Selenopeptide chemistry

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, (c) 2008 European Peptide Society and John Wiley & Sons, Ltd.