Synthesis and triple helix-forming ability of oligonucleotides with N,N- dimethylaminoethyl phosphoramidate linkages

Tetrahedron Letters

Volumn 40, Issue 39, 1999, Pages 7131-7134

  Robles, Jordi ^a   Ibáñez, Víctor ^a   Grandas, Anna ^a   Pedroso, Enrique ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE;

ARTICLE; SYNTHESIS; THERMOSTABILITY; TRIPLE HELIX;

EID: 0033600703     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01478-1     Document Type: Article

References (20)

1. 1. Soyfer, V. N.; Potaman, V. N. Triple Helical Nucleic Acids; Springer Verlag, New York, 1996.
2. 2. Ref. 1, Chapter 4, pp. 151-193.
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4. 4. a) Letsinger, R. L.; Singman, C. N.; Histand, G.; Salunkhe, M. J. Am. Chem. Soc. 1988, 110, 4470-4471;
5. b) Bailey, C. D.; Dagle, J. M.; Weeks, D. L. Nucleic Acids Res. 1998, 26, 4860-4867.
6. 5. a) Jung, P. M.; Histand, G.; Letsinger, R. L. Nucleosides Nucleotides 1994, 13, 1597-1605;
7. b) Horn, T.; Chatuverdi, S.; Balasubramanian, T. N.; Letsinger, R. L. Tetrahedron Lett. 1996, 37, 743-746;
8. c) Chatuverdi, S.; Horn, T.; Letsinger, R. L. Nucleic Acids Res. 1996, 24, 2318-2323.
9. 6. Froehler, B. C. Tetrahedron Lett. 1986, 27, 5575-5578.
10. 7. Matteucci, M.; Lin, K.-Y.; Butcher, S.; Moulds, C. J. Am. Chem. Soc. 1991, 113, 7767-7768.
11. 8. In modified strands, "+" is used to indicate cationic phosphoramidate internucleoside linkages and "-" anionic phosphate diesters.
12. 9. Jäger, A.; Levy, M. J.; Hecht, S. M. Biochemistry 1988, 27, 7237-7246.
13. 10. Polushin, N. N.; Morocho, A. M.; Chen, B.-C.; Cohen, J. S. Nucleic Acids Res. 1994, 22, 639-645.
14. 2O + N-methylimidazole in lutidine/THF, 2 min.
15. 12. 1 and 2 were obtained in 3 % and 8 % synthesis and purification yield, respectively, and characterized by MALDI-TOF mass spectrometry (negative mode): 1 (m/z): 2379.4, 4739.9; 2 (m/z): 2362.4, 4742.0. Theoretical average mass for 1 and 2 (neutral form): 4736.4 Da.
16. 2. 1 μg of snake venom phosphodiesterase (E.C. 3.1.3.1, Boehringer Mannheim) was added to 250 μL of the buffer solution, and the reaction mixture was incubated at 37 °C. At regular intervals, aliquots were removed, frozen and lyophilized. These aliquots were subsequently analyzed by reversed phase HPLC to determine the ratio of undegraded oligonucleotide.
17. 6 linker was introduced as the corresponding phosphoramidite derivative, which was prepared as described in Rumney, S.; Kool, E. T. J. Am. Chem. Soc., 1995, 117, 5635-5646.
18. 111 (melting temperature) refers to the midpoint of the region of maximun slope for each transition in the the plot of absorbance versus temperature.
19. 2, and oligonucleotides were present at approximately 1 μM concentration.
20. 17. Plum, G. E.; Breslauer, K. J. J. Mol. Biol. 1995, 248, 678-695.