Publication

Chemo- and stereoselective glycosylation of hydroxylamino derivatives: A versatile approach to glycoconjugates

1998
Journal Articles

Abstract

A general method for the stereoselective coupling of unprotected oligosaccharides with any substrate containing a N,O-disubstituted hydroxylamine group is described. The cyclic nature of the oligosaccharide reducing unit is preserved and the substrate glycosylated with high diastereoselectivity to sugar through an amino (N[OR2]-) or an aminoxy (N[R-1]-O-) linkage. Due to the uniquely high chemical reactivity and specificity of disubstituted hydroxylamine toward the sugar reducing end, neither protecting groups nor activation methods are required to perform the reaction in aqueous solution. The characteristic features and the scope of this new type of glycosylation reaction are exemplified for the chemoselective synthesis of model glycopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

Official source

https://infoscience.epfl.ch/entities/publication/f7e1af4e-a023-49bd-89e6-35e7b413ac4c

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1998
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/f7e1af4e-a023-49bd-89e6-35e7b413ac4c

About this result

Related concepts (32)

N-linked glycosylation

N-linked glycosylation, is the attachment of an oligosaccharide, a carbohydrate consisting of several sugar molecules, sometimes also referred to as glycan, to a nitrogen atom (the amide nitrogen of an asparagine (Asn) residue of a protein), in a process called N-glycosylation, studied in biochemistry. The resulting protein is called an N-linked glycan, or simply an N-glycan. This type of linkage is important for both the structure and function of many eukaryotic proteins.

Glycosylation

Glycosylation is the reaction in which a carbohydrate (or 'glycan'), i.e. a glycosyl donor, is attached to a hydroxyl or other functional group of another molecule (a glycosyl acceptor) in order to form a glycoconjugate. In biology (but not always in chemistry), glycosylation usually refers to an enzyme-catalysed reaction, whereas glycation (also 'non-enzymatic glycation' and 'non-enzymatic glycosylation') may refer to a non-enzymatic reaction. Glycosylation is a form of co-translational and post-translational modification.

Chemical glycosylation

A chemical glycosylation reaction involves the coupling of a glycosyl donor, to a glycosyl acceptor forming a glycoside. If both the donor and acceptor are sugars, then the product is an oligosaccharide. The reaction requires activation with a suitable activating reagent. The reactions often result in a mixture of products due to the creation of a new stereogenic centre at the anomeric position of the glycosyl donor.

Related publications (2)

Chemo- and stereoselective glycosylation of hydroxylamino derivatives: A versatile approach to glycoconjugates

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Method for preparation of pentopyranosyl nucleosides

Enantiomerically Pure 7-Oxabicyclo[2.2.1]Hept-5-En-2-Yl Derivatives as Synthetic Intermediates .16. Total Asymmetric-Synthesis of 6-Deoxy-5-C-Methyl-D-Ribo-Hexose Structure in Aqueous-Solution