One-pot ligation-oxidative deselenization at selenocysteine and selenocystine

Payne, Richard J.; Mitchell, Nicholas J.; Kulkarni, Sameer S.; Wang, Siyao; Malins, Lara

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.

Citation

Payne, R. J., Mitchell, N. J., Kulkarni, S. S., Wang, S., & Malins, L. (2017). One-pot ligation-oxidative deselenization at selenocysteine and selenocystine. Chemistry - A European Journal, 23(4), 946-952. https://doi.org/10.1002/chem.201604709

• Journal Article Type: Article
• Acceptance Date: Nov 15, 2016
• Online Publication Date: Dec 14, 2016
• Publication Date: Jan 18, 2017
• Deposit Date: Dec 12, 2016
• Publicly Available Date: Dec 14, 2016
• Journal: Chemistry - a European Journal
• Print ISSN: 0947-6539
• Electronic ISSN: 1521-3765
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 23
• Issue: 4
• Pages: 946-952
• DOI: https://doi.org/10.1002/chem.201604709
• Keywords: Peptides, Ligation, Oxidative Deselenization, Glycopeptides, Synthesis
• Public URL: https://nottingham-repository.worktribe.com/output/839891
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/chem.201604709/full
• 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.