Cited by 119Click Chemistry and ApplicationsChemical Synthesis and AnalysisSulfur-Based Synthesis Techniques

Allenamides as Orthogonal Handles for Selective Modification of Cysteine in Peptides and Proteins

Abbas, Ata, Xing, Bengang, Loh, Teck‐Peng·2014·Angewandte Chemie International Edition

Abstract

In this study, a remarkably simple and direct strategy has been successfully developed to selectively label target cysteine residues in fully unprotected peptides and proteins. The strategy is based on the reaction between allenamides and the cysteine thiol, and proceeds swiftly in aqueous medium with excellent selectivity and quantitative conversion, thus forming a stable and irreversible conjugate. The combined simplicity and mildness of the process project allenamide as robust and versatile handles to target cysteines and has potential use in biological systems. Additionally, fluorescent‐labeling studies demonstrated that the installation of a C‐terminal allenamide moiety onto various molecules of interest may supply a new methodology towards the site‐specific labeling of cysteine‐containing proteins. Such a new labeling strategy may thus open a window for its application in the field of life sciences.

Integrity signals

Registry

Crossref · 10.1002/anie.201403121

Cites

17 of 17 references verified0 citation errors · 0 not checkable

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  • The BAPTES terminal allene carboxamide functional group possesses high chemoselectivity toward the thiol side chain of Cys and forms a stable, irreversible conjugate not prone to hydrolysis.

    “The terminal allene carboxamide functional group of the BAPTES ligand possesses high chemoselectivity toward the thiol side chain of Cys, and forms a stable and irreversible conjugate not prone to hydrolysis36.”

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Authors
Abbas, A., Xing, B., & Loh, T.
Affiliations
  • Nanyang Technological University (SG)
  • University of Science and Technology of China (CN)
Corresponding author
  • Xing, Bengang
  • Loh, Teck‐Peng
Venue
Angewandte Chemie International Edition
Publisher
Wiley
Published
2014-05-30
Volume
53
Issue
29
Pages
7491-7494
ISSN
  • 1433-7851 (ISSN-L)
  • 1521-3773
OpenAlex
W4234076445
Cited by
117
References
17
Citations by year
2026: 7 · 2025: 11 · 2024: 12 · 2023: 11 · 2022: 6 · 2021: 11 · 2020: 11 · 2019: 8 · 2018: 12 · 2017: 7 · 2016: 8 · 2015: 9 · 2014: 4
FWCI
4.26
Type
journal article
Language
en
Open access
closed
Locations
  • Angewandte Chemie International Edition (publishedVersion)
  • PubMed (publishedVersion)
  • DR-NTU (Nanyang Technological University) (submittedVersion)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Click Chemistry and Applications
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
  • Physical Sciences › Chemistry › Organic Chemistry › Sulfur-Based Synthesis Techniques
Keywords
allenamides, cysteine labeling, site-specific protein modification, thiol-ene reaction, peptide modification, fluorescent labeling, cysteine-containing proteins
MeSH terms
Amides, Cysteine, Fluorescent Dyes, Peptides, Proteins

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