One-Pot Peptide Ligation–Desulfurization at Glutamate

Katie M. Cergol; Robert E. Thompson; Lara R. Malins; Peter Turner; Richard J. Payne

doi:10.1021/ol403288n

One-Pot Peptide Ligation–Desulfurization at Glutamate

Katie M. Cergol, Robert E. Thompson, Lara R. Malins, Peter Turner, Richard J. Payne^*

^*Corresponding author for this work

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

68 Citations (Scopus)

Abstract

An efficient methodology for ligation at glutamate (Glu) is described. A γ-thiol-Glu building block was accessed in only three steps from protected glutamic acid and could be incorporated at the N-terminus of peptides. The application of these peptides in one-pot ligation-desulfurization chemistry is demonstrated with a range of peptide thioesters, and the utility of this methodology is highlighted through the synthesis of the osteoporosis peptide drug teriparatide (Forteo).

Original language	English
Pages (from-to)	290-293
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	1
Early online date	2 Dec 2013
DOIs	https://doi.org/10.1021/ol403288n
Publication status	Published - 3 Jan 2014
Externally published	Yes

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10.1021/ol403288n

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abstract = "An efficient methodology for ligation at glutamate (Glu) is described. A γ-thiol-Glu building block was accessed in only three steps from protected glutamic acid and could be incorporated at the N-terminus of peptides. The application of these peptides in one-pot ligation-desulfurization chemistry is demonstrated with a range of peptide thioesters, and the utility of this methodology is highlighted through the synthesis of the osteoporosis peptide drug teriparatide (Forteo).",

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AU - Cergol, Katie M.

AU - Thompson, Robert E.

AU - Malins, Lara R.

AU - Turner, Peter

AU - Payne, Richard J.

PY - 2014/1/3

Y1 - 2014/1/3

N2 - An efficient methodology for ligation at glutamate (Glu) is described. A γ-thiol-Glu building block was accessed in only three steps from protected glutamic acid and could be incorporated at the N-terminus of peptides. The application of these peptides in one-pot ligation-desulfurization chemistry is demonstrated with a range of peptide thioesters, and the utility of this methodology is highlighted through the synthesis of the osteoporosis peptide drug teriparatide (Forteo).

AB - An efficient methodology for ligation at glutamate (Glu) is described. A γ-thiol-Glu building block was accessed in only three steps from protected glutamic acid and could be incorporated at the N-terminus of peptides. The application of these peptides in one-pot ligation-desulfurization chemistry is demonstrated with a range of peptide thioesters, and the utility of this methodology is highlighted through the synthesis of the osteoporosis peptide drug teriparatide (Forteo).

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One-Pot Peptide Ligation–Desulfurization at Glutamate

Abstract

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