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Synthesis of (2R)- and (2S)-aminooxy analogues of β-O-glucosylserine and N-oxyamide linked glycoconjugates

Chen, N; Deo, C; Xie, J CHEMISTRYSELECT 2016, 1, 766-770.

Références :

CHEMISTRYSELECT 2016, 1, 766-770.

Auteur(s) : 

Chen, N; Deo, C; Xie, J

Glycosyl amino acids are constituents of glycopeptides and glycoproteins playing important roles in various cellular activities and pathogenic processes. We have stereoselectively synthesized both (2R)- and (2S)-aminooxy analogues of β-O-glucosylserine from sn-(3-β-O-glucosyl)glycerol through selective protection, Mitsunobu reaction, oxidation and Lattrell-Dax epimerization reactions. N-oxyamide linked glycopetides and glycolipids have been prepared from the β-O-glucosyl aminooxy acid derivatives. 1H NMR and IR studies suggest the formation of an α N−O turn structure in the glycopeptide 19.

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Paru le 6 avril 2016
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DOI: 10.1002/slct.201600214

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