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Molecules 2018, 23(3), 641; https://doi.org/10.3390/molecules23030641

Synthesis of O-Amino Sugars and Nucleosides

1
and
2,*
1
School of Biomedical Sciences, Huaqiao University, Xiamen 361021, China
2
PPSM, ENS Paris-Saclay, Institut d’Alembert, CNRS, Université Paris-Saclay, 94235 Cachan, France
*
Author to whom correspondence should be addressed.
Received: 25 January 2018 / Revised: 26 February 2018 / Accepted: 9 March 2018 / Published: 12 March 2018
(This article belongs to the Special Issue Glycomimetics: Design, Synthesis and Therapeutic Applications)
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Abstract

Nucleic acids and carbohydrates are essential biomolecules involved in numerous biological and pathological processes. Development of multifunctional building blocks based on nucleosides and sugars is in high demand for the generation of novel oligonucleotide mimics and glycoconjugates for biomedical applications. Recently, aminooxyl-functionalized compounds have attracted increasing research interest because of their easy derivatization through oxime ligation or N-oxyamide formation reactions. Various biological applications have been reported for O-amino carbohydrate- and nucleoside-derived compounds. Here, we report our efforts in the design and synthesis of glyco-, glycosyl, nucleoside- and nucleo-aminooxy acid derivatives from readily available sugars and amino acids, and their use for the generation of N-oxyamide-linked oligosaccharides, glycopeptides, glycolipids, oligonucleosides and nucleopeptides as novel glycoconjugates or oligonucleotide mimics. Delicate and key points in the synthesis will be emphasized. View Full-Text
Keywords: sugar aminooxy acid; glycosyl aminooxy acid; N-oxyamide; oligosaccharide; glycolipid; glycopeptide; O-amino nucleoside; nucleo-aminooxy acid sugar aminooxy acid; glycosyl aminooxy acid; N-oxyamide; oligosaccharide; glycolipid; glycopeptide; O-amino nucleoside; nucleo-aminooxy acid
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Chen, N.; Xie, J. Synthesis of O-Amino Sugars and Nucleosides. Molecules 2018, 23, 641.

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