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Synlett 2009(7): 1023-1033  
DOI: 10.1055/s-0028-1088148
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Recognition in Biomembrane Models: What is behind a ‘Simple Model’

Stefano Boroccia, Francesca Ceccaccib, Oscar Crucianic, Giovanna Mancini*c, Alessandro Sorrentic
a Dipartimento di Scienze Ambientali, Università della Tuscia, Largo dell’Università, 01100 Viterbo, Italy
b Dipartimento di Chimica, Università degli Studi di Roma ‘La Sapienza’, P. le Aldo Moro 5, 00185 Roma, Italy
c CNR, Istituto di Metodologie Chimiche, Dipartimento di Chimica, Università degli Studi di Roma ‘La Sapienza’, P. le Aldo Moro 5, 00185 Roma, Italy
Fax: +39(06)490421; e-Mail: giovanna.mancini@uniroma1.it;
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Publication History

Received 2 October 2008
Publication Date:
20 March 2009 (online)

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Abstract

The investigation of chiral recognition in micelles and liposomes used as biomembrane models relies, in principle, on physicochemical tools, such as circular dichroism, NMR spectroscopy, and theoretical calculations. However, the need for proper model aggregates and suitable markers of chirality has prompted us to face some organic synthesis exercises with problems that synthetic chemists usually find with much more complex syntheses. Our synthetic efforts were compensated by the results we got in the successive physicochemical investigations.

1 Introduction

2 The Chirality Markers

3 The Amphiphilic Components and the Models

4 The Tools: Some Brief Remarks

5 After All the Work: The Results

6 Concluding Remarks

Key words

chiral recognition - deracemization - aggregates - amphiphiles - chirality markers

