The DOI matches its Crossref record; 12 of the 12 references it cites were found in a registry or an index.
Site-Selective C(sp3)–H Functionalization of Di-, Tri-, and Tetrapeptides at the N-Terminus
Open accessAbstract
Although the syntheses of novel and diverse peptides rely mainly on traditional coupling using unnatural amino acids, postsynthetic modification of peptides could provide a complementary method for the preparation of nonproteinogenic peptides. Site selectivity of postsynthetic modification of peptides is usually achieved by targeting reactive moieties, such as the thiol group of cysteine or the C-2 position of tryptophan. Herein, we report the development of site-selective functionalizations of inert C(sp(3))-H bonds of N-terminal amino acids in di-, tri-, and tetrapeptides without installing a directing group. The native amino acid moiety within the peptide is used as a ligand to accelerate the C-H activation reaction. In the long run, this newly uncovered reactivity could provide guidance for developing site-selective C(sp(3))-H activation toward postsynthetic modification of a broader range of peptides.
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Citations
Cites
Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions
Lyons, T. W., & Sanford, M. S. (2010) · Chemical Reviews · doi:10.1021/cr900184e · Cited by 6,119
The Future of Peptide‐based Drugs
Craik, D. J., Fairlie, D. P., Liras, S., & Price, D. (2013) · Chemical Biology & Drug Design · doi:10.1111/cbdd.12055 · Cited by 1,979
Future directions for peptide therapeutics development
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Novel Acetoxylation and C−C Coupling Reactions at Unactivated Positions in α-Amino Acid Derivatives
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A “Tag-and-Modify” Approach to Site-Selective Protein Modification
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Ligand-enabled cross-coupling of C(sp3)–H bonds with arylboron reagents via Pd(II)/Pd(0) catalysis
Chan, K. S. L., Wasa, M., Chu, L., Laforteza, B. N., Miura, M., & Yu, J.-Q. (2014) · Nature Chemistry · doi:10.1038/nchem.1836 · Cited by 230
Self-citationStudying protein–protein interactions using peptide arrays
Katz, C., Levy-Beladev, L., Rotem-Bamberger, S., Rito, T., Rüdiger, S. G. D., & Friedler, A. (2011) · Chemical Society Reviews · doi:10.1039/c0cs00029a · Cited by 186
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Self-citationModification of N-Terminal α-Amino Groups of Peptides and Proteins Using Ketenes
Chan, A. O.-Y., Ho, C.-M., Chong, H.-C., Leung, Y.-C., Huang, J.-S., Wong, M.-K., & Che, C.-M. (2012) · Journal of the American Chemical Society · doi:10.1021/ja208009r · Cited by 169
Huang, R., Holbert, M. A., Tarrant, M. K., Curtet, S., Colquhoun, D. R., Rabbitts, B. M., Dancy, B. C. R., Hwang, Y., Tang, Y., Meeth, K. M., et al. (2010) · Journal of the American Chemical Society · doi:10.1021/ja103954u · Cited by 119
Allenamides as Orthogonal Handles for Selective Modification of Cysteine in Peptides and Proteins
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Peptidic macrocyclization via palladium-catalyzed chemoselective indole C-2 arylation
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Cited by
Palladium-Catalyzed Transformations of Alkyl C–H Bonds
He, J., Wasa, M., Chan, K. S. L., Shao, Q., & Yu, J.-Q. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00622 · Cited by 2,036
Self-citationLate-stage C–H functionalization offers new opportunities in drug discovery
Guillemard, L., Kaplaneris, N., Ackermann, L., & Johansson, M. J. (2021) · Nature Reviews Chemistry · doi:10.1038/s41570-021-00300-6 · Cited by 837
C–H Activation: Toward Sustainability and Applications
Dalton, T., Faber, T., & Glorius, F. (2021) · ACS Central Science · doi:10.1021/acscentsci.0c01413 · Cited by 833
Motiwala, H. F., Armaly, A. M., Cacioppo, J. G., Coombs, T. C., Koehn, K. R. K., Norwood, V. M., & Aubé, J. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00749 · Cited by 593
Transition-Metal-Catalyzed C–H Bond Activation for the Formation of C–C Bonds in Complex Molecules
Docherty, J. H., Lister, T. M., Mcarthur, G., Findlay, M. T., Domingo-Legarda, P., Kenyon, J., Choudhary, S., & Larrosa, I. (2023) · Chemical Reviews · doi:10.1021/acs.chemrev.2c00888 · Cited by 593
Metadata
- Authors
- Gong, W., Zhang, G., Liu, T., Giri, R., & Yu, J.-Q.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2014-11-20
- Volume
- 136
- Issue
- 48
- Pages
- 16940-16946
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2315874011
- Cited by
- 288
- References
- 12
- FWCI
- 11.13
- Type
- journal article
- Language
- en
- Open access
- hybrid
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