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Allenamides as Orthogonal Handles for Selective Modification of Cysteine in Peptides and Proteins
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.
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“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.”
From Nanoproteomics enables proteoform-resolved analysis of low-abundance proteins in human serum (2020) · cites this paper as [36]
Citations
Cites
Chemical Modification of Proteins at Cysteine: Opportunities in Chemistry and Biology
Chalker, J. M., Bernardes, G. J. L., Lin, Y. A., & Davis, B. G. (2009) · Chemistry - An Asian Journal · doi:10.1002/asia.200800427 · Cited by 653
Protein Modification, Bioconjugation, and Disulfide Bridging Using Bromomaleimides
Smith, M. E. B., Schumacher, F. F., Ryan, C. P., Tedaldi, L. M., Papaioannou, D., Waksman, G., Caddick, S., & Baker, J. R. (2010) · Journal of the American Chemical Society · doi:10.1021/ja908610s · Cited by 378
On Terminal Alkynes That Can React with Active-Site Cysteine Nucleophiles in Proteases
Ekkebus, R., van Kasteren, S. I., Kulathu, Y., Scholten, A., Berlin, I., Geurink, P. P., de Jong, A., Goerdayal, S. S., Neefjes, J., Heck, A. J. R., et al. (2013) · Journal of the American Chemical Society · doi:10.1021/ja309802n · Cited by 346
Lin, Y. A., Chalker, J. M., Floyd, N., Bernardes, G. J. L., & Davis, B. G. (2008) · Journal of the American Chemical Society · doi:10.1021/ja8026168 · Cited by 330
Occurrence, conformational features and amino acid propensities for the π-helix
Fodje, M. N., & Al‐Karadaghi, S. (2002) · Protein Engineering Design and Selection · doi:10.1093/protein/15.5.353 · Cited by 272
Site-Specific PEGylation of Protein Disulfide Bonds Using a Three-Carbon Bridge
Balan, S., Choi, J.-W., Godwin, A., Teo, I. A., Laborde, C. M., Heidelberger, S., Zloh, M., Shaunak, S., & Brocchini, S. (2006) · Bioconjugate Chemistry · doi:10.1021/bc0601471 · Cited by 172
Conjugation-Induced Fluorescent Labeling of Proteins and Polymers Using Dithiomaleimides
Robin, M. P., Wilson, P., Mabire, A. B., Kiviaho, J. K., Raymond, J. E., Haddleton, D. M., & O’Reilly, R. K. (2013) · Journal of the American Chemical Society · doi:10.1021/ja3105494 · Cited by 123
Shiu, H., Chan, T. H., Ho, C., Liu, Y., Wong, M., & Che, C. (2009) · Chemistry - A European Journal · doi:10.1002/chem.200800669 · Cited by 121
Sommer, S., Weikart, N. D., Linne, U., & Mootz, H. D. (2013) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2013.02.039 · Cited by 115
Bromomaleimides: new reagents for the selective and reversible modification of cysteine
Tedaldi, L. M., Smith, M. E. B., Nathani, R. I., & Baker, J. R. (2009) · Chemical Communications · doi:10.1039/b915136b · Cited by 108
Functionalization of Peptides and Proteins by Mukaiyama Aldol Reaction
Alam, J., Keller, T. H., & Loh, T. (2010) · Journal of the American Chemical Society · doi:10.1021/ja102733a · Cited by 67
Self-citationAllylic Selenosulfide Rearrangement: A Method for Chemical Ligation to Cysteine and Other Thiols
Crich, D., Krishnamurthy, V., & Hutton, T. K. (2006) · Journal of the American Chemical Society · doi:10.1021/ja057521c · Cited by 56
Gold-mediated selective cysteine modification of peptides using allenes
Chan, A. O., Tsai, J. L., Lo, V. K., Li, G.-L., Wong, M., & Che, C. (2013) · Chemical Communications · doi:10.1039/c2cc38214h · Cited by 54
The preparation of the first α-vinylidene-β-lactams
Buynak, J. D., Mathew, J., Rao, M. N., Haley, E., George, C., & Siriwardane, U. (1987) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39870000735 · Cited by 33
Arkona, C., & Rademann, J. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201303544 · Cited by 25
Roedig, A., & Ritschel, W. (1983) · Chemische Berichte · doi:10.1002/cber.19831160434 · Cited by 14
Arkona, C., & Rademann, J. (2013) · Angewandte Chemie · doi:10.1002/ange.201303544 · Cited by 4
Research works printed but not linked: 1
- Kostikov R. R., 2005, Science of Synthesis, Vol. 24, 17
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Advances in Chemical Protein Modification
Boutureira, O., & Bernardes, G. J. L. (2015) · Chemical Reviews · doi:10.1021/cr500399p · Cited by 1,137
Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation
McKay, C. S., & Finn, M. G. (2014) · Chemistry & Biology · doi:10.1016/j.chembiol.2014.09.002 · Cited by 804
Gehringer, M., & Laufer, S. (2018) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.8b01153 · Cited by 772
Residue-Specific Peptide Modification: A Chemist’s Guide
deGruyter, J. N., Malins, L. R., & Baran, P. S. (2017) · Biochemistry · doi:10.1021/acs.biochem.7b00536 · Cited by 571
Contemporary approaches to site-selective protein modification
Hoyt, E. A., Cal, P. M. S. D., Oliveira, B. L., & Bernardes, G. J. L. (2019) · Nature Reviews Chemistry · doi:10.1038/s41570-019-0079-1 · Cited by 542
Metadata
- 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
- Physical Sciences › Chemistry › Organic Chemistry › 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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