Pyrazolo[3,4-d]pyrimidine nucleic acids: Adjustment of dA-dT to dG-dC base pair stability

Nucleic Acids Research

Volumn 29, Issue 10, 2001, Pages 2069-2078

  Seela, Frank ^a   Becher, Georg ^a  

^a UNIVERSITY OF OSNABRÜCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; CYTOSINE; DEOXYRIBONUCLEOSIDE; DOUBLE STRANDED DNA; GUANINE; NUCLEIC ACID; NUCLEOSIDE DERIVATIVE; OLIGONUCLEOTIDE; PYRAZOLO[3,4 D]PYRIMIDINE DERIVATIVE; THYMINE;

ARTICLE; BASE MISPAIRING; BASE PAIRING; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; DNA HYBRIDIZATION; DNA MICROARRAY; DNA MODIFICATION; GENE SEQUENCE; GENETIC STABILITY; IMMOBILIZATION; PRIORITY JOURNAL;

EID: 0035873531     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/29.10.2069     Document Type: Article

References (34)

1. Gaffney, B.L. Marky, LA and Jones, R.A. (1984) The influence of the purine 2-amino group on DNA conformation and stability II. Tetrahedron, 40, 3-13.
2. Bailly, C. and Waring, M.J. (1998) The use of diaminopurine to investigate structural properties of nucleic acids and molecular recognition between ligands and DNA. Nucleic Acids Res., 26, 4309-4314.
3. Chollet, A. and Kawashima, E. (1988) DNA containing the base analogue 2-aminoadenine: preparation, use as hybridization probes and cleavage by restriction endonucleases. Nucleic Acids Res., 16, 305-317.
4. Chollet, A., Chollet-Damerius, A. and Kawashima, E.H. (1986) Synthesis of oligodeoxyribonucleotides containing the base 2-aminoadenine. Chem. Scripta, 26, 37-40.
5. Cheong, C., Tinoco, I.Jr and Chollet, A. (1988) Thermodynamic studies of base pairing involving 2,6-diaminopurine. Nucleic Acids Res., 16, 5115-5122.
6. Lamm, G.M., Blencowe, B.J., Sproat, B.S., Iribarren, A.M., Ryder, U. and Lamond, A.I. (1991) Antisense probes containing 2-aminoadenosine allow efficient depletion of U5 snRNP from HeLa splicing extracts. Nucleic Acids Res., 19, 3193-3198.
7. Hoheisel, J.D. and Lehrach, H. (1990) Quantitative measurements on the duplex stability of 2,6-diaminopurine and 5-chloro-uracil nucleotides using enzymatically synthesized oligomers. FEBS Lett., 274, 103-106.
8. Sagi, J., Szakonyi, E., Vorlícková, M. and Kypr, J. (1996) Unusual contribution of 2-aminoadenine to the thermostabilily of DNA. J. Biomol. Struct. Dyn., 13, 1035-1041.
9. Gryaznov, S. and Schultz, R.G. (1994) Stabilization of DNA:DNA and DNA:RNA duplexes by substitution of 2'-deoxyadenosine with 2'-deoxy-2-aminoadenosine. Tetrahedron Lett., 35, 2489-2492.
10. Haaima, G., Hansen, H.F., Christensen, L., Dahl, O. and Nielsen, P.E. (1997) Increased DNA binding and sequence discrimination of PNA oligomers containing 2,6-diamino-piarine. Nucleic Acids Res., 25, 4639-4643.
11. Boudou, V., Kerremans, L., De Bouvere, B., Lescrinier, E., Schepers, G., Busson, R., Van Aerschot, A. and Herdewijn, P. (1999) Base pairing of anhydrohexitol nucleosides with 2,6-diaminopurine, 5-methylcytosine and uracil as base moiety. Nucleic Acids Res., 27, 1450-1456.
12. Ramzaeva, N. and Seela, F. (1996) Duplex stability of 7-deazapurine DNA: oligonucleotides containing 7-bromo-or 7-iodo-7-deazaguanine. Helv. Chim. Acta, 79, 1549-1558.
13. Seela, F. and Zulauf, M. (1999) Synthesis of oligonucleotides containing pyrazolo[3,4-d]-pyrimidines: the influence of 7-substituted 8-aza-7-deazaadenines on the duplex structure and stability. J. Chem. Soc. Perkin Trans., 1, 479-488.
14. Seela, F. and Thomas, H. (1995) Duplex stabilization of DNA: oligonucleotides containing 7-substituted 7-deazaadenines. Helv. Chim. Acta, 78, 94-108.
15. Seela, F. and Becher, G. (1999) Oligonucleolides containing pyrazolo[3,4-d]pyrimidines: the influence of 7-substituled 8-aza-7-deaza-2'-deoxyguanosines on the duplex structure and stability. Helv. Chim. Acta, 82, 1640-1655.
