title: N-O linkage in carbohydrates and glycoconjugates.
abstract: The importance of oligosaccharides and their conjugates in various biological and pathological processes has stimulated growing interest in the development of (neo)glycoconjugates. Thanks to its high nucleophilicity, hydroxylamine has been employed as a powerful chemoselective ligation tool. Great effort has been focused on carbohydrates bearing aminooxy or N-hydroxy amino groups for organic synthesis, glycobiology and drug discovery. This review provides an overview of N-O linked carbohydrates and glycoconjugates, focusing particularly on the synthetic methodologies and chemical and physicochemical properties as well as biological and medical applications of N-glycosyl and O-glycosyl hydroxylamines, N-hydroxy amino and O-amino sugar as well as sugar aminooxy acid derivatives.
authors: PPSM, ENS Cachan, CNRS, Alembert Institute, Université Paris-Saclay, Cachan, 94235, France. joanne.xie@ens-cachan.fr and School of Biomedical Sciences, Huaqiao University, Xiamen 361021, China.
authors: N
authors: N
authors: Chen
authors: PPSM, ENS Cachan, CNRS, Alembert Institute, Université Paris-Saclay, Cachan, 94235, France. joanne.xie@ens-cachan.fr.
authors: J
authors: J
authors: Xie
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D006001:Glycoconjugates / Q000737:chemistry*; D006031:Glycosylation; D019811:Hydroxylamine / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D006001:Glycoconjugates; D019811:Hydroxylamine; D009584:Nitrogen; D010100:Oxygen