Syntheses and base-pairing properties of locked nucleic acid nucleotides containing hypoxanthine, 2,6-diaminopurine, and 2-aminopurine nucleobases

Journal of Organic Chemistry

Volumn 69, Issue 11, 2004, Pages 3711-3718

  Koshkin, Alexei A ^a  

^a Exiqon AS   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; ISOMERS; MOLECULAR STRUCTURE; MONOMERS; STEREOCHEMISTRY;

NUCLEOTIDES;

DNA;

2 AMINOPURINE; 2,6 DIAMINOPURINE; 6 CHLORO 2 AMINOPURINE; 9 (2 O ACETYL 3 O BENZYL 4 C METHANESULFONOXYMETHYL 5 O METHANESULFONYL BETA DEXTRO ERYTHRO PENTAFURANOSYL)HYPOXANTHINE; 9 (2 O ACETYL 3 O BENZYL 4 C METHANESULFONOXYMETHYL 5 O METHANESULFONYL BETA DEXTRO ERYTHRO PENTOFURANOSYL) 2 AMINO 6 CHLOROPURINE; DNA; HYPOXANTHINE DERIVATIVE; NUCLEIC ACID; NUCLEIC ACID BASE; NUCLEOTIDE; OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BASE MISPAIRING; BASE PAIRING; BINDING AFFINITY; DNA STRUCTURE; HYBRIDIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 2442676544     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0303923     Document Type: Article

References (58)