    References

  • 1 Morrison RT. Boyd RN. In Organic Chemistry   3rd ed.:  Allyn and Bacon; Boston: 1978.  p.122 
    Google Scholar
  • 2 Lehn J.-M. Angew. Chem., Int. Ed. Engl.  1988,  27:  89 
    CrossrefGoogle Scholar
  • 3a Menger FM. Angelova MI. Acc. Chem. Res.  1998,  31:  789 
    Google Scholar
  • 3b Menger FM. Chlebowski ME. Galloway AL. Lu H. Seredyuk VA. Sorrells JL. Zhang H. Langmuir  2005,  21:  10336 
    Google Scholar
  • 4 Morigaki K. Dallavalle S. Walde P. Colonna S. Luisi PL. J. Am. Chem. Soc.  1997,  119:  292 
    CrossrefGoogle Scholar
  • 5 Arnett EM. Chao J. Kinzig BJ. Stewart MV. Thompson O. Verbiar RJ. J. Am. Chem. Soc.  1982,  104:  389 
    CrossrefGoogle Scholar
  • 6 Vollhardt D. Emrich G. Gutberlet T. Fuhrhop J.-H. Langmuir  1996,  12:  5659 
    CrossrefGoogle Scholar
  • 7 Weissbuch I. Berfeld M. Bouwman W. Kjaer K. Als-Nielsen J. Lahav M. Laiserowitz L. J. Am. Chem. Soc.  1997,  119:  933 
    CrossrefGoogle Scholar
  • 8 Arnett EM. Thompson O. J. Am. Chem. Soc.  1981,  103:  968 
    CrossrefGoogle Scholar
  • 9 Weissbuch I. Bolbach G. Zepik H. Shavit E. Tang M. Frey J. Jensen TR. Kjaer K. Leiserowitz L. Lahav M. J. Am. Chem. Soc.  2002,  124:  9093 
    CrossrefPubMedGoogle Scholar
  • 10 Lalitha S. Kumar AS. Stine KJ. Covey DF. J. Supramol. Chem.  2001,  1:  53 
    Google Scholar
  • 11 Arnett EM. Gold JM. J. Am. Chem. Soc.  1982,  104:  636 
    CrossrefGoogle Scholar
  • 12 Pathirana S. Neely WC. Myers LJ. Vodyanoy V. J. Am. Chem. Soc.  1992,  114:  1404 
    Google Scholar
  • 13 Nakagawa H. Onoda M. Masuoka Y. Yamada K.-I. Chirality  2006,  18:  212 
    CrossrefGoogle Scholar
  • 14 Fadok VA. de Cathelineau A. Daleke DL. Henson PH. Bratton DL. J. Biol. Chem.  2001,  276:  1071 
    CrossrefGoogle Scholar
  • 15 Addona GH. Sandermann H. Kloczewiak MA. Miller KW. Biochim. Biophys. Acta  2003,  1609:  177 
    Google Scholar
  • 16 Suchyna TM. Tape SE. Koeppe RE. Andersen OS. Sachs F. Gottlieb PA. Nature (London)  2004,  430:  235 
    CrossrefGoogle Scholar
  • 17 Li CC. Adams R. J. Am. Chem. Soc.  1935,  57:  1565 ; and references cited therein
    CrossrefGoogle Scholar
  • 18 Fanta PE. Chem. Rev.  1964,  64:  613 
    CrossrefGoogle Scholar
  • 19 Bella J. Borocci S. Mancini G. Langmuir  1999,  15:  8025 
    CrossrefGoogle Scholar
  • 20a Andreani R. Bombelli C. Borocci S. Lah J. Mancini G. Mencarelli P. Vesnaver G. Villani C. Tetrahedron: Asymmetry  2004,  15:  987 
    Google Scholar
  • 20b Ceccacci F. Giansanti L. Mancini G. Mencarelli P. Sorrenti A. New J. Chem.  2007,  31:  86 
    Google Scholar
  • 21a Miyaura N. Yanagi T. Suzuki A. Synth. Commun.  1981,  11:  513 
    Google Scholar
  • 21b Weissmann H. Milstein D. Chem. Commun.  1999,  1901 
    Google Scholar
  • 22 Belogi G. Croce M. Mancini G. Langmuir  1997,  13:  2903 
    CrossrefGoogle Scholar
  • 23 Bombelli C. Borocci S. Lupi F. Mancini G. Mannina L. Segre AL. Viel S. J. Am. Chem. Soc.  2004,  126:  13354 
    CrossrefGoogle Scholar
  • 24a Bombelli C. Bernardini C. Elemento G. Mancini G. Sorrenti A. Villani C. J. Am. Chem. Soc.  2008,  130:  2732 
    Google Scholar
  • 24b Ceccacci F. Giansanti L. Levi Mortera S. Mancini G. Sorrenti A. Villani C. Bioorg. Chem.  2008,  36:  252 
    Google Scholar
  • 25a Vásquez J. Garcia-Calvo M. Valdivieso F. Mayor F. Mayor F. J. Biol. Chem.  1998,  263:  1255 
    Google Scholar
