DBU-Catalyzed transprotection of N-Fmoc-cysteine di- and tripeptides into S-Fm-cysteine di- and tripeptides

Alan R. Katritzky, Nader E. Abo-Dya, Abdelmotaal Abdelmajeid, Srinivasa R. Tala, M. S. Amine, Said A. El-Feky

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

The transprotection of N-Fmoc-cysteine containing di- and tripeptides possessing a free SH group to produce the corresponding S-Fm-cysteine di- and tripeptides bearing a free amino group is accomplished efficiently with DBU in dry THF. The N-Fmoc to S-Fm transformation mechanism is discussed. S-Fm-Cysteine di- and tripeptides readily form amide bonds on coupling with N-(Pg-α-aminoacyl)benzotriazoles and N-(Pg-α-dipeptidoyl) benzotriazoles to give larger peptides.

Original languageEnglish (US)
Pages (from-to)596-599
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number2
DOIs
StatePublished - Jan 21 2011

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