PDF herunterladen
Synthesis 2010(21): 3710-3714  
DOI: 10.1055/s-0030-1258243
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Readily Accessible Triazole-Linked Dimer Deoxynucleoside Phosphoramidite for Solid-Phase Oligonucleotide Synthesis

Srivari Chandrasekhar*a, Pabbaraja Sriharia, Chidalla Nagesha, Nayani Kiranmaia, Narayana Nageshb, M. Mohammed Idris*b
a Organic Chemistry Division - I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: srivaric@iict.res.in;
b Centre for Cellular and Molecular Biology, Hyderabad 500 007, India
e-Mail: idris@ccmb.res.in.;
Weitere Informationen

Publikationsverlauf

Received 25 June 2010
Publikationsdatum:
07. September 2010 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A concise preparation of triazole-linked deoxynucleoside phosphoramidite for its direct use in solid-phase oligonucleo­tide synthesis is reported. This dimer has successfully been utilized in solid-phase synthesis to make the 10- and 12-mer oligomers.

Key words

nucleotides - triazole - click - oligomer - solid-phase synthesis

    References

  • 1a Koropatnick J. Berg RW. Jason TLH. Recent Development in Gene Therapy   1st ed.:  Transworld Research Network; Trivandrum: 2007.  p.151-180  
    Google Scholar
  • 1b Haas J. Engels JW. Tetrahedron Lett.  2007,  48:  8891 
    Google Scholar
  • 1c Buchini S. Leumann CJ. Curr. Opin. Chem. Biol.  2003,  7:  717 
    Google Scholar
  • 1d Kurreck J. Eur. J. Biochem.  2003,  270:  1628 
    Google Scholar
  • 2a For more recent papers on these derivatives see: Olesiak M. Stec WJ. Okruszek A. Org. Biomol. Chem.  2009,  7:  2162 ; and references cited therein
    Google Scholar
  • 2b Kanaori K. Tamura Y. Wada T. Nishi M. Kanehara H. Morii T. Tajima K. Makino K. Biochemistry  1999,  38:  16058 
    Google Scholar
  • 2c De Mesmaeker A. Altmann KH. Waldner A. Wendeborn S. Curr. Opin. Struct. Biol.  1995,  5:  343 
    Google Scholar
  • 2d Uhlmann E. Peyman A. Chem. Rev.  1990,  90:  543 
    Google Scholar
  • 2e Brill WK.-D. Nielsen J. Carruthers MH. Tetrahedron Lett.  1988,  29:  5517 
    Google Scholar
  • 3a Li P. Sergueeva ZA. Dobrikov M. Shaw BR. Chem. Rev.  2007,  107:  4746 
    Google Scholar
  • 3b Higashida R. Oka N. Kawanaka T. Wada T. Chem. Commun.  2009,  2466 
    Google Scholar
  • 3c For other derivatives including boronates, see: Han Q. Sarafianos SG. Arnold E. Parniak MA. Gaffney BL. Jones RA. Tetrahedron  2009,  65:  7915 
    Google Scholar
  • 4a Nina M. Fonne-Pfister R. Beaudegnies R. Chekatt H. Jung PMJ. Murphy-Kessabi F. de Mesmaeker A. Wendeborn S. J. Am. Chem. Soc.  2005,  127:  6027 
    Google Scholar
  • 4b de Mesmaeker A. Lebreton J. Waldner A. Fritsch V. Wolf RM. Bioorg. Med. Chem. Lett.  1994,  4:  873 
    Google Scholar
  • 5a Viswanadham G. Petersen GV. Wengel J. Bioorg. Med. Chem. Lett.  1996,  6:  987 
    Google Scholar
  • 5b Petersen GV. Wengel J. Tetrahedron  1995,  51:  2145 
    Google Scholar
  • 6a Matt PV. Lochmann T. Altmann K.-H. Bioorg. Med. Chem. Lett.  1997,  7:  1549 
    Google Scholar
  • 6b Matt PV. Altmann K.-H. Bioorg. Med. Chem. Lett.  1997,  7:  1553 
    Google Scholar
  • 6c Filichev VV. Malin AA. Ostrovskii VA. Pedersen EB. Helv. Chim. Acta  2002,  85:  2847 
    Google Scholar
