LNA (Locked Nucleic Acids): Synthesis of the adenine, cytosine, guanine, 5-methylcytosine, thymine and uracil bicyclonucleoside monomers, oligomerisation, and unprecedented nucleic acid recognition

Tetrahedron

Volumn 54, Issue 14, 1998, Pages 3607-3630

  Koshkin, Alexei A ^a   Singh, Sanjay K ^a   Nielsen, Poul ^b   Rajwanshi, Vivek K ^a   Kumar, Ravindra ^a   Meldgaard, Michael ^a   Olsen, Carl Erik ^c   Wengel, Jesper ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE;

ARTICLE; BASE PAIRING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEIC ACID SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; THERMOSTABILITY;

EID: 0032473890     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00094-5     Document Type: Article

References (30)

1. 1. Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 544.
2. 2. Beaucage, S. L.; Iyer, R P. Tetrahedron 1993, 49, 6123.
3. 3. Herdewijn, P. Liebigs Ann. 1996, 1337.
4. 4. Freier, S. M.; Altmann, K.-H. Nucleic Acids Res. 1997, 25, 4429.
5. 5. Hyrup, B.; Nielsen, P. E. Bioorg. Med. Chem. 1996, 4, 5.
6. 6. Nielsen, P. E.; Haaima, G. Chem. Soc. Rev. 1997, 73.
7. 7. Schultz, D. G., Gryaznov, S. M. Nucleic Acids Res. 1996, 24, 2966.
8. 8. Van Aerschot, A.; Verheggen, I.; Hendrix, C.; Herdewijn, P. Angew. Chem. Int. Ed. Engl. 1995, 34, 1338.
9. 9. Hendrix, C.; Rosemeyer, H.; Verheggen, I; Seela, F.; Van Aerschot, A.; Herdewijn, P. Chem. Eur. J. 1997, 3, 110.
10. 10. Egholm, M.; Buchardt, O.; Christensen, L.; Behrens, C.; Freier, S. M.; Driver, D. A.; Berg, R. H.; Kim, S. K.; Nordén, B.; Nielsen, P. E. Nature 1993, 365, 566.
11. 11. Nielsen, P.; Pfundheller, H. M.; Wengel, J. Chem. Commun. 1997, 825.
12. 12. Nielsen, P., Pfundheller, H. M.; Olsen, C. E.; Wengel, J. J. Chem. Soc. Perkin Trans. 1 1997, 3423.
13. 13. Bolli, M,.; Litten, J. C.; Schütz, R.; Leumann, C. J. Chem. Biol. 1996, 3, 197 and references cited therein.
14. 14. Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. J. Med. Chem. 1996, 39, 3739.
15. 15. Steffens, R.; Leumann, C. J. J. Am. Chem. Soc. 1997, 119, 11548.
16. 16. Obika, S.; Nanbu, D.; Hari, Y.; Morio, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735.
17. 17. Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, in press.
18. 18. Youssefyeh, R. D.; Verheyden, J. P. H.; Moffatt, J. G. J. Org. Chem. 1979, 44, 1301.
19. 19. Jones, G. H.; Taníguchi, M.; Tegg, D.; Moffatt, J. G. J. Org. Chem. 1979, 44, 1309.
20. 20. O-Yang, C.; Wu, H. Y.; Fraser-Smith, E. B.; Walker, K. A. M. Tetrahedron Lett. 1992, 33, 37.
21. 21. Thrane, H.; Fensholdt, J.; Regner, M.; Wengel, J. Tetrahedron, 1995, 51, 10389.
22. 22. Nielsen, K. D.; Kirpekar, F.; Roepstorff, P.; Wengel, J. Bioorg. Med. Chem. 1995, 3, 1493.
23. 23. Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
24. 24. Vorbrüggen, H.; Höfle, G. Chem. Ber. 1981, 114, 1256.
25. 25. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333.
26. 26. Obika, S.; Morio, K.; Nanbu, D.; Imanishi, T. Chem. Commun. 1997, 1643.
27. 27. Garner, P.; Ramakanth, S. J. Org. Chem. 1988, 53, 1294.
28. 28. Lin, T.-S.; Gao, Y.-S.; Mancini, W. R. J. Med. Chem. 1983, 26, 1691.
29. 29. Caruthers, M. H. Acc. Chem. Res. 1991, 24, 278.
30. 30. Waga, T.; Nishizaki, T.; Miyakawa, I.; Ohuri, H.; Meguro, H. Biosci. Biotech. Biochem. 1993, 57, 1433.