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Nitroalkanes as thioacyl equivalents to access thioamides and thiopeptides
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Abstract
Thioamides are an important, but a largely underexplored class of amide bioisostere in peptides. Replacement of oxoamide units with thioamides in peptide therapeutics is a valuable tactic to improve biological activity and resistance to enzymatic hydrolysis. This tactic, however, has been hampered by insufficient methods to introduce thioamide bonds into peptide or protein backbones in a site-specific and stereo-retentive fashion. In this work, we developed an efficient and mild thioacylation method to react nitroalkanes with amines directly in the presence of elemental sulfur and sodium sulfide to form a diverse range of thioamides in high yields. Notably, this convenient method can be employed for the controlled thioamide coupling of multifunctionalized peptides without epimerization of stereocenters, including the late stage thioacylation of advanced compounds of biological and medicinal interest. Experimental interrogation of postulated mechanisms currently supports the intermediacy of thioacyl species.
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Generally, at least two steps are involved in the synthesis of terminal ynamides.
“Generally, at least two steps are involved in the synthesis of terminal ynamides.52”
From Ynamide Coupling Reagents: Origin and Advances (2024) · cites this paper as [52]
The Introduction (page unavailable) describes multistep preparation of thioacylating fragments, not terminal ynamides. Searches for terminal ynamides and their preparation found no passage in our copy stating how many steps their synthesis generally requires. (LLM, conf=0.75)
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Metadata
- Authors
- Wang, X., Xu, S., Tang, Y., Lear, M. J., He, W., & Li, J.
- Affiliations
- Xi'an Jiaotong University (CN)
- University of Lincoln (GB)
- First Affiliated Hospital of Xi'an Jiaotong University (CN)
- Corresponding author
- Li, Jing
- Venue
- Nature Communications
- Published
- 2023-08-02
- Volume
- 14
- Issue
- 1
- Pages
- 4626-4626
- ISSN
- 2041-1723 (ISSN-L)
- PMC
- PMC10397191
- OpenAlex
- W4385493700
- Cited by
- 38
- References
- 53
- Citations by year
- 2026: 6 · 2025: 11 · 2024: 17 · 2023: 4
- FWCI
- 3.39
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Locations
- Nature Communications (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Lincoln Repository (University of Lincoln) (acceptedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Funders
- National Natural Science Foundation of China (22101223)
- Shaanxi Provincial Science and Technology Department (2021QCYRC4-41)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Analysis
- Physical Sciences › Chemistry › Organic Chemistry › Sulfur-Based Synthesis Techniques
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Reactivity of Sulfur-Containing Compounds
- Keywords
- nitroalkanes, thioacylation, thioamides, thiopeptides, peptide therapeutics, elemental sulfur, sodium sulfide, late-stage peptide modification, enzymatic hydrolysis resistance
- MeSH terms
- Amides, Amines, Peptides, Thioamides
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