Ynamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis
Abstract
A highly efficient, two-step, one-pot synthetic strategy for amides and peptides was developed by employing ynamides as novel coupling reagents under extremely mild reaction conditions. The ynamides not only are effective for simple amide and dipeptide synthesis but can also be used for peptide segment condensation. Importantly, no racemization was detected during the activation of chiral carboxylic acids. Excellent amidation selectivity toward amino groups in the presence of −OH, −SH, −CONH 2, ArNH 2, and the NH of indole was observed, making the protection of these functional groups unnecessary in amide and peptide synthesis.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
The aminolysis of stable α-acyloxyenamides active ester proceeded smoothly at room temperature to give the target amide in quantitative yield.
“To our delight, the aminolysis of stable α-acyloxyenamides active ester proceeded smoothly at room temperature to give the target amide in a quantitative yield.1”
From Ynamide Coupling Reagents: Origin and Advances (2024) · cites this paper as [1]
Cites
Peptide Coupling Reagents, More than a Letter Soup
El-Faham, A., & Albericio, F. (2011) · Chemical Reviews · doi:10.1021/cr100048w · Cited by 1,245 · see citing works
Subirós‐Funosas, R., Prohens, R., Barbas, R., El‐Faham, A., & Albericio, F. (2009) · Chemistry – A European Journal · doi:10.1002/chem.200900614 · Cited by 421 · see citing works
Umpolung reactivity in amide and peptide synthesis
Shen, B., Makley, D. M., & Johnston, J. N. (2010) · Nature · doi:10.1038/nature09125 · Cited by 318 · see citing works
Kamiński, Z. J., Kolesińska, B., Kolesińska, J., Sabatino, G., Chelli, M., Rovero, P., Błaszczyk, M., Główka, M. L., & Papini, A. M. (2005) · Journal of the American Chemical Society · doi:10.1021/ja054260y · Cited by 155 · see citing works
Palladium-catalyzed hydroacyloxylation of ynamides
Smith, D. L., Goundry, W. R. F., & Lam, H. W. (2012) · Chem. Commun. · doi:10.1039/c1cc13595c · Cited by 95 · see citing works
Xu, S., Liu, J., Hu, D., & Bi, X. (2015) · Green Chemistry · doi:10.1039/c4gc01328j · Cited by 91 · see citing works
Self-citation
Flagged first, then by citations
Cited by
Sorted by citations
Ynamide Coupling Reagents: Origin and Advances
Hu, L., & Zhao, J. (2024) · Accounts of Chemical Research · doi:10.1021/acs.accounts.3c00743 · Cited by 89 · see citing works
Self-citationYnamide‐Mediated Peptide Bond Formation: Mechanistic Study and Synthetic Applications
Xu, S., Jiang, D., Peng, Z., Hu, L., Liu, T., Zhao, L., & Zhao, J. (2022) · Angewandte Chemie International Edition · doi:10.1002/anie.202212247 · Cited by 46 · see citing works
Self-citationYnamide-Mediated Thionoester and Dithioester Syntheses
Yao, C., Yang, J., Lu, X., Zhang, S., & Zhao, J. (2020) · Organic Letters · doi:10.1021/acs.orglett.0c02402 · Cited by 35 · see citing works
Self-citationGuo, Y., Wang, M., Gao, Y., & Liu, G. (2024) · Organic & Biomolecular Chemistry · doi:10.1039/d4ob00563e · Cited by 19 · see citing works
- Authors
- Hu, L., Xu, S., Zhao, Z., Yang, Y., Peng, Z., Yang, M., Wang, C., & Zhao, J.
- Affiliations
- Jiangxi Normal University (CN)
- Corresponding author
- Zhao, Junfeng
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-10-04
- Volume
- 138
- Issue
- 40
- Pages
- 13135-13138
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2525902180
- Cited by
- 267
- References
- 6
- Citations by year
- 2026: 19 · 2025: 22 · 2024: 36 · 2023: 31 · 2022: 32 · 2021: 20 · 2020: 24 · 2019: 27 · 2018: 28 · 2017: 27 · 2016: 1
- FWCI
- 14.38
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Natural Science Foundation of China (21462023)
- Natural Science Foundation of Jiangxi Province (20143ACB20007)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Synthetic Organic Chemistry
- Physical Sciences › Chemistry › Organic Chemistry › Click Chemistry and Applications
- Keywords
- ynamides, coupling reagents, amide synthesis, peptide synthesis, chiral carboxylic acids, one-pot synthesis, dipeptide synthesis
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
