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Facile Chemoselective Synthesis of Dehydroalanine-Containing Peptides
Abstract
Useful methodology is described for the synthesis of dehydroalanine residues (II) within peptides. The unnatural amino acid (Se)-phenylselenocysteine (I) can be incorporated into growing peptide chains via standard peptide synthesis procedures. Subsequent oxidative elimination affords a dehydroalanine at the desired position. The oxidation conditions are mild and tolerate functionalities commonly found in peptides, including variously protected cysteine residues. To illustrate its utility, cyclic lanthionines have been synthesized by this method.
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Cited by
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 649
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 573
Algar, W. R., Prasuhn, D. E., Stewart, M. H., Jennings, T. L., Blanco-Canosa, J. B., Dawson, P. E., & Medintz, I. L. (2011) · Bioconjugate Chemistry · doi:10.1021/bc200065z · Cited by 502
Methods for converting cysteine to dehydroalanine on peptides and proteins
Chalker, J. M., Gunnoo, S. B., Boutureira, O., Gerstberger, S. C., Fernández-González, M., Bernardes, G. J. L., Griffin, L., Hailu, H., Schofield, C. J., & Davis, B. G. (2011) · Chemical Science · doi:10.1039/c1sc00185j · Cited by 367
Ribosomal peptide natural products: bridging the ribosomal and nonribosomal worlds
McIntosh, J. A., Donia, M. S., & Schmidt, E. W. (2009) · Natural Product Reports · doi:10.1039/b714132g · Cited by 269
Histones: At the Crossroads of Peptide and Protein Chemistry
Müller, M. M., & Muir, T. W. (2015) · Chemical Reviews · doi:10.1021/cr5003529 · Cited by 247
Selenium‐containing amino acids as direct and indirect antioxidants
Rahmanto, A. S., & Davies, M. J. (2012) · IUBMB Life · doi:10.1002/iub.1084 · Cited by 144
Metadata
- Authors
- Okeley, N. M., Zhu, Y., & van der Donk, W. A.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-10-24
- Volume
- 2
- Issue
- 23
- Pages
- 3603-3606
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2047654005
- Cited by
- 165
- References
- 0
- FWCI
- 2.03
- Type
- journal article
- Language
- en
- Open access
- closed
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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