Synthesis and utility of β-selenol-phenylalanine for native chemical ligation–deselenization chemistry

LR Malins, RJ Payne - Organic letters, 2012 - ACS Publications
An efficient synthetic route to a suitably protected β-selenol-phenylalanine derivative from
commercially available Garner's aldehyde is described. The incorporation of this building …

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 …

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 …

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 …

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 …

Preparation of Peptide Selenoesters from Their Corresponding Acyl Hydrazides

Y Li, J Liu, Q Zhou, J Zhao… - Chinese Journal of …, 2021 - Wiley Online Library
Main observation and conclusion Selenoesters are useful substitutes for traditional
thioesters in protein ligation chemistry due to their high reactivity in the trans‐thio …

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 …

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 …

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 …

Straightforward Synthesis of Non‐Natural Selenium Containing Amino Acid Derivatives and Peptides

AL Braga, DS Lüdtke, MW Paixão, EE Alberto… - 2005 - Wiley Online Library
A series of non‐natural selenium‐containing amino acid derivatives and peptides have
been synthesized, in a flexible and modular strategy. The peptide coupling reaction between …