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Generation of a glycosylated asparagine residue through chemoselective acylation of a glycosylhydrazide.


ABSTRACT: Herein, we report the first selective anomeric N-acylation of a glycosylhydrazide. We show that this transformation can be harnessed to generate amino acid building blocks including FmocAsn(GlcNAc)OH (1), a residue that has been previously shown to be a competent reagent in the solid-phase peptide synthesis of N-linked glycopeptides.

SUBMITTER: Rykaczewski KA 

PROVIDER: S-EPMC7325706 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Generation of a glycosylated asparagine residue through chemoselective acylation of a glycosylhydrazide.

Rykaczewski Katie A KA   Sabourin Kate E KE   Goo Paul J PJ   Griggs Lydia H LH   Jain Saumya S   Reed Paxton A M PAM   Langenhan Joseph M JM  

Carbohydrate research 20200504


Herein, we report the first selective anomeric N-acylation of a glycosylhydrazide. We show that this transformation can be harnessed to generate amino acid building blocks including FmocAsn(GlcNAc)OH (1), a residue that has been previously shown to be a competent reagent in the solid-phase peptide synthesis of N-linked glycopeptides. ...[more]

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