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Synthesis 2003(13): 2084-2088
DOI: 10.1055/s-2003-41053
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2,2- and 2,5-Disubstituted 1-Oxyl Pyrrolidine Radicals as New Homobifunctional Cross-Linking Spin Labels

Tamás Kálaia, József Jekőb, Wayne L. Hubbellc, Kálmán Hideg*a
a Institute of Organic and Medicinal Chemistry, University of Pécs, 7602 Pécs, P. O. Box 99, Hungary
Fax: +36(72)536219; e-Mail: kalman.hideg@aok.pte.hu;
b ICN Hungary Ltd., 4440 Tiszavasvári, P. O. Box 1, Hungary
c Jules Stein Eye Institute and Department of Chemistry and Biochemistry, UCLA, Los Angeles, CA 90095-7008, USA
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Publication History

Received 28 May 2003
Publication Date:
22 August 2003 (online)

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Abstract

The synthesis of 2,2- and 2,5-disubstituted pyrrolidine nitroxide radicals starting from readily available nitrones 1, 11 is described. The stable radicals are acylating (10, 20), alkylating (7, 17) and thiol-specific (8, 18) reagents capable of producing cross-links in proteins over distances in the range of 10-15 Å.

Key words

cross linking reagents - proteins - free radicals - Grignard reactions - nitrones - lithium