Download PDF
Synthesis 2012(4): 648-652  
DOI: 10.1055/s-0031-1289672
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Benzophenone C-Nucleoside as Potential Triplet Energy and Charge Donor in Nucleic Acids

Michael Weinberger, Hans-Achim Wagenknecht*
Institute for Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)60844825; e-Mail: wagenknecht@kit.edu;
Further Information

Publication History

Received 8 November 2011
Publication Date:
23 January 2012 (online)

    Permissions and Reprints All articles of this category

Abstract

A synthetic route to the C-nucleoside that bears benzophenone as a DNA base substitution directly at the anomeric center of the 2′-deoxyribofuranoside was worked out. Furthermore, the α-anomer of this artificial nucleoside was converted synthetically into the corresponding DNA building block and incorporated into two representative oligonucleotides by automated phosphoramidite chemistry. The chromophore-modified DNA was characterized by methods of optical spectroscopy. The absorption band at ∼350 nm can be used for selective excitation of the benzophenone chromophore outside the nucleic acid absorption range, which makes the benzophenone nucleoside potentially useful for photochemical and photobiological applications.

Key words

DNA - oligonucleotide - phosphorescence - photocatalysis - sensitizer

    References

  • 1 See review: Fleming SA. Tetrahedron  1995,  51:  12479 
    Google Scholar
  • 2 See review: Dormán G. Prestwich GD. Biochemistry  1994,  33:  5661 
    Google Scholar
  • 3 Galardy RE. Craig LC. Jamieson JD. Printz MP. J. Biol. Chem.  1974,  249:  3510 
    Google Scholar
  • See reviews:
  • 4a Fagnoni M. Dondi D. Ravelli D. Albini A. Chem. Rev.  2007,  107:  2725 
    Google Scholar
  • 4b Ravelli D. Dondi D. Fagnoni M. Albini A. Chem. Soc. Rev.  2009,  38:  1999 
    Google Scholar
  • See reviews:
  • 5a Svoboda J. König B. Chem. Rev.  2006,  106:  5413 
    Google Scholar
  • 5b Wessig P. Angew. Chem. Int. Ed.  2006,  45:  2168 
    Google Scholar
  • 6a Müller C. Bauer A. Bach T. Angew. Chem. Int. Ed.  2009,  48:  6640 
    Google Scholar
  • 6b Müller C. Bauer A. Maturi MM. Cuquerella MC. Miranda MA. Bach T. J. Am. Chem. Soc.  2011,  133:  16689 
    Google Scholar
  • 7 Kauble DF. Lynch V. Krische MJ. J. Org. Chem.  2003,  68:  15 
    Google Scholar
  • 8 Bauer A. Westkämper F. Grimme S. Bach T. Nature  2005,  436:  1139 
    Google Scholar
  • 9a Lehmann TE. Berkessel A. J. Org. Chem.  1997,  62:  302 
    Google Scholar
  • 9b Lehmann TE. Müller G. Berkessel A. J. Org. Chem.  2000,  65:  2508 
    Google Scholar
  • 10 Paris C. Encinas S. Belmadoui N. Climent MJ. Miranda MA. Org. Lett.  2008,  10:  4409 
    Google Scholar
  • 11 Musier-Forsyth K. Schimmel P. Biochemistry  1994,  33:  773 
    Google Scholar
  • 12 Nakatani K. Yoshida T. Saito I. J. Am. Chem. Soc.  2002,  124:  2118 
    Google Scholar
  • 13 Nakatani K. Saito I. Top. Curr. Chem.  2004,  236:  163 
    Google Scholar
  • 14a Hoffer M. Chem. Ber.  1960,  93:  2777 
    Google Scholar
  • 14b Rolland V. Kotera M. Lhomme J. Synth. Commun.  1997,  27:  3505 
    Google Scholar
  • 14c Dhimitruka I. SantaLucia J. Synlett  2004,  335 
    Google Scholar
  • 14d Chin T.-M. Huang L.-K. Kan L.-S. J. Chin. Chem. Soc.  1997,  44:  413 
    Google Scholar
  • 15 Štambaský J. Hocek M. Kočovský P. Chem. Rev.  2009,  109:  6729 
    Google Scholar
  • 16 Mirjalili BF. Zolfigol MA. Bamoniri A. Hazar A. Bull. Korean Chem. Soc.  2004,  25:  1075 
    Google Scholar
  • 17 Adam W. Arnold MA. Nau WM. Pischel U. Saha-Möller CR. J. Am. Chem. Soc.  2002,  124:  3893 
    Google Scholar
  • 18a Douki T. Cadet J. Int. J. Radiat. Biol.  1999,  75:  571 
    Google Scholar
  • 18b Morin B. Cadet J. Photochem. Photobiol.  1994,  60:  102 
    Google Scholar
  • 19 Delatour T. Douki T. D’Ham C. Cadet J. Photochem. Photobiol.  1998,  44:  191 
    Google Scholar
  • 20 Hélène C. Charlier M. Biochimie  1971,  53:  1175 
    Google Scholar
  • 21 Lamola AA. J. Am. Chem. Soc.  1966,  88:  813 
    Google Scholar
  • 22 Jennings BH. Pastra S.-C. Wellington JL. Photochem. Photobiol.  1970,  11:  215 
    Google Scholar