Selenocysteine derivatives for chemoselective ligations

MD Gieselman, Y Zhu, H Zhou, D Galonic… - …, 2002 - experts.illinois.edu
Selenium variation on a cysteine theme: Selenocysteine (Sec) has been employed in a
number of chemoselective ligations. Sec can be used for native chemical and expressed …

Peptide ligation chemistry at selenol amino acids

LR Malins, NJ Mitchell, RJ Payne - Journal of Peptide Science, 2014 - Wiley Online Library
The convergent assembly of peptide fragments by native chemical ligation has
revolutionized the way in which proteins can be accessed by chemical synthesis. A variation …

Synthesis and semisynthesis of selenopeptides and selenoproteins

J Liu, R Cheng, S Rozovsky - Current opinion in chemical biology, 2018 - Elsevier
Highlights•When selenoester is used for ligation reactions with diselenides, kinetics are
accelerated and side reactions are minimized.•Selenozolidine is emerging as the preferred …

Rapid additive-free selenocystine–selenoester peptide ligation

NJ Mitchell, LR Malins, X Liu… - Journal of the …, 2015 - ACS Publications
We describe an unprecedented reaction between peptide selenoesters and peptide dimers
bearing N-terminal selenocystine that proceeds in aqueous buffer to afford native amide …

Selenium and selenocysteine in protein chemistry

R Mousa, R Notis Dardashti… - Angewandte Chemie …, 2017 - Wiley Online Library
Selenocysteine, the selenium‐containing analogue of cysteine, is the twenty‐first
proteinogenic amino acid. Since its discovery almost fifty years ago, it has been exploited in …

One‐pot ligation–oxidative deselenization at selenocysteine and selenocystine

NJ Mitchell, SS Kulkarni, LR Malins… - … A European Journal, 2017 - Wiley Online Library
The use of native chemical ligation at selenocysteine (Sec) residues with peptide thioesters
and additive‐free selenocystine ligation with peptides bearing phenyl selenoesters, in …

Synthesis of Selenocysteine and Its Derivatives with an Emphasis on Selenenylsulfide ( Se S) Formation

LA Wessjohann, A Schneider - Chemistry & Biodiversity, 2008 - Wiley Online Library
A short survey of historic and current methods for the synthesis of selenocysteine,
selenocystine, and derivatives and related compounds is presented, with an additional …

Synthesis of selenopeptides: an alternative way of incorporating selenocystine

S Aravindhan, HB Singh, M Zeller, RJ Butcher - Amino acids, 2019 - Springer
Selenocysteine (Sec) residue cannot be directly attached to a peptide sequence unless the
selenol form is protected beforehand and several problems have been reported in the …

Synthesis and utility of β-selenophenylalanine and β-selenoleucine in diselenide–selenoester ligation

X Wang, L Corcilius, B Premdjee… - The Journal of Organic …, 2019 - ACS Publications
The synthesis of suitably protected β-selenophenylalanine and β-selenoleucine amino acids
was accomplished from Garner's aldehyde as a common starting point. These selenoamino …

Selenium in peptide chemistry

Ö Pehlivan, M Waliczek, M Kijewska, P Stefanowicz - Molecules, 2023 - mdpi.com
In recent years, researchers have been exploring the potential of incorporating selenium into
peptides, as this element possesses unique properties that can enhance the reactivity of …