Isoguanine and 5-Methyl-Isocytosine Bases, In Vitro and In Vivo

Chemistry - A European Journal

Volumn 21, Issue 13, 2015, Pages 5009-5022

  Bande, Omprakash ^a   Abu El Asrar, Rania ^a   Braddick, Darren ^b   Dumbre, Shrinivas ^a   Pezo, Valérie ^b,c   Schepers, Guy ^a   Pinheiro, Vitor B ^d   Lescrinier, Eveline ^a   Holliger, Philipp ^e   Marlière, Philippe ^b   Herdewijn, Piet ^a,b  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b Institute of Systems and Synthetic Biology   (France)

^c DIF   (France)

^d UNIVERSITY COLLEGE LONDON   (United Kingdom)

^e MRC LABORATORY OF MOLECULAR BIOLOGY   (United Kingdom)

Author keywords

HNA; isoG; nucleosides; polymerase; XNA plasmid

Indexed keywords

MOBILE SECURITY; NUCLEIC ACIDS;

HNA; ISOG; NUCLEOSIDES; POLYMERASE; XNA PLASMID;

BIOMOLECULES;

5 METHYLCYTOSINE; 5-METHYL ISOCYTOSINE; GUANINE; ISOGUANINE; NUCLEOSIDE;

ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY;

5-METHYLCYTOSINE; GUANINE; MOLECULAR STRUCTURE; NUCLEOSIDES;

EID: 84924727530     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201406392     Document Type: Article

References (44)

1. P. Herdewijn, P. Marliere, Chem. Biodiversity 2009, 6, 791-808.
2. a) S. A. Benner, A. M. Sismour, Nat. Rev. Genet. 2005, 6, 533-543;
3. b) V. B. Pinheiro, P. Holliger, Curr. Opin. Chem. Biol. 2012, 16, 245-252;
4. c) J. C. Chaput, H. Yu, S. Zhang, Chem. Biol. 2012, 19, 1360-1371.
5. a) S. Pochet, P. A. Kaminski, A. Van Aerschot, P. Herdewijn, P. Marlière, C. R. Biol. 2003, 326, 1175-1184;
6. b) A. T. Krueger, L. W. Peterson, J. Chelliserry, D. J. Kleinbaum, E. T. Kool, J. Am. Chem. Soc. 2011, 133, 18447-18451;
7. c) V. Pezo, F. W. Liu, M. Abramov, M. Froeyen, P. Herdewijn, P. Marlière, Angew. Chem. Int. Ed. 2013, 52, 8139-8143;
8. Angew. Chem. 2013, 125, 8297-8301;
9. d) V. Pezo, G. Schepers, C. Lambertucci, P. Marliere, P. Herdewijn, ChemBioChem 2014, 15, 2255-2258;
10. e) 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.
11. P. Marlière, J. Patrouix, V. Döring, P. Herdewijn, S. Tricot, S. Cruveiller, M. Bouzon, R. Mutzel, Angew. Chem. Int. Ed. 2011, 50, 7109-7114;
12. Angew. Chem. 2011, 123, 7247-7252.
13. V. B. Pinheiro, A. I. Taylor, C. Cozens, M. Abramov, M. Renders, S. Zhang, J. C. Chaput, J. Wengel, S. Y. Peak-Chew, S. H. McLaughlin, P. Herdewijn, P. Holliger, Science 2012, 336, 341-344.
14. a) Z. Kazimierczuk, D. Shugar, Acta Biochim. Pol. 1973, 20, 395;
15. b) Z. Kazimierczuk, R. Mertens, W. Kawczynski, F. Seela, Helv. Chim. Acta 1991, 74, 1742-1748.
16. T. Golas, M. Fikus, Z. Kazimierczuk, D. Shugar, Eur. J. Biochem. 1976, 65, 183-192.
17. A. Rich, Horizons in Biochemistry (Eds.: M. Kasha, B. Pullman), Academic Press, New York, 1962, pp. 103-126.
18. a) Y. Tor, P. B. Dervan, J. Am. Chem. Soc. 1993, 115, 4461-4467;
19. b) T. Horn, C.-A. Chang, M. L. Collins, Tetrahedron Lett. 1995, 36, 2033-2036.
20. C. Y. Switzer, S. E. Moroney, S. A. Benner, Biochemistry 1993, 32, 10489-10496.
21. S. C. Johnson, C. B. Sherrill, D. J. Marshall, M. J. Moser, J. R. Prudent, Nucleic Acids Res. 2004, 32, 1937-1941.
22. F. Seela, C. Wei, Z. Kazimierczuk, Helv. Chim. Acta 1995, 78, 1843-1854.
23. T. A. Martinot, S. A. Benner, J. Org. Chem. 2004, 69, 3972-3975.
24. F. Seela, X. Peng, H. Li, J. Am. Chem. Soc. 2005, 127, 7739-7751.
25. D. Jiang, F. Seela, J. Am. Chem. Soc. 2010, 132, 4016-4024.
26. Z. Yang, F. Chen, J. B. Alvarado, S. A. Benner, J. Am. Chem. Soc. 2011, 133, 15105-15112.
27. a) P. Herdewijn, Chem. Biodiversity 2010, 7, 1-59;
28. b) C. Hendrix, H. Rosemeyer, B. De Bouvere, A. Van Aerschot, F. Seela, P. Herdewijn, Chem. Eur. J. 1997, 3, 1513-1520.
29. O. Bande, P. Herdewijn, Eur. J. Org. Chem. 2014, 231-236.
30. J. R. Prudent, C. B. Sherrill, WO2006127009 A1, 2010.
31. I. Verheggen, A. Van Aerschot, S. Toppet, R. Snoeck, G. Janssen, J. Balzarini, E. De Clercq, P. Herdewijn, J. Med. Chem. 1993, 36, 2033-2040.
32. V. Boudou, L. Kerremans, B. De Bouvere, E. Lescrinier, G. Schepers, R. Busson, A. Van Aerschot, P. Herdewijn, Nucleic Acids Res. 1999, 27, 1450-1456.
33. F. Seela, C. Wei, Helv. Chim. Acta 1999, 82, 726-745.
34. F. Seela, Y. He, C. Wei, Tetrahedron 1999, 55, 9481-9500.
35. E. E. Swayze, A. M. Siwkowski, B. Bhat, T. P. Prakash, C. Allerson, P. P. Seth, Isis Pharmaceuticals, Inc., US, 2010.
36. S. C. Jurczyk, J. T. Kodra, J. H. Park, S. A. Benner, T. R. Battersby, Helv. Chim. Acta 1999, 82, 1005-1015.
37. J. Ludwig, Acta Biochim. Biophys. Acad. Sci. Hung. 1981, 16, 131-133.
38. J. Ludwig, F. Eckstein, J. Org. Chem. 1989, 54, 631-635.
39. H. Kamiya, H. Kasai, J. Biol. Chem. 1995, 270, 19446-19450.
40. A. M. Sismour, S. A. Benner, Nucleic Acids Res. 2005, 33, 5640-5646.
41. H. Robinson, Y. G. Gao, C. Bauer, C. Roberts, C. Switzer, A. H. J. Wang, Biochemistry 1998, 37, 10897-10905.
42. a) S. A. Strobel, T. R. Cech, N. Usman, L. Beigelman, Biochemistry 1994, 33, 13824-13835;
43. b) S. A. Strobel, T. R. Cech, Biochemistry 1996, 35, 1201-1211.
44. A. Giraut, R. Abu El-Asrar, P. Marliere, M. Delarue, P. Herdewijn, ChemBioChem 2012, 13, 2439-2444.