High-affinity nucleic acid recognition using ‘LNA’ (locked nucleic acid, β-D-ribo configured LNA), ‘xylo-LNA’ (β-D-xylo configured LNA) or ‘α-L-LNA’ (α-L-ribo configured LNA)

(Note: The full text of this document is currently only available in the PDF Version )

Vivek K. Rajwanshi, Anders E. Håkansson, Ravindra Kumar and Jesper Wengel


Abstract

Remarkably strong binding affinities towards complementary single stranded DNA and RNA were obtained for 10- and 14-mer LNAs (locked nucleic acids) containing diastereoisomeric β-D-ribo, β-D-xylo or α-L-ribo configured LNA thymine monomers; a possible relevance of these results in relation to nucleic acid evolution is discussed.


References

  1. (a) M. Beier, F. Reck, T. Wagner, R. Krishnamurthy and A. Eschenmoser, Science, 1999, 283, 699 CrossRef CAS; (b) A. Eschenmoser, Science, 1999, 284, 2118 CrossRef CAS.
  2. G. W. Ashley, J. Am. Chem. Soc., 1992, 114, 9731 CrossRef CAS; S. Pitsch, Helv. Chim. Acta, 1997, 80, 2286 CrossRef CAS.
  3. (a) M. J. Damha, N. Usman and K. K. Ogilvie, Can. J. Chem., 1989, 67, 831 CAS; (b) J. M. L. Pieters, E. de Vroom, G. A. van der Marel, J. H. van Boom, T. M. G. Koning, R. Kaptein and C. Altona, Biochemistry, 1990, 29, 788 CrossRef CAS; (c) M. Resmini and W. Pfleiderer, Bioorg. Med. Chem. Lett., 1994, 4, 1909 CrossRef; (d) P. A. Giannaris and M. Damha, Can. J. Chem., 1994, 72, 909 CAS; (e) T. Mikita and G. P. Beardsley, Biochemistry, 1994, 33, 9195 CrossRef CAS; (f) M. J. Damha, C. J. Wilds, A. Noronha, I. Brukner, G. Borkow, D. Arion and M. A. Parniak, J. Am. Chem. Soc., 1998, 120, 12976 CrossRef CAS.
  4. (a) S. K. Singh, P. Nielsen, A. A. Koshkin and J. Wengel, Chem. Commun., 1998, 455 RSC; (b) A. A. Koshkin, S. K. Singh, P. Nielsen, V. K. Rajwanshi, R. Kumar, M. Meldgaard, C. E. Olsen and J. Wengel, Tetrahedron, 1998, 54, 3607 CrossRef CAS; (c) S. K. Singh and J. Wengel, Chem. Commun., 1998, 1247 RSC; (d) A. A. Koshkin, P. Nielsen, M. Meldgaard, V. K. Rajwanshi, S. K. Singh and J. Wengel, J. Am. Chem. Soc., 1998, 120, 13252 CrossRef CAS; (e) S. Obika, D. Nanbu, Y. Hari, J. Andoh, K. Morio, T. Doi and T. Imanishi, Tetrahedron Lett., 1998, 39, 5401 CrossRef CAS; (f) J. Wengel, Acc. Chem. Res., 1999, 32, 301 CrossRef CAS.
  5. V. K. Rajwanshi, A. E. Håkansson, B. M. Dahl and J. Wengel, Chem. Commun., 1999, 1395 RSC.
  6. M. H. Caruthers, Acc. Chem. Res., 1991, 24, 278 CrossRef CAS.
  7. D. G. Schultz and S. M. Gryaznov, Nucleic Acids Res., 1996, 24, 2966 CrossRef CAS.
  8. C. Hendrix, H. Rosemeyer, I. Verheggen, F. Seela, A. Van Aerschot and P. Herdewijn, Chem. Eur. J., 1997, 3, 110 CrossRef CAS; C. Hendrix, H. Rosemeyer, B. De Bouvere, A. Van Aerschot, F. Seela and P. Herdewijn, Chem. Eur. J., 1997, 3, 1513 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.