ArticleOrganic & biomolecular chemistry2017
Direct palladium-mediated on-resin disulfide formation from Allocam protected peptides.
Article in Organic & biomolecular chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed, 16 citations in OpenAlex.
- Emerging Trends in Cross-Coupling: Twelve-Electron-Based LChemical reviews · 2022Review
- Raising the Bar On-Bead: Efficient On-Resin Synthesis of α-Conotoxin LvIA.Tetrahedron letters · 2019Article
- Epimerization-free access to C-terminal cysteine peptide acids, carboxamides, secondary amides, and estersChemical science · 2018Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
The synthesis of disulfide-containing polypeptides represents a long-standing challenge in peptide chemistry, and broadly applicable methods for the construction of disulfides are in constant demand. Few strategies exist for on-resin formation of disulfides directly from their protected counterparts. We present herein a novel strategy for the on-resin construction of disulfides directly from Allocam-protected cysteines. Our palladium-mediated approach is mild and uses readily available reagents, requiring no special equipment. No reduced peptide intermediates or S-allylated products are observed, and no residual palladium can be detected in the final products. The utility of this method is demonstrated through the synthesis of the C-carboxy analog of oxytocin.
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