16. Balow, G., Mohan, V., Lesnik, E.A., Johnston, J.F., Monia, B.P. and Acevedo, O.L. (1998) Biophysical andantisense properties of oligodeoxynucleotides containing 7-propynyl-, 7-iodo-and 7-cyano-7-deaza-2-amino-2'-deoxyadenosines. Nucleic Acids Res., 26, 3350-3357.
17. 9-(2'-deoxy-β-D-ribofuranosides): building blocks for solid-phase synthesis and incorporation into oligodeoxyribonucleotides. Helv. Chim. Acta, 74, 1790-1800.
18. 2 by two-dimensional NMR and simulated annealing. Biochemistry. 35, 14077-14089.
19. Seela, F. and Becher, G. (1998) Synthesis of 7-halogenated 8-aza-7-deaza-2'-deoxyguanosines and related pyrazolo[3,4-d]pyrimidine 2'-deoxyribonucleosides. Synthesis, 207-214.
20. Seela, F. and Driller, H. (1988) 8-Aza-7-deaza-2',3'-dideoxyguanosine: deoxygenation of its 2'-deoxy-β-D-ribofuranoside. Helv. Chim. Acta, 71, 757-761.
21. Cano, A., Goodman, M.F. and Eritja, R. (1994) Synthesis of oligodeoxyribonucleotides containing 2,6-diaminopurine. Nucl. Nucl., 13, 501-509.
22. McBride, L.J., Kierzek, R., Beaucage, S.L. and Caruthers, M.H. (1986) Amidine protecting groups for oligonucleotide synthesis. J. Am. Chem. Soc., 108, 2040-2048.
23. Oertel, F., Winter, H., Kazimierczuk, Z., Vilpo, J.A., Richter, P. and Seela, F. (1992) Synthesis and properties of methylthiopyrazolo[3,4-d|pyrimidine 2'-deoxy-β-D-ribonucleosides. Liebigs Ann. Chem., 1165-1170.
24. van Wijk, J. and Altona, C. (1993) PSEUROT 6.2 - A Program for the Conformational Analysis of the Five-membered Rings. University of Leiden, Leiden, The Netherlands.
25. Seela, F., Becher, G., Rosemeyer, H., Reuter, H., Kastner, G. and Mikhailopulo, I.A. (1999) The high-anti conformation of 7-halogenated 8-aza-7-deaza-2'-deoxyguanosines: a study of the influence of modified bases on the sugar structure of nucleosides. Helv. Chim. Acta, 82, 105-124.
26. Rosemeyer, H. and Seela, F. (1997) Stereoelectronic effects of modified purine bases on the sugar conformation of nucleosides: pyrrolo[2,3-d]pyrimidines. J. Chem. Soc., Perkin Trans., 2, 2341-2345.
27. Sproat, B.S., Iribarren, A.M., Garcia, R.G. and Beijer, B. (1991) New synthetic routes to synthons suitable for 2'-O-allyloligoribonucleotide assembly. Nucleic Acids Res., 19, 733-738.
28. Luyten, I., Van Aerschot, A., Rozenski, J., Busson, R. and Herdewijn, P. (1997) Protection of 2,6-diaminopurine 2'-deoxyriboside. Nucl. Nucl., 16, 1649-1652.
29. Ti, G.S., Gaffney, B.L. and Jones, R.A. (1982) Transient protection: efficient one-flask syntheses of protected deoxynucleosides. J. Am. Chem. Soc., 104, 1316-1319.
30. Sinha, N.D., Biernat, J., McManus, J. and Köster, H. (1984) Polymer support oligonucleotide synthesis XVIII: use of β-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product. Nucleic Acids Res., 12, 4539-4557.
31. Seela, F., Wei, C., Melenewski, A., He, Y., Kroschel, R. and Feiling, E. P(1999) Parallel-stranded DNA formed by new base pairs related to the isoguanine-cytosine or isocytosine-guanine motifs. Nucl. Nucl., 18, 1543-1548.
32. Vastmans, K., Pochet, S., Peys, A., Kerremans, L., Van Aerschot, A., Hendrix, C., Marlière, P. and Herdewijn, P. (2000) Enzymatic incorporation in DNA of sugar-modified nucleotides. Biochemistry, 39, 12757-12765.
33. Christensen, N.K., Petersen, M., Nielsen, P., Jacobsen, J.P., Olsen, C.E. and Wengel, J. (1998) A novel class of oligonucleotide analogues containing 2'-O,3'-C-linked [3.2.0]bicycloarabinonucleoside monomers synthesis, thermal affinity studies, and molecular modeling. J. Am. Chem. Soc., 120, 5458-5463.
34. Kimos, M.D., Khudyakov, I.Y., Alexandrushkina, N.I. and Vanyushin, B.F. (1977) 2-Aminoadenine is an adenine substituting for a base in S-2L cyanophage DNA. Nature, 270, 369-370.