Chemical Morphing of DNA Containing Four Noncanonical Bases

Angewandte Chemie - International Edition

Volumn 55, Issue 26, 2016, Pages 7515-7519

  Eremeeva, Elena ^a   Abramov, Michail ^a   Margamuljana, Lia ^a   Rozenski, Jef ^a   Pezo, Valerie ^b   Marlière, Philippe ^b   Herdewijn, Piet ^a,b  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b Institute of Systems and Synthetic Biology   (France)

Author keywords

chemical evolution; DNA replication; gene expression; nucleic acids; synthetic biology

Indexed keywords

DNA; ESCHERICHIA COLI; GENE ENCODING; GENE EXPRESSION; MACHINERY; NUCLEIC ACIDS; NUCLEOTIDES; SYNTHETIC BIOLOGY;

BACTERIAL REPLICATION; CHEMICAL EVOLUTION; DEOXYADENOSINE; DIHYDROFOLATE REDUCTASE; DNA POLYMERASE; DNA REPLICATIONS; MODIFIED DNA; NUCLEOTIDE TRIPHOSPHATES;

POLYMERASE CHAIN REACTION;

2'-DEOXY-7-DEAZAGUANOSINE TRIPHOSPHATE; 2'-DEOXYTUBERCIDIN; 5-CHLORO-2'-DEOXYURIDINE; 5-FLUORO-2'-DEOXYCYTIDINE; DEOXYCYTIDINE; DEOXYGUANOSINE PHOSPHATE; DEOXYURIDINE; DNA; TRIMETHOPRIM; TUBERCIDIN;

ANALOGS AND DERIVATIVES; CHEMISTRY; DRUG EFFECT; ESCHERICHIA COLI; POLYMERASE CHAIN REACTION; PROCEDURES; TRIMETHOPRIM RESISTANCE;

DEOXYCYTIDINE; DEOXYGUANINE NUCLEOTIDES; DEOXYURIDINE; DNA; ESCHERICHIA COLI; POLYMERASE CHAIN REACTION; TRIMETHOPRIM; TRIMETHOPRIM RESISTANCE; TUBERCIDIN;

EID: 84966670161     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201601529     Document Type: Article

References (49)

