The role of intramolecular hydrogen bonding on nucleobase acidification following metal coordination: Possible implications of an "indirect" role of metals in acid-base catalysis of nucleic acids

Journal of Biological Inorganic Chemistry

Volumn 10, Issue 7, 2005, Pages 800-812

  Roitzsch, Michael ^a   Añorbe, Marta Garijo ^a   Miguel, Pablo J Sanz ^a   Müller, Barbara ^a   Lippert, Bernhard ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Acid base catalysis; Intramolecular hydrogen bonding; Nucleobase; pK a shifts; Platinum

Indexed keywords

1 METHYLCYTOSINE; 1,9 DIMETHYLADENINE; ADENINE DERIVATIVE; CYTOSINE DERIVATIVE; METAL COMPLEX; NUCLEIC ACID BASE; PLATINUM COMPLEX; UNCLASSIFIED DRUG;

ACID BASE BALANCE; ARTICLE; CATALYSIS; COMPLEX FORMATION; HYDROGEN BOND; PH; PKA; PRIORITY JOURNAL;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYTOSINE; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; METALS; MODELS, MOLECULAR; NUCLEIC ACIDS; NUCLEOTIDES;

EID: 27744585288     PISSN: 09498257     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00775-005-0030-4     Document Type: Article

References (56)

1. Westhof E (1999) Science 286:61-62
2. Fedor MJ (2002) Curr Opin Struct Biol 12:289-295
3. Pyle AM (2002) J Biol Inorg Chem 7:679-690
4. Cate JH, Hanna RL, Doudna JA (1997) Nature Struct Biol 4:553-558
5. Legault P, Pardi A (1997) J Am Chem Soc 119:6621-6628
6. Perrotta AT, Shih Ih, Been MD (1999) Sciene 286:123-126
7. Muth GW, Ortoleva-Donnelly L, Strobel SA (2000) Science 289:947-950
8. Oyelere AK, Kardon JR, Strobel SA (2002) Biochemistry 41:3667-3675
9. Bevilacqua PC (2003) Biochemistry 42:2259-2265
10. Das SR, Piccirilli JA (2005) Nature Chem Biol 1:45-52
11. Sigel H (1968) Eur J Biochem 3:530-537
12. Sigel H (1969) Angew Chem 81:161-171
13. Kastner ME, Coffey KE, Clarke MJ, Edmonds SE, Eriks K (1981) J Am Chem Soc 103:5749-5752
14. Clarke MJ, Taube H (1974) J Am Chem Soc 96:5413-5419
15. Chu GYH, Mansy S, Duncan RE, Tobias RS (1978) J Am Chem Soc 100:593-606
16. Sigel H, Lippert B (1998) Pure & Appl Chem 70:845-854
17. Song B, Zhao J, Griesser R, Meiser C, Sigel H, Lippert B (1999) Chem Eur J 5:2374-2387
18. Griesser R, Kampf G, Kapinos LE, Komeda S, Lippert B, Reedijk J, Sigel H (2003) Inorg Chem 42:32-41
19. Lippert B, Schöllhorn H, Thewalt U (1992) Inorg Chim Acta 198-200:723-732
20. Lüth MS, Willermann M, Lippert B (2001) Chem Commun: 2058-2059
21. Garijo Añorbe M, Lüth MS, Roitzsch M, Morell Cerdà M, Lax P, Kampf G, Sigel H, Lippert B (2004) Chem Eur J 10:1046-1057
22. Roitzsch M, Lippert B (2004) J Am Chem Soc 126:2421-2424
23. Urry DW, Peng SQ, Parker TM, Gowda DC, Harris RD (1993) Angew Chem Int Ed Engl 32:1440-1442
24. Bevilacqua PC, Brown TS, Nakano S-i, Yajima R (2004) Biopolymers 73:90-109
25. Itaya T, Tanaka F, Fujii T (1972) Tetrahedron 28:535-547
26. Krüger G (1893) Z Physiol Chem 18:434-458
27. Kistenmacher TJ, Rossi M, Caradonna JP, Marzilli LG (1979) Adv Mol Relax Interact Processes 15:119-133
28. Kauffman GB, Cowan DO (1993) Inorg Synth 7:239-245
29. Arpalahti J, Sillanpää R, Mikola M (1994) J Chem Soc Dalton Trans:1499-1500
30. Arpalahti J, Niskanen E, Sillanpää R (1999) Chem Eur J 5:2306-2311
31. Krizanovic O, Sabat M, Beyerle-Pfnür R, Lippert B (1993) J Am Chem Soc 115:5538-5548
32. Sanz Miguel PJ (2005) PhD thesis, University of Dortmund. Full details to be reported elsewhere
33. Lippert B, Lock CJL, Speranzini RA (1981) Inorg Chem 20:808-813
34. Beyerle-Pfnür R, Brown B, Faggiani R, Lippert B, Lock CJL (1985) Inorg Chem 24:4001-4009
35. Glasoe PK, Long FA (1960) J Phys Chem 64:188-190
36. Tribolet R, Sigel H (1987) Eur J Biochem 163:353-363
37. Martin RB (1963) Science 139:1198-1203
38. Otwinowski Z, Minor W (1997) Methods Enzymol 276:307-326
39. Minor W, Cymborowski M, Otwinowski Z (2002) Acta Phys Pol A 101:513-619
40. EvalCCD, Bruker-Axs Inc., Matison, Wisconsin, USA, 2002:
41. Duisenberg AJM, Kroon-Batenburg LMJ, Schreurs AMM (2003) J Appl Cryst 36:220-229
42. SADABS: Area-detector absorption correction, Siemens Industrial Automation, Inc., Madison, Wisconsin, USA, 1996
43. Sheldrick GM, SHELXTL Plus (VMS), Siemens Analytical X-Ray Instruments, Inc.; Madison, Wisconsin, USA, 1990
44. Sheldrick GM, SHELXL-97, Programs for crystal structure refinement. Universität Göttingen, Germany, 1997
45. Stewart R, Harris MG (1977) Can J Chem 55:3807-3814
46. Sanz Miguel PJ, Lax P, Lippert B, unpublished results
47. Šponer JE, Sanz Miguel PJ, Rodriguez-Santiago L, Erxleben A, Krumm M, Sodupe M, Sponer J, Lippert B (2004) Angew Chem Int Ed 43:5396-5399
48. Klika KD, Arpalahti J (2004) Chem Commun: 666-667
49. Arpalahti J, Klika KD (1999) Eur J Inorg Chem: 1199-1201
50. Viljanen J, Klika KD, Sillanpää R, Arpalahti J (1999) Inorg Chem 38:4924-4925
51. Arpalahti J, Klika KD, Molander S (2000) Eur J Inorg Chem:1007-1013
52. Freisinger E, Schneider A, Drumm M, Hegmans A, Meier S, Lippert B (2000) J Chem Soc Dalton Trans: 2381-2387
53. Lippert B, Schöllhorn H, Thewalt U (1986) J Am Chem Soc 108:6616-6621
54. Sanz Miguel PJ, Lax P, Willermann M, Lippert B (2004) Inorg Chim Acta 357:4552-4561
55. Müller J, Glahé F, Freisinger E, Lippert B (1999) Inorg Chem 38:3160-3166
56. Frommer G, Mutikainen I, Pesch FJ, Hillgeris EC, Preut H, Lippert B (1992) Inorg Chem 31:2429-2434