Synthesis of abasic locked nucleic acid and two seco-LNA derivatives and evaluation of their hybridization properties compared with their more flexible DNA counterparts

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5167-5176

  Kværnø, Lisbet ^a   Kumar, Ravindra ^a   Dahl, Britta M ^a   Olsen, Carl Erik ^b   Wengel, Jesper ^a,c  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

MONOMER; NUCLEIC ACID; NUCLEIC ACID BASE; OLIGORIBONUCLEOTIDE;

ARTICLE; CONFORMATIONAL TRANSITION; DNA DENATURATION; MOLECULAR HYBRIDIZATION; NUCLEIC ACID STRUCTURE; NUCLEOTIDE SEQUENCE; STRUCTURE ANALYSIS; SYNTHESIS;

BASE SEQUENCE; DNA; MAGNETIC RESONANCE SPECTROSCOPY; NUCLEIC ACID CONFORMATION; NUCLEIC ACID HYBRIDIZATION; NUCLEIC ACIDS;

EID: 0034714409     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000275x     Document Type: Article

References (37)

1. We have defined LNA as an oligonucleotide containing one or more 2′-O,4′-C-methylene-linked bicyclic ribonucleoside monomers.
2. L.
3. Vandendriessche, F.; Augustyns, K.; Van Aerschot, A.; Busson, R.; Hoogmartens, J.; Herdewijn, P. Tetrahedron 1993, 49, 7223.
4. Herdewijn, P. Liebigs Ann. Chem. 1996, 1337.
5. Kool, E. T. Chem. Rev. 1997, 97, 1473.
6. Tarkoy, M.; Bolli, M.; Leumann, C. Helv. Chim. Acta 1994, 77, 716.
7. Altmann, K. H.; Kesselring, R.; Francotte, E.; Rihs, G. Tetrahedron Lett. 1994, 35, 2331.
8. Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J. Y.; Wagner, R. W.; Matteucci, M. D. J. Med. Chem. 1996, 39, 3739.
9. Steffens, R.; Leumann, C. J. J. Am. Chem. Soc. 1997, 119, 11548.
10. Nielsen, P.; Pfundheller, H. M.; Olsen, C. E.; Wengel, J. J. Chem. Soc., Perkin Trans. 1 1997, 3423.
11. Christensen, N. K.; Petersen, M.; Nielsen, P.; Jacobsen, J. P.; Olsen, C. E.; Wengel, J. J. Am. Chem. Soc. 1998, 120, 5458.
12. Raunkjaer, M.; Wengel, J. J. Chem. Soc., Perkin Trans. 1 1999, 2543.
13. Wang, G. Y.; Gunic, E.; Girardet, J. L.; Stoisavljevic, V. Bioorg. Med. Chem. Lett. 1999, 9, 1147.
14. Wang, G. Y.; Girardet, J. L.; Gunic, E. Tetrahedron 1999, 55, 7707.
15. Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, 455.
16. Koshkin, A. A.; Singh, S. K.; Nielsen, P.; Rajwanshi, V. K.; Kumar, R.; Meldgaard, M.; Olsen, C. E.; Wengel, J. Tetrahedron 1998, 54, 3607.
17. Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Mono, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401.
18. Wengel, J.; Koshkin, A.; Singh, S. K.; Nielsen, P.; Meldgaard, M.; Rajwanshi, V. K.; Kumar, R.; Skouv, J.; Nielsen, C. B.; Jacobsen, J. P.; Jacobsen, N.; Olsen, C. E. Nucleosides Nucleotides 1999, 18, 1365.
19. Koshkin, A. A.; Nielsen, P.; Meldgaard, M.; Rajwanshi, V. K.; Singh, S. K.; Wengel, J. J. Am. Chem. Soc. 1998, 720, 13252.
20. Wengel, J. Acc. Chem. Res. 1999, 32, 301.
21. Plavec, J.; Thibaudeau, C.; Viswanadham, G.; Sund, C.; Chattopadhyaya, J. Chem. Commun. 1994, 781.
22. Plavec, J.; Thibaudeau, C.; Viswanadham, G.; Sund, C.; Sandstrom, A.; Chattopadhyaya, J. Tetrahedron 1995, 51, 11775.
23. Thibaudeau, C.; Chattopadhyaya, J. Nucleosides Nucleotides 1998, 17, 1589.
24. Obika, S.; Nanbu, D.; Hari, Y.; Mono, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735.
25. Bondesgaard, K.; Petersen, M.; Singh, S. K.; Rajwanshi, V. K.; Kumar, R.; Wengel, J.; Jacobsen, J. P. Chem. Eur. J., in press.
26. Nielsen, P.; Kirpekar, F.; Wengel, J. Nucleic Acids Res. 1994, 22, 703.
27. Nielsen, P.; Dreiøe, L. H.; Wengel, J. Biorg. Med. Chem. 1995, 3, 19.
28. Achter, E. K.; Felsenfield, G. Biopolymers 1971, 10, 1625.
29. Waga, T.; Nishizaki, T.; Miyakawa, I.; Ohrui, H.; Meguro, H. Biosci. Biotechnol. Biochem. 1993, 57, 1433.
30. Nielsen, P.; Wengel, J. Chem. Commun. 1998, 2645. No experimental data were included in this communication.
31. Caruthers, M. H. Acc. Chem. Res. 1991, 24, 278.
32. Dolan, S. C.; Macmillan: J. J. Chem. Soc., Chem. Commun. 1985, 1588.
33. m values were obtained as reported earlier. See ref 16.
34. Millican, T. A.; Chauncey, M. A.; Cutbush, S. D.; Eaton, M. A. W.; Gunning, J.; Mann, J.; Mock, G. A.; Neidle, S.; Patel, T. P. Nucleic Acids Res. 1984, 12, 7435.
35. Reduced binding affinities have also been observed for other ON analogues containing a flexible nucleobase on a rigified phosphor-diester backbone. (a) Marangoni, M.; Van Aershot, A.; Augustyns, P.; Rozenski, J.; Herdewijn, P. Nucleic Acids Res. 1997, 25, 3034.
36. (b) Epple, C.; Leumann, C. Chem. Biol. 1998, 5, 209.
37. Wincott, F.; Direnzo, A.; Shaffer, C.; Grimm, S.; Tracz, D.; Workman, C.; Sweedler, D.; Gonzalez, C.; Scaringe, S.; Usman, N. Nucleic Acids Res. 1995, 23, 2677.