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Synthesis 2010(17): 3021-3028  
DOI: 10.1055/s-0029-1218846
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Versatile Method of Tethering Biomolecules to Pyrrole Precursors for Functionalized Magnetic Polypyrrole Core-Shell Nanoparticles

Sebastian Karstena, Mohamed A. Ameena,b, Sabrina I. Kallänea, Alexandrina Nanc, Rodica Turcuc, Jürgen Liebscher*a
a Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany
Fax: +49(30)20937552; e-Mail: liebscher@chemie.hu-berlin.de;
b Department of Chemistry, Faculty of Science, El Minia University, El Minia 61519, Egypt
c National Institute of Research and Development for Isotopic and Molecular Technologies, Donath 65-103, 400293 Cluj-Napoca, Romania
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Publication History

Received 13 April 2010
Publication Date:
30 June 2010 (online)

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Abstract

A mild and versatile method based on copper-catalyzed [3+2] cycloaddition (Meldal-Sharpless reaction) was developed to tether biomolecules, such as monosaccharides, biotin, cholesterol, or uridine to the N-atom of pyrrole. The required azido and alkyne functions can be placed in either reactant, i.e. in the pyrrole or the biomolecule. The products are interesting precursors for functionalized superparamagnetic polypyrrole core-shell nanoparticles.

Key words

pyrroles - alkynes - azides - cycloaddition - biomolecules