LNA guanine and 2,6-diaminopurine. Synthesis, characterization and hybridization properties of LNA 2,6-diaminopurine containing oligonucleotides

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 9, 2004, Pages 2385-2396

  Rosenbohm, Christoph ^a   Pedersen, Daniel Sejer ^a,c   Frieden, Miriam ^a   Jensen, Flemming R ^a   Arent, Susan ^b   Larsen, Sine ^b   Koch, Troels ^a  

^a Santaris Pharma AS   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Antisense agents; Bioorganic chemistry; Nucleosides; Oligonucleotides

Indexed keywords

2,6 DIAMINOPURINE DERIVATIVE; ANTISENSE OLIGODEOXYNUCLEOTIDE; COMPLEMENTARY DNA; COMPLEMENTARY RNA; LOCKED NUCLEIC ACID PHOSPHORAMIDITE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; DNA HYBRIDIZATION; DNA SEQUENCE; DNA SYNTHESIS; DRUG EFFECT; DRUG SCREENING; DRUG SENSITIVITY; HEAT TREATMENT; INTERMETHOD COMPARISON; MISMATCH NEGATIVITY; PROTEIN DENATURATION; STEREOSPECIFICITY;

2-AMINOPURINE; GUANINE; MAGNETIC RESONANCE SPECTROSCOPY; NUCLEIC ACID HYBRIDIZATION; OLIGONUCLEOTIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 1842666864     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.02.008     Document Type: Article

References (43)

1. Koshkin A.A., Singh S.K., Nielsen P., Rajwanshi V.K., Kumar R., Meldgaard M., Olsen C.E., Wengel J. Tetrahedron. 54:1998;3607-3630.
2. Singh S.K., Nielsen P., Koshkin A.A., Wengel J. Chem. Commun. 1998;455-456.
3. Obika S., Nanbu D., Hari Y., Andoh J.-I., Morio K.-I., Doi T., Imanishi T. Tetrahedron Lett. 39:1998;5401-5404.
4. Wengel J. LNA (Locked Nucleic Acid). Crooke S.T. Antisense Drug Technology; Principles, Strategies and Applications. 2001;339-357 Marcel Dekker, New York, Basel.
5. Cook P.D. Nucleosides Nucleotides. 18:1999;1141-1162.
6. Vorbrüggen H., Bennua B. Chem. Ber. 114:1981;1279-1286.
7. Vorbrüggen H., Höfle G. Chem. Ber. 114:1981;1256-1268.
8. Koshkin A.A., Fensholdt J., Pfundheller H.M., Lomholt C. J. Org. Chem. 66:2001;8504-8512.
9. Parel S.P., Leumann C.J. Helv. Chim. Acta. 83:2000;2514-2526.
10. Geen G.R., Kincey P.M., Spoors P.G. Tetrahedron Lett. 42:2001;1781-1784.
11. Robins M.J., Zou R., Guo Z., Wnuk S.F. J. Org. Chem. 61:1996;9207-9212.
12. Jenny T.F., Schneider K.C., Benner S.A. Nucleosides Nucleotides. 11:1992;1257-1261.
13. Kjellberg J., Johansson N.G. Nucleosides Nucleotides. 8:1989;225-256.
14. Geen G.R., Grinter T.J., Kincey P.M., Jarvest R.L. Tetrahedron. 46:1990;6903-6914.
15. Cooperwood J.S., Boyd V., Gumina G., Chu C.K. Nucleosides Nucleotides Nucleic Acids. 19:2000;219-236.
16. Lakshman M.K., Hilmer J.H., Martin J.Q., Keeler J.C., Dinh Y.Q.V., Ngassa F.N., Russon L.M. J. Am. Chem. Soc. 123:2001;7779-7787.
17. Vince R., Brownell J., Beers S.A. Nucleosides Nucleotides. 14:1995;39-44.
18. Zagórowska I., Adamiak R.W. Biochimie. 78:1996;123-130.
19. Jankowski A.J., Wise D.S., Townsend L.B. Nucleosides Nucleotides. 8:1989;339-348.
20. Brand B., Reese C.B., Song Q., Visintin C. Tetrahedron. 55:1999;5239-5252.
21. Trivedi B.K. Nucleosides Nucleotides. 7:1988;393-402.
22. Konkel M.J., Vince R. Nucleosides Nucleotides. 14:1995;2061-2077.
23. Chen X., Kern E.R., Drach J.C., Gullen E., Cheng Y.-C., Zemlicka J. J. Med. Chem. 46:2003;1531-1537.
24. Luyten I., Herdewijn P. Eur. J. Med. Chem. 33:1998;515-576.
25. Brown B., Hegedus L.S. J. Org. Chem. 65:2000;1865-1872.
26. Rhee H., Yoon D., Jung M.E. Nucleosides Nucleotides Nucleic Acids. 19:2000;619-628.
27. Reitz A.B., Rebarchak M.C. Nucleosides Nucleotides. 11:1992;1121.
28. Ashwell M., Bleasdale C., Golding B.T., O'Neill I.K. J. Chem. Soc., Chem. Commun. 1990;955-956.
29. Matteson D.S., Man H.-W., Ho O.C. J. Am. Chem. Soc. 118:1996;4560-4566.
30. Kjellberg J., Johansson N.G. Tetrahedron. 42:1986;6541-6544.
31. Chenon M.-T., Pugmire R.J., Grant D.M., Panzica R.P., Townsend L.B. J. Am. Chem. Soc. 97:1975;4627-4636.
32. Bailey S., Harnden M.R. Nucleosides Nucleotides. 6:1987;555-574.
33. Gryaznov S., Schultz R.G. Tetrahedron Lett. 35:1994;2489-2492.
34. Cano A., Goodman M.F., Eritja R. Nucleosides Nucleotides. 13:1994;501-509.
35. Cheong C., Tinoco I., Chollet A. Nucleic Acids Res. 16:1988;5115-5122.
36. Gaffney B.L., Marky L.A., Jones R.A. Tetrahedron. 40:1984;3-13.
37. Boudou V., Kerremans L., Bouvere B.D., Lescrinier E., Schepers G., Busson R., Aerschot A.V., Herdewijn P. Nucleic Acids Res. 27:1999;1450-1456.
38. Matray T., Gamsey S., Pongracz K., Gryaznov S. Nucleosides Nucleotides Nucleic Acids. 19:2000;1553-1567.
39. Wu X., Delgado G., Krisnamurthy R., Eschenmoser A. Org. Lett. 4:2002;1283-1286.
40. Petersen M., Bondensgaard K., Wengel J., Jacobsen J.P. J. Am. Chem. Soc. 124:2002;5974-5982.
41. Nielsen K.E., Petersen M., Håkansson A.E., Wengel J., Jacobsen J.P. Chem. Eur. J. 8:2002;3001-3009.
42. Woo J., Meyer R.B., Gamper H.B. Nucleic Acids Res. 24:1996;2470-2475.
43. Pedersen D.S., Rosenbohm C. Synthesis. 2001;2431-2434.