Synthesis of New Paramagnetic Fatty Acids and Lipophilic Spin Labels

Mária Balog; Christoph Abé; Tamás Kálai; Heinz-Jürgen Steinhoff; József Jekő; Kálmán Hideg

doi:10.1055/s-2007-966067

PAPER

Synthesis of New Paramagnetic Fatty Acids and Lipophilic Spin Labels

Mária Balog^a, Christoph Abé^b, Tamás Kálai^a, Heinz-Jürgen Steinhoff^b, József Jekő^c,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;

Abstract

All articles of this category

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.

Key words

fatty acids - free radicals - Grignard reaction - lipids - palladium-catalyzed reactions

Full Text

References

<A NAME="RP03807SS-1">1</A> Marsh D. Cevc G. Phospholipid Bilayers: Physical Principles and Models Wiley; Chichester: 1987.

<A NAME="RP03807SS-2">2</A> Hubbell WL. McConnell HM. J. Am. Chem. Soc. 1971, 93: 314

<A NAME="RP03807SS-3">3</A> Nusair NA. Tiburu EK. Dave PC. Lorigan GA. J. Magn. Reson. 2004, 168: 228

<A NAME="RP03807SS-4">4</A> Devaux PF. Fellmann P. Hervé P. Chem. Phys. Lipids 2002, 116: 115

<A NAME="RP03807SS-5A">5a</A> Griffith HO. Jost PC. In Spin Labeling Theory and Applications Berliner LJ. Academic Press Inc.; New York: 1976. p.453-523

<A NAME="RP03807SS-5B">5b</A> Hideg K. Hankovszky HO. In Biological Magnetic Resonance Vol. 8: Berliner LJ. Reuben J. Plenum Press; New York: 1989. p.427-488

<A NAME="RP03807SS-6A">6a</A> Mravljak J. Pecar S. Synth. Commun. 2004, 34: 3763

<A NAME="RP03807SS-6B">6b</A> Mravljak J. Zeisig R. Pecar S. J. Med. Chem. 2005, 48: 6393

<A NAME="RP03807SS-7">7</A> Zucker SD. Goessling W. Bootle EJ. Sterritt C. J. Lipid Res. 2001, 42: 1377

<A NAME="RP03807SS-8">8</A> Lozinsky E. Iametty S. Barbiroli A. Likhtenshtein GI. Kálai T. Hideg K. Bonomi F. Protein J. 2006, 25: 1

<A NAME="RP03807SS-9">9</A> Budai M. Reynaud-Angelin A. Szabó Z. Tóth S. Rontó G. Sage E. Gróf P. J. Photochem. Photobiol., B 2004, 77: 27

<A NAME="RP03807SS-10">10</A> Dhanesakaran A. Kotamraju S. Karunakaran C. Kalivendi SV. Thomas S. Kalyanaraman JJB. Free Radical Biol. Med. 2005, 39: 567

<A NAME="RP03807SS-11">11</A> Hideg K. Lex L. J. Chem. Soc., Chem. Commun. 1984, 1263

<A NAME="RP03807SS-12">12</A> Kálai T. Bárácz MN. Jerkovich G. Hankovszky HO. Hideg K. Synthesis 1995, 1278

<A NAME="RP03807SS-13">13</A> Keana JFW. In Spin Labeling II, Theory and Applications Berliner LJ. Academic Press; New York: 1979. p.115

<A NAME="RP03807SS-14A">14a</A> Hideg K. Lex L. J. Chem. Soc., Perkin Trans. 1 1986, 1431

<A NAME="RP03807SS-14B">14b</A> Rockenbauer A. Korecz L. Hideg K. J. Chem. Soc., Perkin Trans. 2 1993, 2149

<A NAME="RP03807SS-14C">14c</A> Kálai T. Jekõ J. Hubbell WL. Hideg K. Synthesis 2003, 2084

<A NAME="RP03807SS-15">15</A> Bárácz MN. Hankovszky HO. Sár PC. Jerkovich G. Hideg K. Synthesis 1996, 204

<A NAME="RP03807SS-16">16</A> Sár PC. Jekõ J. Fajer P. Hideg K. Synthesis 1999, 1039

<A NAME="RP03807SS-17">17</A> Chan K.-K. De Noble JP. Specian AC. Saucy G. J. Org. Chem. 1976, 41: 3497

<A NAME="RP03807SS-18">18</A> Hankovszky HO. Hideg K. Lex L. Synthesis 1980, 914

<A NAME="RP03807SS-19">19</A> Berliner LJ. Grünwald J. Hankovszky HO. Hideg K. Anal. Biochem. 1982, 119: 450

<A NAME="RP03807SS-20">20</A> Hideg K. Sár PC. Hideg K. Jerkovich G. Synthesis 1991, 616

<A NAME="RP03807SS-21">21</A> Belkin S. Mehlhorn RJ. Hideg K. Hankovszky HO. Packer L. Arch. Biochem. Biophys. 1987, 256: 232

<A NAME="RP03807SS-22">22</A> Murphy MP. Trends Biotech. Sci. 1997, 15: 326

<A NAME="RP03807SS-23">23</A> Hideg K. Hankovszky HO. Lex L. Kulcsár G. Synthesis 1980, 911

<A NAME="RP03807SS-24">24</A> Pearl IA. Org. Synth. Coll. Vol. IV Wiley; NewYork: 1963. p.972

<A NAME="RP03807SS-25">25</A> Rao CG. Org. Prep. Proced. Int. 1980, 12: 225

<A NAME="RP03807SS-26">26</A> Ashwood MS. Gibson AW. Houghton PG. Humprey GR. Roberts DC. Wright SHB. J. Chem. Soc., Perkin Trans. 1 1995, 641

<A NAME="RP03807SS-27">27</A> Underiner TL. Goering HL. J. Org. Chem. 1991, 56: 2563

<A NAME="RP03807SS-28A">28a</A> Chudinov AV. Rozantsev EG. Rosinov B. Izv. Akad. Nauk. Ser. Khim. 1983, 409 ; Chem. Abstr. 1983, 98, 197927

<A NAME="RP03807SS-28B">28b</A> Kálai T. Balog M. Jekõ J. Hideg K. Synthesis 1998, 1476

<A NAME="RP03807SS-29">29</A> Kálai T. Balog M. Jekõ J. Hubbell WL. Hideg K. Synthesis 2002, 2365

<A NAME="RP03807SS-30">30</A> Bellina F. Anselmi C. Rossi R. Tetrahedron Lett. 2001, 42: 3851

<A NAME="RP03807SS-31">31</A> Dalcanale E. Montanari F. J. Org. Chem. 1986, 51: 567

<A NAME="RP03807SS-32">32</A> Jost P. Libertini L. Hebert VC. Griffith OH. J. Mol. Biol. 1971, 59: 77

<A NAME="RP03807SS-33">33</A> Raju N. Spacek T. Jezek J. Caminiti IM. Leinisch F. Hideg K. Jezek P. Trommer WE. Appl. Magn. Reson. 2006, 30: 373

<A NAME="RP03807SS-34">34</A> Torssell K. Larsson ENV. Acta Chem. Scand. 1957, 11: 404