refs. Among other classes of biomols., carbohydrates and glycoconjugates are widely involved in numerous biol. functions. In addn. to addressing the related synthetic challenges, glyco-chemists have invested intense efforts in providing access to structures that can be used to study, activate, or inhibit these biol. processes. Over the past few decades, aminooxylated carbohydrates have been found to be key building blocks for achieving these goals. This review provides the first in-depth overview covering several aspects related to the syntheses and applications of aminooxylated carbohydrates. After a brief introduction to oxime bonds and their relative stabilities compared to related C=N functions, synthetic aspects of oxime ligation and methodologies for introducing the aminooxy functionality onto both glycofuranosyls and glycopyranosyls are described. The subsequent section focuses on biol. applications involving aminooxylated carbohydrates as components for the construction of mimetic architectures. Mimetics of natural structures represent useful tools for better understanding the features that drive carbohydrate-receptor interactions and their biol. output; they can also function as mimetics and polymers with improved stability and tunable properties. In the next section, multivalent structures such as glycoclusters and glycodendrimers obtained through oxime ligation are described in terms of synthetic design and their biol. applications such as immunomodulators. The second-to-last section discusses misc. applications of oxime-based glycoconjugates, such as enantioselective catalysis and glycosylated oligonucleotides, and conclusions and perspectives are provided in the last section. [on SciFinder(R)]