Guanine-rich RNAs and DNAs that bind heme robustly catalyze oxygen transfer reactions

Journal of the American Chemical Society

Volumn 133, Issue 6, 2011, Pages 1877-1884

  Poon, Lester C H ^a   Methot, Stephen P ^a   Morabi Pazooki, William ^a   Pio, Frédéric ^a   Bennet, Andrew J ^a   Sen, Dipankar ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITE; ANTI-CANCER THERAPEUTICS; CATALYZE OXYGEN; DEOXYRIBOZYMES; G-QUADRUPLEXES; GUANINE QUADRUPLEXES; HAMMETT ANALYSIS; HIGH-RESOLUTION STRUCTURES; OXYGEN TRANSFER; RIBOZYMES; STYRENE OXIDE; THIOANISOLE; TWO-ELECTRON OXIDATION;

CATALYSIS; HYDROGEN; HYDROGEN PEROXIDE; IRON COMPOUNDS; NUCLEIC ACIDS; OXIDATION; PORPHYRINS; POSITIVE IONS; STYRENE;

OXYGEN;

ANISOLE DERIVATIVE; DEOXYRIBOZYME; DNA; DYE; FERRIC ION; GUANINE; GUANINE QUADRUPLEX; HEME; HYDROGEN PEROXIDE; INDIGO CARMINE; INDOLE; OXYGEN; OXYGEN 18; PROTEIN BCL 2; RIBOZYME; RNA; STYRENE; STYRENE OXIDE; THIOANISOLE; THIOANISOLE SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYSIS; CONTROLLED STUDY; ELECTRON; ELECTRON TRANSPORT; ENZYME ACTIVE SITE; HUMAN; ISOTOPE LABELING; KINETICS; MOLECULAR DOCKING; OXIDATION; OXYGEN TRANSPORT; PEROXIDATION; PROMOTER REGION;

ACETALDEHYDE; CATALYSIS; DNA; G-QUADRUPLEXES; HEME; HYDROGEN PEROXIDE; INDOLES; MODELS, MOLECULAR; OXYGEN; RNA; STYRENE; SULFIDES;

EID: 79951527747     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja108571a     Document Type: Article

References (60)