  • 25b Rodrigues CMP. Solá S. Castro RE. Laires P. Brites D. Moura JJG. J. Lipid Res.  2002,  43:  885 
    Google Scholar
  • 26a Borocci S. Erba M. Mancini G. Scipioni A. Langmuir  1998,  14:  1960 
    Google Scholar
  • 26b Borocci S. Ceccacci F. Galantini L. Mancini G. Monti D. Scipioni A. Venanzi M. Chirality  2003,  15:  441 
    Google Scholar
  • 26c Ceccacci F. Mancini G. Sferrazza A. Villani C. J. Am. Chem. Soc.  2005,  127:  13762 
    Google Scholar
  • 26d Alzalamira A. Ceccacci F. Monti D. Levi Mortera S. Mancini G. Sorrenti A. Venanzi M. Villani C. Tetrahedron: Asymmetry  2007,  18:  1868 
    Google Scholar
  • 26e Bombelli C. Borocci S. Cruciani O. Mancini G. Monti D. Segre AL. Sorrenti A. Venanzi M. Tetrahedron: Asymmetry  2008,  19:  124 
    Google Scholar
  • 27 Cruciani O. Borocci S. La Manna R. Mancini G. Segre AL. Tetrahedron: Asymmetry  2006,  17:  2731 
    CrossrefGoogle Scholar
  • 28a Stÿver HD. Fraechet JMJ. Macromolecules  1991,  24:  883 
    Google Scholar
  • 28b Gross JD. Costa PR. Dubacq JB. Warschawski DE. Lirsca PN. Devaux PF. Griffin RG. J. Magn. Reson.  1995,  106:  187 
    Google Scholar
  • 28c Cheng LL. Lean CL. Bogdanova A. Wright SC. Ackerman JL. Brady TJ. Garrido L. Magn. Reson. Med.  1996,  36:  653 
    Google Scholar
  • 28d Anderson RC. Jarema MA. Shapiro MJ. Stokes JP. Ziliox M. J. Org. Chem.  1995,  60:  2650 
    Google Scholar
  • 28e Keifer P. Baltusis L. Rice DM. Tymiak A. Shoolery JN. J. Magn. Reson.  1996,  A119:  65 
    Google Scholar
  • 28f Deshmukh AP. Simpson AJ. Hatcher PG. Phytochemistry  2003,  64:  1163 
    Google Scholar
  • 29 Cruciani O. Mannina L. Sobolev AP. Cametti C. Segre AL. Molecules  2006,  11:  334 
    CrossrefGoogle Scholar
  • 30 Long JR. Sun BQ. Bowen A. Griffin RG. J. Am. Chem. Soc.  1994,  116:  11950 
    CrossrefGoogle Scholar
  • 31a Allenmark S. Chirality  2003,  15:  409 ; and references cited therein
    Google Scholar
  • 31b Berova N. Di Bari L. Piscitelli G. Chem. Soc. Rev.  2007,  36:  914 
    Google Scholar
  • 32 Zsila F. Bikadi Z. Fitos I. Simony M. Curr. Drug Discovery Technol.  2004,  1:  133 
    CrossrefGoogle Scholar
  • 33 Ceccacci F. Diociaiuti M. Galantini L. Mancini G. Mencarelli P. Scipioni A. Villani C. Org. Lett.  2004,  6:  1565 
    CrossrefGoogle Scholar
  • 34 van Gunsteren WF. Berendsen HCJ. Angew. Chem. Int. Ed. Engl.  1990,  29:  992 
    Google Scholar
  • 35 Tessmer MR. Meyer J.-P. Hruby VJ. Kallick DA. J. Med. Chem.  1997,  40:  2148 
    Google Scholar
  • 36a Wilkes BC. Schiller PW. Biopolymers  1994,  34:  1213 
    Google Scholar
  • 36b Carpenter KA. Wilkes BC. Weltrowska G. Schiller PW. Eur. J. Biochem.  1996,  241:  756 
    Google Scholar
  • 37 Kloosterman DA. Goodwin JT. Burton PS. Conradi RA. Stockman BJ. Scahill TA. Blinn JR. Biopolymers  2000,  53:  396 
    CrossrefGoogle Scholar
  • 38a Cerichelli G. Luchetti L. Mancini G. Langmuir  1997,  13:  4767 
    Google Scholar
  • 38b Borocci S. Mancini G. Cerichelli G. Luchetti L. Langmuir  1999,  15:  2627 
    Google Scholar
  • 39 Ceccacci F. Cruciani O. Diociaiuti M. Formisano G. Galantini L. Lindner W. Mancini G. Villani C. Tetrahedron: Asymmetry  2006,  17:  1603 
    CrossrefGoogle Scholar
  • 40a Lightner DA. Gawromski JK. Gawromska K. J. Am. Chem. Soc.  1985,  107:  2456 
    Google Scholar
  • 40b Lightner DA. Gawromski JK. Wijekoon WMD. J. Am. Chem. Soc.  1987,  109:  6354 
    Google Scholar