1. (a) Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, 455.
2. (b) Koshkin, A. A.; Singh, S. K.; Nielsen, P.; Rajwanshi, V. K.; Kumar, R.; Meldgaard, M.; Olsen, C. E.; Wengel, J. Tetrahedron 1998, 54, 3607.
3. (c) Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Morio, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401.
4. (d) Koshkin, A. A.; Rajwanshi, V. K.; Wengel, J. Tetrahedron Lett. 1998, 39, 4381.
5. (e) Koshkin, A. A.; Nielsen, P.; Meldgaard, M.; Rajwanshi, V. K.; Singh, S. K.; Wengel, J. J. Am. Chem. Soc. 1998, 120, 13252.
6. (f) Wengel, J. Acc. Chem. Res. 1999, 32, 301.
7. (g) Petersen, M.; Wengel, J. Trends Biotechnol. 2003, 21, 74-81.
8. (a) Nielsen, C. B.; Singh, S. K.; Wengel, J.; Jacobsen, J. P. J. Biomol. Struct. Dyn. 1999, 17, 175.
9. (b) Nielsen, K. E.; Singh, S. K.; Wengel, J.; Jacobsen, J. P. Bioconj. Chem. 2000, 11, 228.
10. (c) Petersen, M.; Nielsen, C. B.; Nielsen, K. E.; Jensen, G. A.; Bondensgaard, K.; Singh, S. K.; Rajwanshi, V. K.; Koshkin, A. A.; Dahl, B. M.; Wengel, J.; Jacobsen, J. P. J. Mol. Recognit. 2000, 13, 44.
11. (d) Bondensgaard, K.; Petersen, M.; Singh, S. K.; Rajwanshi, V. K.; Kumar, R.; Wengel, J.; Jacobsen, J. P. Chem. Eur. J. 2000, 6, 2687.
12. (e) Egli, M.; Minasov, G.; Teplova, M.; Kumar, R.; Wengel, J. Chem. Commun. 2001, 651.
13. (a) Obika, S.; Uneda, T.; Sugimoto, T.; Nanbu, D.; Minami, T.; Doi, T.; Imanishi, T. Bioorg. Med. Chem. 2001, 9, 1001.
14. (b) Imanishi, T.; Obika, S. Chem. Commun. 2002, 1653.
15. (a) Wahlestedt, C.; Salmi, P.; Good, L.; Kela, J.; Johnsson, T.; Hökfelt, T.; Broberger, C.; Porreca, F.; Lai, J.; Ren, K.; Ossipov, M.; Koshkin, A.; Jakobsen, N.; Skouv, J.; Ørum, H.; Jacobsen, M. H.; Wengel, J. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 5633.
16. (b) Chernolovskaya, E. L.; Koshkin, A. A.; Vlassov, V. V. Nucleosides Nucleotides Nucleic Acids 2001, 20, 847.
17. (c) Kurreck, J.; Wyszko, E.; Gillen, C.; Erdmann, V. A. Nucleic Acids Res. 2002, 9, 1911.
18. (d) Crinelli, R.; Bianchi, M.; Gentilini, L.; Magnani, M. Nucleic Acids Res. 2002, 11, 2435.
19. (e) Elayadi, A. N.; Braasch, D. A.; Corey, D. R. Biochemistry 2002, 41, 9973.
20. (a) Ørum, H.; Jakobsen, M. H.; Koch, T.; Vuust, J.; Borre, M. B. Clin. Chem. 1999, 45, 1898.
21. (b) Jacobsen, N.; Fenger, M.; Bentzen, J.; Rasmussen, S. L.; Jakobsen, M. H.; Fenstholt, J.; Skov, J. Clin. Chem. 2002, 48, 657.
22. Koshkin, A. A.; Fensholdt, J.; Pfundheller, H. M.; Lomholt, C. J. Org. Chem. 2001, 66, 8504.
23. Liu, H.; Nicols, R. Biotechniques 1994, 16, 24-26.
24. (a) Martin, F. H.; Castro, M. M.; Aboul-ela, F.; Tinoco, I. Nucleic Acids Res. 1985, 13, 8927-8938.
25. (b) Van Aerschot, A.; Peeters, B.; van Derhaeghe, H. Nucleotides Nucleosides 1987, 6, 437-439.
26. (c) Seela, F.; Chen, Y. Nucleic Acids Res. 1995, 23, 2499-2505.
27. (a) Chollet, A.; Kawashima, E. Nucleic Acids Res. 1988, 16, 305-317.
28. (b) Chazin, W. J.; Rance, H.; Chollet, A.; Leupin, W. Nucleic Acids Res. 1991, 19, 5507-5513.
29. (c) Hoheisel, J. D.; Lehrah, H. FEBS Lett. 1990, 27, 103-106.
30. Cheong, C.; Tinoco, I.; Chollet, A. Nucleic Acids Res. 1988, 16, 5115.
31. Howard, F. B.; Miles, H. T. Biopolymers 1983, 22, 6131.
32. Boudou, V.; Kerremans, L.; De Bouvere, B.; Lescrinier, E.; Schepers, G.; Busson, R.; Van Aerschot, A.; Herdewijn, P. Nucleic Acids Res. 1999, 27, 1450.
33. Timofeev, E.; Mirzabekov, A. Nucleic Acids Res. 2001, 29, 2626-2634.
34. Kutyavin, I. V.; Rhinehart, R. L.; Lukhtanov, E. A.; Gorn, V. V.; Meyer, R. B.; Gamper, H. B. Biochemistry 1996, 35, 11170.
35. (a) O'Neill, M. A.; Barton, J. K. J. Am. Chem. Soc. 2002, 124, 13053.
36. (b) Holz, B.; Klimasauskas, S.; Serva, S.; Weinhold, E. Nucleic Acids Res. 1998, 26, 1076.
37. (c) Diekmann, S.; von Kitzing, E.; McLaughlin, L.; Ott, J.; Eckstein, F. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8257.
38. (d) Seela, F.; Becher, G. Helv. Chim. Acta 2000, 83, 928.
39. (e) Jean, J. M.; Hall, K. B. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 37.
40. (a) Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
41. (b) Vorbrüggen, H.; Höfie, G. Chem. Ber. 1981, 114, 1256.
42. (c) Vorbrügen, H. Acta Biochim. Pol. 1996, 43, 25.
43. (a) McBride, L. J.; Caruthers, M. H. Tetrahedron Lett. 1983, 24, 245.
44. (b) Nielsen, J.; Taagaard, M.; Marugg, J.; van Boom, J. H.; Dahl, O. Nucleic Acids Res. 1986, 14, 7391.
45. (c) Sinha, N. D.; McManus, J.; Köster, H. Nucleic Acids Res. 1984, 12, 4539.
46. Martin, P. Helv. Chim. Acta 1995, 78, 486.
47. See for example: (a) Fathi, R.; Goswami, B.; Kung, P.-P.; Gaffney, B. L. ; Jones, R. A. Tetrahedron Lett. 1990, 31, 319.
48. (b) Gryaznov, S.; Schultz, R. G. Tetrahedron Lett. 1994, 35, 2489.
49. (c) Lakshman, M. K.; Ngassa, F. N.; Keeler, J. C.; Dinh, Y. Q. V.; Hilmer, J. H.; Russon, L. M. Org. Lett. 2000, 2, 927.
50. Koch, T.; Jensen, F. R. Improved synthesis of purine locked nucleic acid analogues. International Patent WO 02/28875 A2, April 11, 2002.
51. Frieden, M.; Avino, A.; Eritja, R. Nucleosides Nucleotides Nucleic Acids 2003, 22, 193.
52. McBride, L. J.; Kierzek, R.; Beaucage, S. L.; Caruthers, M. H. J. Am. Chem. Soc. 1986, 108, 2040.
53. Pedersen, D. S.; Rosenbohm, C.; Koch, T. Synthesis 2002, 802.
54. Caruthers, M. H. Acc. Chem. Res. 1991, 24, 278.
55. Borah, B.; Cohen, J. S.; Howard, F. B.; Miles, H. T. Nucleic Acids Res. 1985, 24, 7456.
56. Rosenbohm, C.; Christensen, S. M.; Sørensen, M. D.; Pedersen, D. S.; Larsen, L.-E.; Wengel, J.; Koch, T. Org. Biomol. Chem. 2003, 1, 655.
57. (a) Håkansson, A. E.; Koshkin, A. A.; Sørensen, M. D.; Wengel, J. J. Org. Chem. 2060, 65, 5161.
58. (b) Sorensen, M. D.; Kvørnø, L.; Bryld, T.; Håkansson, A. E.; Verbeure, B.; Gaubert, G.; Herdewijn, P.; Wengel, J. J. Am. Chem. Soc. 2002, 124, 2164.