Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 14, 2017
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
03 Mar 2017
Accepted
10 Mar 2017
First published
13 Mar 2017

Org. Biomol. Chem., 2017,15, 2914-2918
Article type
Communication

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

Social activity

Search articles by author

Spotlight

Advertisements