One-pot ligation-oxidative deselenization at selenocysteine and selenocystine

Payne, Richard J. and Mitchell, Nicholas J. and Kulkarni, Sameer S. and Wang, Siyao and Malins, Lara (2017) One-pot ligation-oxidative deselenization at selenocysteine and selenocystine. Chemistry - a European Journal, 23 (4). pp. 946-952. ISSN 1521-3765

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Abstract

The use of native chemical ligation at selenocysteine (Sec) with peptide thioesters and additive-free selenocystine ligation with peptides bearing phenyl selenoesters, in concert with one-pot oxidative deselenization chemistry, is described. These approaches provide a simple and rapid method for accessing native peptides with serine in place of Sec at the ligation junction. The efficiency of both variants of the one-pot ligation-oxidative deselenization chemistry is probed through the synthesis of a MUC5AC-derived glycopeptide.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: N. J. Mitchell, S. S. Kulkarni, L. R. Malins, S. Wang, R. J. Payne, Chem. Eur. J. 2017, 23, 946 doi:10.1002/chem.201604709 which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/chem.201604709/full This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Keywords: Peptides, Ligation, Oxidative Deselenization, Glycopeptides, Synthesis
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/chem.201604709
Depositing User: Bramwell, Roseanna
Date Deposited: 12 Dec 2016 12:03
Last Modified: 12 Oct 2017 21:59
URI: http://eprints.nottingham.ac.uk/id/eprint/39311

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