Diselenide–selenoester ligation for chemical protein synthesis

SS Kulkarni, EE Watson, B Premdjee… - Nature …, 2019 - nature.com
Chemoselective peptide ligation methods have provided synthetic access to numerous
proteins, including those bearing native post-translational modifications and unnatural …

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 …

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 …

Solid phase synthesis of peptide-selenoesters

A Ghassemian, X Vila-Farrés, PF Alewood… - Bioorganic & medicinal …, 2013 - Elsevier
The synthesis of proteins by native chemical ligation greatly enhances the application of
chemistry to complex molecules such as proteins. The essential building blocks for this …

Native chemical ligation combined with desulfurization and deselenization: a general strategy for chemical protein synthesis

PE Dawson - Israel Journal of Chemistry, 2011 - Wiley Online Library
Of the many approaches proposed to generalize the native chemical ligation approach for
protein synthesis, the simple procedure of global desulfurization of peptide thiols has …

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 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 …

[HTML][HTML] Traceless ligation of cysteine peptides using selective deselenization

N Metanis, E Keinan, PE Dawson - … Chemie (International ed. in …, 2010 - ncbi.nlm.nih.gov
The synthesis of proteins with a fully native sequence is an ongoing challenge in protein
chemistry. Native chemical ligation (NCL) approaches have proven to be generally …

Solid-phase synthesis of peptide selenoesters via a side-chain anchoring strategy

CC Hanna, SS Kulkarni, EE Watson… - Chemical …, 2017 - pubs.rsc.org
Peptide selenoesters have recently emerged as key building blocks for the ligation-based
assembly of large polypeptides and proteins. Herein, we report an efficient solid-phase …

Utilizing selenocysteine for expressed protein ligation and bioconjugations

J Liu, Q Chen, S Rozovsky - Journal of the American Chemical …, 2017 - ACS Publications
Employing selenocysteine-containing protein fragments to form the amide bond between
respective protein fragments significantly extends the current capabilities of the widely used …