Issue 14, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
03 Cig 2017
Accepted
10 Cig 2017
First published
13 Cig 2017

Org. Biomol. Chem., 2017,15, 2914-2918

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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