Selenopeptide chemistry

Muttenthaler, Markus and Alewood, Paul F. (2008) Selenopeptide chemistry. Journal of Peptide Science, 14 12: 1223-1239. doi:10.1002/psc.1075

Author Muttenthaler, Markus
Alewood, Paul F.
Title Selenopeptide chemistry
Journal name Journal of Peptide Science   Check publisher's open access policy
ISSN 1099-1387
Publication date 2008-12-01
Year available 2008
Sub-type Article (original research)
DOI 10.1002/psc.1075
Open Access Status DOI
Volume 14
Issue 12
Start page 1223
End page 1239
Total pages 7
Place of publication Chichester, West Sussex, U.K.
Publisher John Wiley
Language eng
Subject 0304 Medicinal and Biomolecular Chemistry
030406 Proteins and Peptides
Abstract This review focuses on the chemical aspects of the 21st proteinogenic amino acid, selenocysteine in peptides and proteins. It describes the physicochemical properties of selenium/sulfur and selenocysteine/cysteine based on comprehensive structural (X-ray, NMR, CD) and biological data, and illustrates why selenocysteine is considered the most conservative substitution of cysteine. The main focus lies on the synthetic methods on selenocysteine incorporation into peptides and proteins, including an overview of the selenocysteine building block syntheses for Boc- and Fmoc-SPPS. Selenocysteine-mediated reactions such as native chemical ligation and dehydroalanine formation are addressed towards peptide conjugation. Selenopeptides have very interesting and distinct properties which lead to a diverse range of applications such as structural, functional and mechanistic probes, robust scaffolds, enzymatic reaction design, peptide conjugations and folding tools. Copyright © 2008 European Peptide Society and John Wiley & Sons, Ltd.
Keyword Selenium
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
School of Chemistry and Molecular Biosciences
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Citation counts: TR Web of Science Citation Count  Cited 88 times in Thomson Reuters Web of Science Article | Citations
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Created: Wed, 03 Feb 2010, 20:06:51 EST by Macushla Boyle on behalf of Faculty of Science