1. Doudna, J. A.; Cech, T. R. Nature 2002, 418, 222
2. Höbartner, C.; Silverman, S. K. Biopolymers 2007, 87, 279
3. Gilbert, W. Nature 1986, 319, 618
4. White, H. B., 3rd. J. Mol. Evol. 1976, 7, 101
5. Benner, S. A.; Ellington, A. D.; Tauer, A. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 7054
6. Eddy, S. R. Nat. Rev. Genet. 2001, 2, 919
7. Marnett, L. J.; Kennedy, T. A. In Cytochrome P450, Structure, Mechanism, and Biochemistry; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1995; pp 49 - 80.
8. Bröring, M. Organic Reactions Catalyzed by Heme Proteins. In Iron Catalysis in Organic Chemistry; Plietker, B., Ed.; Wiley-VCH Verlag GmbH Co. KGaA: Weinheim, Germany, 2008; pp 48 - 72.
9. Travascio, P.; Li, Y.; Sen, D. Chem. Biol. 1998, 5, 505
10. Li, Y.; Sen, D. Nat. Struct. Biol. 1996, 3, 743
11. Travascio, P.; Bennet, A. J.; Wang, D. Y.; Sen, D. Chem. Biol. 1999, 6, 779
12. Lipps, H. J.; Rhodes., D. Trends Cell. Biol. 2009, 19, 414
13. Kong, D. M.; Yang, W.; Wu, J.; Li, C. X.; Shen, H. X. Analyst 2010, 135, 545
14. Cheng, X.; Liu, X.; Bing, T.; Cao, Z.; Shangguan, D. Biochemistry 2009, 48, 7817
15. Kong, D. M.; Wu, J.; Ma, Y. E.; Shen, H. X. Analyst 2008, 133, 1158
16. Li, T.; Wang, E.; Dong, S. Chem. Commun. (Cambridge) 2008, 31, 3654
17. Deng, M.; Zhang, D.; Zhou, Y.; Zhou, X. J. Am. Chem. Soc. 2008, 130, 13095
18. Nakayama, S.; Sintim, H. O. J. Am. Chem. Soc. 2009, 131, 10320
19. Nakayama, S.; Sintim, H. O. Mol. Biosyst. 2010, 6, 95
20. Zhang, K.; Zhu, X.; Wang, J.; Xu, L.; Li, G. Anal. Chem. 2010, 82, 3207
21. Li, J.; Yao, J.; Zhong, W. Chem. Commun. (Cambridge) 2009, 33, 4962
22. Willner, I.; Willner, B.; Katz, E. Bioelectrochemistry 2007, 70, 2
23. Weizmann, Y.; Cheglakov, Z.; Willner, I. J. Am. Chem. Soc. 2008, 130, 17224
24. Pelossof, G.; Tel-Vered, R.; Elbaz, J.; Willner, I. Anal. Chem. 2010, 82, 4396
25. Thirstrup, D.; Baird, G. S. Anal. Chem. 2010, 82, 2498
26. Doerge, D. R. Arch. Biochem. Biophys. 1986, 244, 678
27. Fruetel, J. A.; Chang, Y. T.; Collins, J.; Loew, G.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1994, 116, 11643
28. Adam, W.; Mock-Knoblauch, C.; Saha-Möller, C. R. J. Org. Chem. 1999, 64, 4834
29. Savenkova, M. I.; Newmyer, S. L.; Ortiz de Montellano, P. R. J. Biol. Chem. 1996, 271, 24598
30. Ozaki, S.; Yang, H.-J.; Matsui, T.; Goto, Y.; Watanabe, Y. Tetrahedron: Asymmetry 1999, 10, 183
31. Tuynman, A.; Vink, M. K. S.; Dekker, H. L.; Schoemaker, H. E.; Wever, R. Eur. J. Biochem. 1998, 258, 906
32. Tuynman, A.; Schoemaker, H. E.; Wever, R. Monatsh. Chem. 2000, 131, 687
33. Harris, R. Z.; Newmyer, S. L.; Ortiz de Montellano, P. R. J. Biol. Chem. 1993, 268, 1637
34. Doerge, D. R.; Cooray, N. M.; Brewster, M. E. Biochemistry 1991, 30, 8960
35. van Rantwijk, F.; Sheldon, R. A. Curr. Opin. Biotechnol. 2000, 11, 554
36. Rojas, A. M.; Gonzalez, P. A.; Antipov, E.; Klibanov, A. M. Biotechnol. Lett. 2007, 29, 227
37. Isaacs, N. Physical Organic Chemistry; Prentice Hall: Upper Saddle River, NJ, 1996; p 152.
38. Kobayashi, S.; Nakano, M.; Kimura, T.; Schaap, A. P. Biochemistry 1987, 26, 5019
39. Corbett, M. D.; Chipko, B. R. Biochem. J. 1979, 183, 269
40. Gillam, E. M.; Notley, L. M.; Cai, H.; De Voss, J. J.; Guengerich, F. P. Biochemistry 2000, 39, 13817
41. Tuynman, A.; Spelberg, J. L.; Kooter, I. M.; Schoemaker, H. E.; Wever, R. J. Biol. Chem. 2000, 275, 3025
42. Ozaki, S.-i.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1995, 117, 7056
43. Miller, V. P.; DePillis, Ferrer, J. C.; Mauk, A. G.; Ortiz de Montellano, P. R. J. Biol. Chem. 1992, 267, 8936
44. Yi, X.; Mroczko, M.; Manoj, K. M.; Wang, X.; Hager, L. P. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12412
45. Ortiz de Montellano, P. R.; Choe, Y. S.; DePillis, G.; Catalano, C. E. J. Biol. Chem. 1987, 262, 11641
46. Ortiz de Montellano, P. R.; Grab, L. A. Biochemistry 1987, 26, 5310
47. Ator, M. A.; Ortiz de Montellano, P. R. J. Biol. Chem. 1987, 262, 1542
48. Travascio, P.; Witting, P. K.; Mauk, A. G.; Sen, D. J. Am. Chem. Soc. 2001, 123, 1337
49. Phan, A. T.; Kuryavyi, V.; Gaw, H. Y.; Patel, D. J. Nat. Chem. Biol. 2005, 1, 167
50. Dai, J.; Chen, D.; Jones, R. A.; Hurley, L. H.; Yang, D. Nucleic Acids Res. 2006, 34, 5133
51. Hersleth, H.-P.; Ryde, U.; Rydberg, P.; Görbitz, C. H.; Andersson, K. K. J. Inorg. Biochem. 2006, 100, 460
52. Gallivan, J. P.; Dougherty, D. A. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 9459
53. Yarus, M. Annu. Rev. Genet. 2002, 36, 125
54. Neidle, S.; Read, M. A. Biopolymers 2000-2001, 56, 195
55. Tucker, B. J.; Breaker, R. R. Curr. Opin. Struct. Biol. 2005, 15, 342
56. Paeschke, K.; Juranek, S.; Simonsson, T.; Hempel, A.; Rhodes, D.; Lipps, H. J. Nat. Struct. Mol. Biol. 2008, 15, 598
57. Cahoon, L. A.; Seifert, H. S. Science 2009, 325, 764
58. Atamna, H.; Boyle, K. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 3381
59. Wardman, P. Curr. Pharm. Des. 2002, 8, 1363
60. Elbaz, J.; Shlyahovsky, B.; Willner, I. A. Chem. Commun. 2008, 13, 1569