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DBU-catalyzed transprotection of N-Fmoc-cysteine di- and tripeptides into S-Fm-cysteine di- and tripeptides
Journal article   Peer reviewed

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 and Said A El-Feky
Organic & biomolecular chemistry, Vol.9(2), pp.596-599
21/01/2011
DOI: https://doi.org/10.1039/c0ob00663g
PMID: 21069235

Abstract

Catalysis Cysteine - chemistry Dipeptides - chemistry Molecular Structure Oligopeptides - chemistry Peptides - chemistry Urea - analogs & derivatives Urea - chemistry
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.

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