Silver( <scp>i</scp> )-mediated oxazoline formation: a mild route to 2,4-oxazoles in peptides

We present a silver-promoted cyclization of peptide thioamides that enables site-specific insertion of oxazole and methyloxazole motifs through oxazoline intermediates. Demonstrated in di- and tetrapeptides, this mild, moisture-tolerant methodology delivers high-yield products, offering a robust and general strategy for constructing structurally diverse, conformationally constrained oxazole-containing peptidomimetics.

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Publication Details

Journal
Chemical Science
Published
2025-01-01
DOI
https://doi.org/10.1039/d5sc06351e
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Silver( i )-mediated oxazoline formation: a mild route to 2,4-oxazoles in peptides

Zainab Bello, J. Campbell, Carlie L. Charron, Katherine Cox et al.
Chemical Science
Fluorine in Organic Chemistry
article

Silver( i )-mediated oxazoline formation: a mild route to 2,4-oxazoles in peptides

Zainab Bello, J. Campbell, Carlie L. Charron, Katherine Cox, Erin R. Johnson, Andrew J. Pickett
article en

Abstract

We present a silver-promoted cyclization of peptide thioamides that enables site-specific insertion of oxazole and methyloxazole motifs through oxazoline intermediates. Demonstrated in di- and tetrapeptides, this mild, moisture-tolerant methodology delivers high-yield products, offering a robust and general strategy for constructing structurally diverse, conformationally constrained oxazole-containing peptidomimetics.

Chemical ScienceVol. 16(43)
Dalhousie University (CA), University of Cambridge (GB)
Dalhousie University, Mitacs, Natural Sciences and Engineering Research Council of Canada
Openalex Percentile: Top 79%
Fluorine in Organic Chemistry
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