Issue 2, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Alan R. Katritzky,*a   Nader E. Abo-Dya,ab   Abdelmotaal Abdelmajeid,ac   Srinivasa R. Tala,a   M. S. Aminec  and  Said A. El-Fekyb  

* Corresponding authors

a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, USA
E-mail: katritzky@chem.ufl.edu
Fax: +1 352-392-9199
Tel: +1 352-392- 0554

b Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt

c Department of Chemistry, Faculty of Science, Benha University, Benha, Egypt

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.

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

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Article information

DOI
https://doi.org/10.1039/C0OB00663G
Article type
Paper
Submitted
03 Sep 2010
Accepted
21 Sep 2010
First published
10 Nov 2010

Org. Biomol. Chem., 2011,9, 596-599

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

A. R. Katritzky, N. E. Abo-Dya, A. Abdelmajeid, S. R. Tala, M. S. Amine and S. A. El-Feky, Org. Biomol. Chem., 2011, 9, 596 DOI: 10.1039/C0OB00663G

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