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

Autor: Katritzky AR; Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA. katritzky@chem.ufl.edu, Abo-Dya NE, Abdelmajeid A, Tala SR, Amine MS, El-Feky SA
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2011 Jan 21; Vol. 9 (2), pp. 596-9. Date of Electronic Publication: 2010 Nov 10.
DOI: 10.1039/c0ob00663g
Abstrakt: 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.
Databáze: MEDLINE