Synthesis 2007(11): 1663-1670  
DOI: 10.1055/s-2007-966067
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of New Paramagnetic Fatty Acids and Lipophilic Spin Labels

Mária Baloga, Christoph Abéb, Tamás Kálaia, Heinz-Jürgen Steinhoffb, József Jekőc,d, Kálmán Hideg*a
a Department of Organic and Medicinal Chemistry, University of Pécs, P.O. Box 99, 7602 Pécs, Hungary
b Department of Physics, University of Osnabrück, Barbara Str. 7, 49069 Osnabrück, Germany
c ICN Hungary, P.O. Box 1, 4440 Tiszavasvári, Hungary
d Department of Chemistry, College of Nyíregyháza, Sóstói st. 31/B, 4440 Nyíregyháza, Hungary
Fax: +36(72)536219; e-Mail: kalman.hideg@aok.pte.hu;
Further Information

Publication History

Received 28 March 2007
Publication Date:
11 May 2007 (eFirst)

Abstract

Starting from readily available five-membered cyclic nitrones, paramagnetic analogues of palmitic and hexadec-2E-enoic acids are described with a range of pyrrolidine ring orientations. Herein we report the synthesis of 3,4-disubstituted lipophilic pyrroline nitroxides through a palladium-catalyzed cross-coupling reaction. Lipophilic phosphonium salt and SH-specific labels (methanethiosulfonates and isoselenuronium salts) with allylic and propargylic terminal groups are also described.

    References

  • 1 Marsh D. Cevc G. Phospholipid Bilayers: Physical Principles and Models   Wiley; Chichester: 1987. 
  • 2 Hubbell WL. McConnell HM. J. Am. Chem. Soc.  1971,  93:  314 
  • 3 Nusair NA. Tiburu EK. Dave PC. Lorigan GA. J. Magn. Reson.  2004,  168:  228 
  • 4 Devaux PF. Fellmann P. Hervé P. Chem. Phys. Lipids  2002,  116:  115 
  • 5a Griffith HO. Jost PC. In Spin Labeling Theory and Applications   Berliner LJ. Academic Press Inc.; New York: 1976.  p.453-523  
  • 5b Hideg K. Hankovszky HO. In Biological Magnetic Resonance   Vol. 8:  Berliner LJ. Reuben J. Plenum Press; New York: 1989.  p.427-488  
  • 6a Mravljak J. Pecar S. Synth. Commun.  2004,  34:  3763 
  • 6b Mravljak J. Zeisig R. Pecar S. J. Med. Chem.  2005,  48:  6393 
  • 7 Zucker SD. Goessling W. Bootle EJ. Sterritt C. J. Lipid Res.  2001,  42:  1377 
  • 8 Lozinsky E. Iametty S. Barbiroli A. Likhtenshtein GI. Kálai T. Hideg K. Bonomi F. Protein J.  2006,  25: 
  • 9 Budai M. Reynaud-Angelin A. Szabó Z. Tóth S. Rontó G. Sage E. Gróf P. J. Photochem. Photobiol., B  2004,  77:  27 
  • 10 Dhanesakaran A. Kotamraju S. Karunakaran C. Kalivendi SV. Thomas S. Kalyanaraman JJB. Free Radical Biol. Med.  2005,  39:  567 
  • 11 Hideg K. Lex L. J. Chem. Soc., Chem. Commun.  1984,  1263 
  • 12 Kálai T. Bárácz MN. Jerkovich G. Hankovszky HO. Hideg K. Synthesis  1995,  1278 
  • 13 Keana JFW. In Spin Labeling II, Theory and Applications   Berliner LJ. Academic Press; New York: 1979.  p.115 
  • 14a Hideg K. Lex L. J. Chem. Soc., Perkin Trans. 1  1986,  1431 
  • 14b Rockenbauer A. Korecz L. Hideg K. J. Chem. Soc., Perkin Trans. 2  1993,  2149 
  • 14c Kálai T. Jekõ J. Hubbell WL. Hideg K. Synthesis  2003,  2084 
  • 15 Bárácz MN. Hankovszky HO. Sár PC. Jerkovich G. Hideg K. Synthesis  1996,  204 
  • 16 Sár PC. Jekõ J. Fajer P. Hideg K. Synthesis  1999,  1039 
  • 17 Chan K.-K. De Noble JP. Specian AC. Saucy G. J. Org. Chem.  1976,  41:  3497 
  • 18 Hankovszky HO. Hideg K. Lex L. Synthesis  1980,  914 
  • 19 Berliner LJ. Grünwald J. Hankovszky HO. Hideg K. Anal. Biochem.  1982,  119:  450 
  • 20 Hideg K. Sár PC. Hideg K. Jerkovich G. Synthesis  1991,  616 
  • 21 Belkin S. Mehlhorn RJ. Hideg K. Hankovszky HO. Packer L. Arch. Biochem. Biophys.  1987,  256:  232 
  • 22 Murphy MP. Trends Biotech. Sci.  1997,  15:  326 
  • 23 Hideg K. Hankovszky HO. Lex L. Kulcsár G. Synthesis  1980,  911 
  • 24 Pearl IA. Org. Synth. Coll. Vol. IV   Wiley; NewYork: 1963.  p.972 
  • 25 Rao CG. Org. Prep. Proced. Int.  1980,  12:  225 
  • 26 Ashwood MS. Gibson AW. Houghton PG. Humprey GR. Roberts DC. Wright SHB. J. Chem. Soc., Perkin Trans. 1  1995,  641 
  • 27 Underiner TL. Goering HL. J. Org. Chem.  1991,  56:  2563 
  • 28a Chudinov AV. Rozantsev EG. Rosinov B. Izv. Akad. Nauk. Ser. Khim.  1983,  409 ; Chem. Abstr. 1983, 98, 197927
  • 28b Kálai T. Balog M. Jekõ J. Hideg K. Synthesis  1998,  1476 
  • 29 Kálai T. Balog M. Jekõ J. Hubbell WL. Hideg K. Synthesis  2002,  2365 
  • 30 Bellina F. Anselmi C. Rossi R. Tetrahedron Lett.  2001,  42:  3851 
  • 31 Dalcanale E. Montanari F. J. Org. Chem.  1986,  51:  567 
  • 32 Jost P. Libertini L. Hebert VC. Griffith OH. J. Mol. Biol.  1971,  59:  77 
  • 33 Raju N. Spacek T. Jezek J. Caminiti IM. Leinisch F. Hideg K. Jezek P. Trommer WE. Appl. Magn. Reson.  2006,  30:  373 
  • 34 Torssell K. Larsson ENV. Acta Chem. Scand.  1957,  11:  404