  • 7 Isobe H. Fujino T. Yamazaki N. Guillot-Nieckowski M. Nakamura E. Org. Lett.  2008,  10:  3729 
    CrossrefPubMedGoogle Scholar
  • For few recent publications, see:
  • 8a Koissi N. Lonnberg H. Nucleosides, Nucleotides, Nucleic Acids  2007,  26:  1203 
    Google Scholar
  • 8b Krueger AT. Lu H. Lee AHF. Kool ET. Acc. Chem. Res.  2007,  40:  141 
    Google Scholar
  • 8c Liu H. Gao J. Kool ET. J. Am. Chem. Soc.  2005,  127:  1396 
    Google Scholar
  • 8d Kool ET. Acc. Chem. Res.  2002,  35:  936 
    Google Scholar
  • For few recent sugar modified nucleosides, see:
  • 9a Stauffiger A. Leumann CJ. Eur. J. Org. Chem.  2009,  1153 
    Google Scholar
  • 9b Prakash TP. Bhat B. Curr. Top. Med. Chem.  2007,  7:  641 
    Google Scholar
  • 9c Gagneron J. Gosselin G. Mathe C. Eur. J. Org. Chem.  2006,  4891 
    Google Scholar
  • 9d Prakash TP. Kawasaki AM. Lesnik EA. Owens SR. Manoharan M. Org. Lett.  2003,  5:  403 
    Google Scholar
  • 10a Nielsen PE. Pure Appl. Chem.  1998,  70:  105 
    Google Scholar
  • 10b Fujii M. Yoshida K. Hidaka J. Ohtsu T. Bioorg. Med. Chem. Lett.  1997,  7:  637 
    Google Scholar
  • 11a Zhang N. Tan C. Cai P. Zhang P. Zhao Y. Jiang Y. Bioorg. Med. Chem.  2009,  17:  2441 
    Google Scholar
  • 11b Summerton J. Weller D. Nucleosides Nucleotides  1997,  16:  889 
    Google Scholar
  • 12 For a recent review, see: Amblard F. Cho JH. Schinazi RF. Chem. Rev.  2009,  109:  4207 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • 13 Chandrasekhar S. Basu D. Rambabu Ch. Tetrahedron Lett.  2006,  47:  3059 
    CrossrefGoogle Scholar
  • 14 Srihari P. Dutta P. Srinivasa Rao R. Yadav JS. Chandrasekhar S. Thombare P. Mohapatra J. Chatterjee A. Jain MR. Bioorg. Med. Chem.  2009,  19:  5569 
    CrossrefGoogle Scholar
  • For other contributions on click chemistry from our group, see:
  • 15a Chandrasekhar S. Lohitha Rao Ch. Nagesh Ch. Raji Reddy Ch. Sridhar B. Tetrahedron Lett.  2007,  48:  5869 
    Google Scholar
  • 15b Chandrasekhar S. Tiwari B. Parida BB. Raji Reddy Ch. Tetrahedron: Asymmetry  2008,  19:  495 
    Google Scholar
  • 15c Chandrasekhar S. Seenaiah M. Lohitha Rao Ch. Raji Reddy Ch. Tetrahedron  2008,  64:  11325 
    Google Scholar
  • 16a Lazrek HB. Rochdi A. Engels JW. Nucleosides Nucleotides  1999,  18:  1257 
    Google Scholar
  • For recent papers with triazoles, see:
  • 16b Nuzzi A. Massi A. Dondoni A. QSAR Comb. Sci.  2007,  26:  1191 
    Google Scholar
  • 16c Lucas R. Neto V. Hadj Bouazza A. Zerrouki R. Granet R. Krausz Champavier Y. Tetrahedron Lett.  2008,  49:  1004 
    Google Scholar
  • 16d Lucas R. Zerrouki R. Granet R. Champavier YK. Tetrahedron  2008,  64:  5467 
    Google Scholar
  • 16e Isobe H. Fujino T. Yamazaki N. Tetrahedron Lett.  2009,  50:  4101 ; and references cited therein
    Google Scholar
  • 16f El-Sagheer AH. Brown T. J. Am. Chem. Soc.  2009,  131:  3958 
    Google Scholar
  • 17 Chandrasekhar S. Rambabu Ch. Syamprasad Reddy A. Org. Lett.  2008,  10:  4355 
    CrossrefPubMedGoogle Scholar
  • 18a Corey EJ. Fuchs PL. Tetrahedron Lett.  1972,  13:  3769 
    Google Scholar
  • 18b Takahashi S. Nakata T. J. Org. Chem.  2002,  67:  5739 
    Google Scholar
19

Initially, the reaction was tried with n-BuLi and the yield was found to be poor as the reaction ended with an intractable mixture of products.