Utilizing Copper-Mediated Deprotection of Selenazolidine for Cyclic Peptide Synthesis

Zhenguang Zhao, Norman Metanis*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Selenazoliline (Sez) was originally developed as a masked form of selenocysteine (Sec) for the chemical synthesis of challenging proteins. Here, we utilize Sez and our recently reported copper(II)-mediated deprotection for the synthesis of cyclic peptides. This approach allowed one-pot deprotection, cyclization, and deselenization to give several different cyclic peptides in good yields. In Sez-mediated peptide cyclization, the Sec can also be retained, which enhances the oxidative folding of disulfide-rich cyclic proteins such in the case of Kalata S.

Original languageAmerican English
Pages (from-to)1731-1739
Number of pages9
JournalJournal of Organic Chemistry
Volume85
Issue number3
DOIs
StatePublished - 7 Feb 2020

Bibliographical note

Publisher Copyright:
Copyright © 2019 American Chemical Society.

Fingerprint

Dive into the research topics of 'Utilizing Copper-Mediated Deprotection of Selenazolidine for Cyclic Peptide Synthesis'. Together they form a unique fingerprint.

Cite this