Toward fully synthetic N-linked glycoproteins

Justin S. Miller; Vadim Y. Dudkin; Gholson J. Lyon; Tom W. Muir; Samuel J. Danishefsky

doi:10.1002/anie.200390131

Toward fully synthetic N-linked glycoproteins

Justin S. Miller, Vadim Y. Dudkin, Gholson J. Lyon, Tom W. Muir, Samuel J. Danishefsky

Research output: Contribution to journal › Article › peer-review

78 Scopus citations

Abstract

Substantial quantities of fully synthetic, homogeneous, N-linked glycopeptides may be accessed by a highly convergent and flexible protocol. Only four transformations are required to generate naturally linked glycopeptides in high yield. Amination of a free glycan is followed by acylation with an asparagine residue of a peptide and Fmoc deprotection; native chemical ligation completes the puzzle to afford N-linked glycopeptides (see scheme). Fmoc=9-fluorenylmethoxycarbonyl.

Original language	English (US)
Pages (from-to)	431-434
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	42
Issue number	4
DOIs	https://doi.org/10.1002/anie.200390131
State	Published - Jan 27 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

Keywords

Carbohydrates
Glycopeptides
Glycosylation
Peptides
Synthetic methods

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10.1002/anie.200390131

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AU - Dudkin, Vadim Y.

AU - Lyon, Gholson J.

AU - Muir, Tom W.

AU - Danishefsky, Samuel J.

PY - 2003/1/27

Y1 - 2003/1/27

N2 - Substantial quantities of fully synthetic, homogeneous, N-linked glycopeptides may be accessed by a highly convergent and flexible protocol. Only four transformations are required to generate naturally linked glycopeptides in high yield. Amination of a free glycan is followed by acylation with an asparagine residue of a peptide and Fmoc deprotection; native chemical ligation completes the puzzle to afford N-linked glycopeptides (see scheme). Fmoc=9-fluorenylmethoxycarbonyl.

AB - Substantial quantities of fully synthetic, homogeneous, N-linked glycopeptides may be accessed by a highly convergent and flexible protocol. Only four transformations are required to generate naturally linked glycopeptides in high yield. Amination of a free glycan is followed by acylation with an asparagine residue of a peptide and Fmoc deprotection; native chemical ligation completes the puzzle to afford N-linked glycopeptides (see scheme). Fmoc=9-fluorenylmethoxycarbonyl.

KW - Carbohydrates

KW - Glycopeptides

KW - Glycosylation

KW - Peptides

KW - Synthetic methods

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ER -

Toward fully synthetic N-linked glycoproteins

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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