Aminooxylated Carbohydrates: Synthesis and Applications

• Published in: Chemical reviews 2017-08, Vol.117 (15), p.9839-9873
• Main Authors: Pifferi, Carlo, Daskhan, Gour Chand, Fiore, Michele, Shiao, Tze Chieh, Roy, René, Renaudet, Olivier
• Format: Article
• Language: English
• Subjects: Analytical chemistry; Biological activity; Biomolecules; Carbohydrates; Carbohydrates - chemical synthesis; Carbohydrates - chemistry; Catalysis; Chemical compounds; Chemical Sciences; Chemical synthesis; Glycoproteins - chemistry; Immunomodulators; Molecules; Oligonucleotides; Oligonucleotides - chemistry; Stereoisomerism; Structural stability
• ISSN: 0009-2665; 1520-6890
• DOI: 10.1021/acs.chemrev.6b00733

Among other classes of biomolecules, carbohydrates and glycoconjugates are widely involved in numerous biological functions. In addition to addressing the related synthetic challenges, glycochemists have invested intense efforts in providing access to structures that can be used to study, activate, or inhibit these biological 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 biological applications involving aminooxylated carbohydrates as components for the construcion of diverse architectures. Mimetics of natural structures represent useful tools for better understanding the features that drive carbohydrate–receptor interaction, their biological output and they also represent interesting structures 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 biological applications such as immunomodulators. The second-to-last section discusses miscellaneous applications of oxime-based glycoconjugates, such as enantioselective catalysis and glycosylated oligonucleotides, and conclusions and perspectives are provided in the last section.