Work

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

Year: 2017

Type: article

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.

Source: Organic & Biomolecular Chemistry

DOI: 10.1039/c7ob00536a

Authors: Thilini D. Kondasinghe, Hasina Y. Saraha, Samantha B. Odeesho, Jennifer L. Stockdill

Institution: Wayne State University

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: Wayne State University, National Institute of General Medical Sciences

Award: C-N Bond-Forming Methodologies for the Synthesis of Small Molecules and Peptides