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

Org. Biomol. Chem • 2010
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Publication Information
Authors Alan R. Katritzky, Nader E. Abo-Dya, Abdelmotaal Abdelmajeid, Srinivasa R. Tala, M. S. Amine and
Keywords Not Available
Journal Org. Biomol. Chem
Publisher Not Available
Volume 9
Issue (2)
Pages 596–599
publication.type International
Paper Link Not Available
Supplementary Materials Not Available
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-a-aminoacyl)-
benzotriazoles and N-(Pg-a-dipeptidoyl)benzotriazoles to give larger peptides.