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

Faculty Pharmacy Year: 2011
Type of Publication: Article Pages: 596-599
Authors:
Abo-Dya, Nader E, El-Feky, Said A, Katritzky, Alan R, Tala, Srinivasa R, Abdelmajeid, Abdelmotaal, Amine, M. S
DOI: 10.1039/c0ob00663g
Journal: ORGANIC \& BIOMOLECULAR CHEMISTRY ROYAL SOC CHEMISTRY Volume: 9
Research Area: Chemistry ISSN ISI:000285749800037
Keywords : DBU-Catalyzed transprotection , N-Fmoc-cysteine , , tripeptides into S-Fm-cysteine    
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-alpha-aminoacyl)-benzotriazoles and N-(Pg-alpha-dipeptidoyl)benzotriazoles to give larger peptides.
    
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