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Issue 14, 2017
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Direct palladium-mediated on-resin disulfide formation from Allocam protected peptides

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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.

Graphical abstract: Direct palladium-mediated on-resin disulfide formation from Allocam protected peptides

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Publication details

The article was received on 03 Mar 2017, accepted on 10 Mar 2017 and first published on 13 Mar 2017


Article type: Communication
DOI: 10.1039/C7OB00536A
Citation: Org. Biomol. Chem., 2017,15, 2914-2918
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    Direct palladium-mediated on-resin disulfide formation from Allocam protected peptides

    T. D. Kondasinghe, H. Y. Saraha, S. B. Odeesho and J. L. Stockdill, Org. Biomol. Chem., 2017, 15, 2914
    DOI: 10.1039/C7OB00536A

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