The DOI matches its Crossref record; 46 of the 46 references it cites were found in a registry or an index.
Construction of Thioamide Peptides from Chiral Amino Acids
Abstract
Thioamide peptides were synthesized in a straightforward one‐pot process via the linkage of diverse natural amino acids in the presence of thiolphosphonate and trichlorosilane, wherein carbonyl groups were replaced with thiono compounds with minimal racemization. Experimental and computational mechanistic studies demonstrated that the trichlorosilane enables the activation of carboxylic acids via intense interactions with the Si−O bond, followed by coupling of the carboxylic acids with thiolphosphonate to obtain the key intermediate S‐acyl dithiophosphate. Silyl‐activated quadrangular metathesis transition states afforded the thioamide peptides. The potential applications of these thioamide peptides were further highlighted via late‐stage linkages of diverse natural products and pharmaceutical drugs and the thioamide moiety.
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“To make ynamides readily available coupling reagents, we have developed a robust one-step synthetic approach for producing MYTsA and MYMsA with 1,1- or 1,2-dichloroethylene, and N,4-dimethylbenzenesulfonamide (TsNHMe) or N-methylmethanesulfonamide (MsNHMe) as the starting materials (Scheme 10a).53”
From Ynamide Coupling Reagents: Origin and Advances (2024) · cites this paper as [53]
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Cites
Shermo: A general code for calculating molecular thermochemistry properties
Lu, T., & Chen, Q. (2021) · Computational and Theoretical Chemistry · doi:10.1016/j.comptc.2021.113249 · Cited by 1,402
Construction of sulfur-containing moieties in the total synthesis of natural products
Wang, N., Saidhareddy, P., & Jiang, X. (2020) · Natural Product Reports · doi:10.1039/c8np00093j · Cited by 750
Self-citationThionation reactions of lawesson's reagents
Cava, M. P., & Levinson, M. I. (1985) · Tetrahedron · doi:10.1016/s0040-4020(01)96753-5 · Cited by 667
Use of Lawesson's Reagent in Organic Syntheses
Ozturk, T., Ertas, E., & Mert, O. (2007) · Chemical Reviews · doi:10.1021/cr040650b · Cited by 500
Thioamides as Useful Synthons in the Synthesis of Heterocycles
Jagodziński, T. S. (2003) · Chemical Reviews · doi:10.1021/cr0200015 · Cited by 486
From Amino Acids to Heteroaromatics—Thiopeptide Antibiotics, Nature's Heterocyclic Peptides
Hughes, R. A., & Moody, C. J. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200700728 · Cited by 269
An Evaluation of Peptide‐Bond Isosteres
Choudhary, A., & Raines, R. T. (2011) · ChemBioChem · doi:10.1002/cbic.201100272 · Cited by 259
Selective Late‐Stage Oxygenation of Sulfides with Ground‐State Oxygen by Uranyl Photocatalysis
Li, Y., Rizvi, S. A., Hu, D., Sun, D., Gao, A., Zhou, Y., Li, J., & Jiang, X. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201906080 · Cited by 246
Self-citationJing, H., Hu, J., He, B., Negrón Abril, Y. L., Stupinski, J., Weiser, K., Carbonaro, M., Chiang, Y.-L., Southard, T., Giannakakou, P., et al. (2016) · Cancer Cell · doi:10.1016/j.ccell.2016.02.007 · Cited by 229
Xiao, X., Feng, M., & Jiang, X. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201608011 · Cited by 227
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Research works printed but not linked: 1
- Deposition Numbers2123840 (for3l) and 2152203 (for4c)contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service.
Cited by
Ynamide Coupling Reagents: Origin and Advances
Hu, L., & Zhao, J. (2024) · Accounts of Chemical Research · doi:10.1021/acs.accounts.3c00743 · Cited by 89
Metadata
- Authors
- Liao, Y., Zhang, S., & Jiang, X.
- Affiliations
- East China Normal University (CN)
- Chinese Academy of Sciences (CN)
- Corresponding author
- Jiang, Xuefeng
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2023-05-15
- Volume
- 62
- Issue
- 26
- Pages
- e202303625-e202303625
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W4367369316
- Cited by
- 27
- References
- 46
- Citations by year
- 2026: 6 · 2025: 7 · 2024: 9 · 2023: 5
- FWCI
- 2.39
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Outstanding Youth Science Fund Project of National Natural Science Foundation of China (22125103 and 21971065)
- Science and Technology Commission of Shanghai Municipality (22JC1401000, 20JC1416800, and 20XD1421500)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Analysis
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Reactivity of Sulfur-Containing Compounds
- Physical Sciences › Chemistry › Organic Chemistry › Sulfur-Based Synthesis Techniques
- Keywords
- chiral amino acids, trichlorosilane, carboxylic acid activation, transition state, racemization, late-stage functionalization, natural products, pharmaceutical drugs
- MeSH terms
- Amines, Amino Acids, Carboxylic Acids, Peptides, Silanes, Thioamides
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- Liao, Y., Zhang, S., & Jiang, X. (2023). Construction of Thioamide Peptides from Chiral Amino Acids. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.202303625
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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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