1. J. D. Watson, F. H. C. Crick, Nature 1953, 171, 964–967.
2. J. B. Opalinska, A. M. Gewirtz, Nat. Rev. Drug Discovery 2002, 1, 503–514;
3. L. P. Jordheim, D. Durantel, F. Zoulim, C. Dumontet, Nat. Rev. Drug Discovery 2013, 12, 447–464.
4. L. E. Orgel, The Origins of Life: Molecules and Natural Selection, Wiley, New York, NY, 1973;
5. M. W. Powner, B. Gerland, J. D. Sutherland, Nature 2009, 459, 239–242.
6. V. Pezo, F. W. Liu, M. Abramov, M. Froeyen, P. Herdewijn, P. Marlière, Angew. Chem. Int. Ed. 2013, 52, 8139–8143;
7. Angew. Chem. 2013, 125, 8297–8301;
8. V. Pezo, G. Schepers, C. Lambertucci, P. Marlière, P. Herdewijn, ChemBioChem 2014, 15, 2255–2258.
9. T. W. Kim, J. C. Delaney, J. M. Essigmann, E. T. Kool, Proc. Natl. Acad. Sci. USA 2005, 102, 15803–15808;
10. J. C. Delaney, J. Gao, H. Liu, N. Shrivastav, J. M. Essigmann, E. T. Kool, Angew. Chem. Int. Ed. 2009, 48, 4524–4527;
11. Angew. Chem. 2009, 121, 4594–4597;
12. J. Chelliserrykattil, H. Lu, A. H. F. Lee, E. T. Kool, ChemBioChem 2008, 9, 2976–2980;
13. A. T. Krueger, L. W. Peterson, J. Chelliserry, D. J. Kleinbaum, E. T. Kool, J. Am. Chem. Soc. 2011, 133, 18447–18451.
14. H. Maruyama, K. Furukawa, H. Kamiya, N. Minakawa, A. Matsuda, Chem. Commun. 2015, 51, 7887–7890.
15. A. H. El-Sagheer, A. P. Sanzone, R. Gao, A. Tavassoli, T. Brown, Proc. Natl. Acad. Sci. USA 2011, 108, 11338–11343;
16. A. P. Sanzone, A. H. El-Sagheer, T. Brown, A. Tavassoli, Nucleic Acids Res. 2012, 40, 10567–10575;
17. C. N. Birts, A. P. Sanzone, A. H. El-Sagheer, J. P. Blaydes, T. Brown, A. Tavassoli, Angew. Chem. Int. Ed. 2014, 53, 2362–2365;
18. Angew. Chem. 2014, 126, 2394–2397.
19. D. A. Malyshev, K. Dhami, T. Lavergne, T. Chen, N. Dai, J. M. Foster, I. R. Corrêa, F. E. Romesberg, Nature 2014, 509, 385–388.
20. T. Kojima, K. Furukawa, H. Maruyama, N. Inoue, N. Tarashima, A. Matsuda, N. Minakawa, ACS Synth. Biol. 2013, 2, 529–536.
21. M. Andreola, C. Calmels, J. Michel, J.-J. Toulmé, S. Litvak, Eur. J. Biochem. 2000, 267, 5032–5040;
22. F. J. Ghadessy, N. Ramsay, F. Boudsocq, D. Loakes, A. Brown, S. Iwai, A. Vaisman, R. Woodgate, P. Holliger, Nat. Biotechnol. 2004, 22, 755–759.
23. S. Jäger, G. Rasched, H. Kornreich-Leshem, M. Engeser, O. Thum, M. Famulok, J. Am. Chem. Soc. 2005, 127, 15071–15082;
24. S. Jäger, M. Famulok, Angew. Chem. Int. Ed. 2004, 43, 3337–3340;
25. Angew. Chem. 2004, 116, 3399–3403.
26. M. Kimoto, R. Yamashige, K. Matsunaga, S. Yokoyama, I. Hirao, Nat. Biotechnol. 2013, 31, 453–457;
27. J. D. Vaught, C. Bock, J. Carter, T. Fitzwater, M. Otis, D. Schneider, J. Rolando, S. Waugh, S. K. Wilcox, B. E. Eaton, J. Am. Chem. Soc. 2010, 132, 4141–4151;
28. L. Gold, D. Ayers, J. Bertino, C. Bock, A. Bock, E. N. Brody, J. Carter, A. B. Dalby, B. E. Eaton, T. Fitzwater, et al., PLoS One 2010, 5, e15004;
29. L. Zhang, Z. Yang, K. Sefah, K. M. Bradley, S. Hoshika, M.-J. Kim, H.-J. Kim, G. Zhu, E. Jimenez, S. Cansiz, et al., J. Am. Chem. Soc. 2015, 137, 6734–6737;
30. M. Hollenstein, C. J. Hipolito, C. H. Lam, D. M. Perrin, ChemBioChem 2009, 10, 1988–1992.
31. H. Macíčková-Cahovthoma, M. Hocek, Nucleic Acids Res. 2009, 37, 7612–7622;
32. H. Macíčková-Cahová, R. Pohl, M. Hocek, ChemBioChem 2011, 12, 431–438;
33. P. Kielkowski, N. L. Brock, J. S. Dickschat, M. Hocek, ChemBioChem 2013, 14, 801–804;
34. M. Mačková, S. Boháčová, P. Perlíková, L. Poštová Slavětínská, M. Hocek, ChemBioChem 2015, 16, 2225–2236;
35. F. Seela, A. Röling, Nucleic Acids Res. 1992, 20, 55–61.
36. P. Marlière, J. Patrouix, V. Döring, P. Herdewijn, S. Tricot, S. Cruveiller, M. Bouzon, R. Mutzel, Angew. Chem. Int. Ed. 2011, 50, 7109–7114;
37. Angew. Chem. 2011, 123, 7247–7252.
38. H. Cahová, R. Pohl, L. Bednárová, K. Nováková, J. Cvacka, M. Hocek, Org. Biomol. Chem. 2008, 6, 3657–3660.
39. J. A. Law, S. E. Jacobsen, Nat. Rev. Genet. 2010, 11, 204–220.
40. V. Valinluck, W. Wu, P. Liu, J. W. Neidigh, L. C. Sowers, Chem. Res. Toxicol. 2006, 19, 556–562;
41. W. H. Ang, S. J. Lippard, Chem. Commun. 2009, 5820–5822;
42. S. K. Grime, R. L. Martin, B. L. Holaway, Nucleic Acids Res. 1991, 19, 2791;
43. T. Gourlain, A. Sidorov, N. Mignet, S. J. Thorpe, S. E. Lee, J. A. Grasby, D. M. Williams, Nucleic Acids Res. 2001, 29, 1898–1905.
44. E. E. Howell, ChemBioChem 2005, 6, 590–600.
45. N. Brisson, T. Hohn, Gene 1984, 28, 271–275.
46. A. E. Koch, J. J. Burchall, Appl. Microbiol. 1971, 22, 812–817.
47. S. Kruspe, U. Hahn, Angew. Chem. Int. Ed. 2014, 53, 10541–10544;
48. Angew. Chem. 2014, 126, 10711–10715;
49. M. E. Drew, J. C. Morris, Z. Wang, L. Wells, M. Sanchez, S. M. Landfear, P. T. Englund, J. Biol. Chem. 2003, 278, 46596–46600.