Synthesis, Stability, and Protonation Studies of a Self-Complementary Dodecamer Containing the Modified Nucleoside 2′-Deoxyzebularine

Biopolymers

Volumn 73, Issue 1, 2004, Pages 27-43

  Vives, M ^a   Eritja, R ^b   Tauler, R ^a   Marquez, V E ^c   Gargallo, R ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUT DE BIOLOGIA MOLECULAR DE BARCELONA   (Spain)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

2 deoxyzebularine; DNA sructure; Factor analysis; Multivariate Curve Resolution; Spectroscopy

Indexed keywords

ACETIC ACID; DEGRADATION; NUCLEIC ACIDS; PH EFFECTS; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL); TITRATION;

PROTONATION;

BIOPOLYMERS;

2' DEOXYZEBULARINE; ACID; AMMONIA; BASE; HYDROXYL GROUP; NUCLEOSIDE DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE; PYRIMIDINONE DERIVATIVE; TRICHLOROACETIC ACID; TRITYL DERIVATIVE; UNCLASSIFIED DRUG; ZEBULARINE;

ACID BASE BALANCE; ARTICLE; DEGRADATION; EQUILIBRIUM CONSTANT; MELTING POINT; MOLECULAR STABILITY; PH; PKA; PROTON TRANSPORT; SPECTROSCOPY; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTIDINE; DNA; HYDROGEN-ION CONCENTRATION; KINETICS; MASS SPECTROMETRY; MODELS, THEORETICAL; NUCLEIC ACID CONFORMATION; OLIGODEOXYRIBONUCLEOTIDES; PROTONS; PYRIMIDINE NUCLEOSIDES; SPECTROMETRY, FLUORESCENCE; TEMPERATURE; TIME FACTORS;

EID: 0347763714     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/bip.10515     Document Type: Article

References (30)

1. Barchi, J. J.; Haces, A.; Marquez, V. E.; McCormack, J. J. Nucleosides Nucleotides 1992, 11, 1781-1793.
2. Barchi, J. J.; Musser, S.; Marquez, V. E. J Org Chem 1992, 57, 536-541.
3. Driscoll, J. S.; Marquez, V. E.; Plowman, J.; Liu, P. S.; Kelley, J. A.; Barchi, J. J. J Med Chem 1991, 34, 3280-3284.
4. Adams, C. J.; Murray, J. B.; Arnold, J. R. P.; Stockley, P. G. Tetrahedron Lett 1994, 35, 1597-1600.
5. Iocono, J. A.; Gildea, G.; McLaughlin, L. W. Tetrahedron Lett 1990, 31, 145-178.
6. Berthet, N.; Constant, J. F.; Demeunynck M.; Michon, P.; Lhomme, J. J Med Chem 1997, 40, 3346-3352.
7. Baik, M. H.; Friesner, R. A.; Lippard, S. J Am Chem Soc 2002, 124, 4495-4503.
8. Basu, A. K.; O'Hara, S. M.; Valladier, P.; Stone, K.; Mols, O.; Marnett, L. J. Chem Res Toxicol 1988, 1, 53-59.
9. Nair, V.; Turner, G. A.; Offerman, R. J. J Am Chem Soc 1984, 106, 3370-3371.
10. Brown, T.; Brown, D. J. S. In Oligonucleotides and analogues, a practical approach; Eckstein, F., Ed.; IRL Press: Oxford, 1991, pp. 1-25.
11. Gildea, B.; McLaughlin, L. W. Nucleic Acids Res 1989, 17, 2261-2281.
12. Zhou, Y.; Ts'o, P. O. Nucleic Acids Res 1996, 24, 2652-2659.
13. Gargallo, R.; Tauler, R.; Izquierdo-Ridorsa, A. Biopolymers 1997, 42, 271-283.
14. Vives, M.; Gargallo, R.; Tauler, R. Biopolymers 2001, 59, 477-488.
15. Dyson, R.; Kaderli, S.; Lawrence, G. A.; Maeder, M.; Zuberbühler, A. D. Anal Chim Acta 1997, 353, 381-393.
16. Tauler, R.; Smilde, A.; Kowalski, B. R. J Chemom 1995, 9, 31-58.
17. Jaumot, J.; Escaja, N.; Gargallo, R.; González, C.; Pedroso, E.; Tauler, R. Nucleic Acids Res 2002, 30:e92.
18. Gargallo, R.; Vives, M.; Tauler, R.; Eritja, R. Biophys J 2001, 81, 2886-2896.
19. Vives, M.; Gargallo, R.; Tauler, R. Anal Chem 1999, 71, 4328-4337.
20. Maeder, M.; Zilian, A. Chemom Intel Lab Syst 1988, 3, 205-213.
21. Windig, W.; Stephenson, D. A. Anal Chem 1992, 64, 2735-2742.
22. Golub, G. H.; Van Loan, C. F. Matrix Computations, Johns Hopkins University Press: Baltimore, 1989.
23. Izquierdo-Ridorsa, A.; Saurina, J.; Hemández-Cassou, S.; Tauler, R. Chemom Intell Lab Syst 1997, 38, 183-196.
24. Saurina, J.; Hernández-Casou, S.; Tauler, R.; Izquierdo-Ridorsa, A. J Chemom 1998, 12, 183-203.
25. Amhrein, M.; Sirnivaman, B.; Bonvin, D.; Schumacher, M. Chemom Intell Lab Syst 1996, 33, 17-33.
26. Matlab® routines available at http://www.ub.es/gesq/mcr/mcr.htm
27. Fox, J. J.; Van Praag, D.; Wempen, I.; Doerr, I. L.; Cheong, L.; Knoll, J. E.; Eidinoff, M. L.; Bendich, A. B.; George, B. J Am Chem Soc 1959, 81, 178-187.
28. Izatt, R. M.; Christensend, J. J.; Rytting, J. H. Chem Rev 1971, 71, 439-480.
29. Gargallo, R.; Tauler, R.; Izquierdo-Ridorsa, A. Anal Chim Acta 1996, 331, 195-205.
30. Davis, T. M.; McFail-Isom, L.; Keane, E.; Williams, L. D. Biochem 1998, 37, 6795-6798.