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One-pot ligation-oxidative deselenization at selenocysteine and selenocystine

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

Authors

Richard J. Payne

Nicholas J. Mitchell

Sameer S. Kulkarni

Siyao Wang

Lara Malins



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.

Journal Article Type Article
Publication Date Jan 18, 2017
Journal Chemistry - a European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 23
Issue 4
APA6 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), doi:10.1002/chem.201604709
DOI https://doi.org/10.1002/chem.201604709
Keywords Peptides, Ligation, Oxidative Deselenization, Glycopeptides, Synthesis
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/chem.201604709/full
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
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.wi...002/chem.201604709/full This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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