Asymmetric autocatalysis initiated by achiral nucleic acid base adenine: Implications on the origin of homochirality of biomolecules

Chemical Communications

Volumn 48, Issue 85, 2012, Pages 10538-10540

  Mineki, Hiroko ^a   Hanasaki, Taichi ^a   Matsumoto, Arimasa ^a   Kawasaki, Tsuneomi ^a   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; ADENINIUM DINITRATE; ALKANOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CRYSTAL; SPECTROSCOPY;

EID: 84867314741     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc34928k     Document Type: Article

References (61)

1. M. Bolli, R. Micura, A. Eschenmoser, Chem. Biol, 1997, 4, 309
2. Organometallic Chirality, ed. G. Pályi, C. Zucchi and L. Caglioti, Accad. Nazl. Sci. Lett. Arti, Modena, 2008
3. The Origin of Chirality in the Molecules of Life, ed. A. Guijarro and M. Yus, The Royal Society of Chemistry, Cambridge, 2009
4. R. Breslow, M. S. Levine, Proc. Natl. Acad. Sci. U. S. A, 2006, 103, 12979
5. J. R. Cronin, S. Pizzarello, Science, 1997, 275, 951
6. D. K. Kondepudi, R. Kaufman, N. Singh, Science, 1990, 250, 975
7. J. M. Ribó, J. Crusats, F. Sagues, J. Claret, R. Rubires, Science, 2001, 292, 2063
8. Y. Inoue, Chem. Rev, 1992, 92, 741
9. B. L. Feringa, R. A. Van Delden, Angew. Chem, Int. Ed, 1999, 38, 3419
10. H. B. Kagan, A. Moradpour, J. F. Nicoud, G. Balavoine, G. Tsoucaris, J. Am. Chem. Soc, 1971, 93, 2353
11. T. Kawasaki, M. Sato, S. Ishiguro, T. Saito, Y. Morishita, I. Sato, H. Nishino, Y. Inoue, K. Soai, J. Am. Chem. Soc, 2005, 127, 3274
12. I. Weissbuch, M. Lahav, Chem. Rev, 2011, 111, 3236
13. B. Kahr, R. W. Gurney, Chem. Rev, 2001, 101, 893
14. M. Sakamoto, Chem.–Eur. J, 1997, 3, 684
15. T. Matsuura, H. Koshima, J. Photochem. Photobiol, C, 2005, 6, 7
16. K. Soai, S. Osanai, K. Kadowaki, S. Yonekubo, T. Shibata, I. Sato, J. Am. Chem. Soc, 1999, 121, 11235
17. K. Mislow, Collect. Czech. Chem. Commun, 2003, 68, 849
18. K. Soai, I. Sato, T. Shibata, S. Komiya, M. Hayashi, Y. Matsueda, H. Imamura, T. Hayase, H. Morioka, H. Tabira, J. Yamamoto, Y. Kowata, Tetrahedron: Asymmetry, 2003, 14, 185
19. K. Suzuki, K. Hatase, D. Nishiyama, T. Kawasaki, K. Soai, J. Syst. Chem, 2010, 1, 5
20. D. A. Singleton, L. K. Vo, Org. Lett, 2003, 5, 4337
21. C. Girard, H. B. Kagan, Angew. Chem, Int. Ed, 1998, 37, 2923
22. M. M. Green, J.-W. Park, T. Sato, A. Teramoto, S. Lifson, R. L. B. Selinger, J. V. Selinger, Angew. Chem, Int. Ed, 1999, 38, 3139
23. C. Viedma, Phys. Rev. Lett, 2005, 94, 65504
24. T. Katagiri, C. Yoda, K. Furuhashi, K. Ueki, T. Kubota, Chem. Lett, 1996, 115
25. V. A. Soloshonok, H. Ueki, M. Yasumoto, S. Mekala, J. S. Hirschi, D. A. Singleton, J. Am. Chem. Soc, 2007, 129, 12112
26. Y. Hayashi, M. Matsuzawa, J. Yamaguchi, S. Yonehara, Y. Matsumoto, M. Shoji, D. Hashizume, H. Koshino, Angew. Chem, Int. Ed, 2006, 45, 4593
27. W. L. Noorduin, A. A. C. Bode, M. V. D. Meijden, H. Meekes, A. F. V. W. Etteger, J. P. V. Enckevort, P. C. M. Christiannen, B. Kaptein, R. M. Kellogg, T. Rasing, E. Vlieg, Nat. Chem, 2009, 1, 729
28. M. Klussmann, H. Iwamura, S. P. Mathew, D. H. Wells Jr, U. Pandya, A. Armstrong, D. G. Blackmond, Nature, 2006, 441, 621
29. S. B. Tsogoeva, S.-W. Wei, M. Freund, M. Mauksch, Angew. Chem, Int. Ed, 2009, 48, 590
30. F. C. Frank, Biochim. Biophys. Acta, 1953, 11, 459
31. K. Soai, T. Shibata, H. Morioka, K. Choji, Nature, 1995, 378, 767
32. T. Kawasaki, K. Soai, Bull. Chem. Soc. Jpn, 2011, 84, 879
33. T. Kawasaki, K. Soai, J. Fluorine Chem, 2010, 131, 525
34. K. Soai, T. Kawasak and T. Shibata, in Catalytic Asymmetric Synthesis, Third Edition, ed. I. Ojima, John Wiley & Sons Inc, Hoboken, New Jersey, 2010, ch. 12, pp. 891–930
35. K. Soai, T. Kawasaki, Top. Curr. Chem, 2008, 284, 1
36. K. Soai, T. Shibata, I. Sato, Acc. Chem. Res, 2000, 33, 382
37. T. Kawasaki, K. Soai, Isr. J. Chem, 2012, 52, 582
38. C. Bolm, F. Bienewald, A. Seger, Angew. Chem, Int. Ed, 1996, 35, 1657
39. D. G. Blackmond, Proc. Natl. Acad. Sci. U. S. A, 2004, 101, 5732
40. L. Caglioti, G. Palyi, Chim. Oggi, 2008, 26, 41
41. G. Lente, Symmetry, 2010, 2, 767
42. T. Gehring, M. Busch, M. Schlageter, D. Weingand, Chirality, 2010, 22, E173
43. I. Sato, D. Omiya, H. Igarashi, K. Kato, Y. Ogi, K. Tsukiyama, K. Soai, Tetrahedron: Asymmetry, 2003, 14, 975
44. D. G. Blackmond, C. R. McMillan, S. Ramdeehul, A. Schorm, J. M. Brown, J. Am. Chem. Soc, 2001, 123, 10103
45. I. D. Gridnev, J. M. Serafimov, J. M. Brown, Angew. Chem, Int. Ed, 2004, 43, 4884
46. L. Schiaffino, G. Ercolani, Angew. Chem, Int. Ed, 2008, 47, 6832
47. M. Quaranta, T. Gehring, B. Odell, J. M. Brown, D. G. Blackmond, J. Am. Chem. Soc, 2010, 132, 15104
48. G. Ercolani, L. Schiaffino, J. Org. Chem, 2011, 76, 2619
49. D. Lavabre, J.-C. Micheau, J. R. Isias and T. Buhse, in Amplification of Chirality, ed. K. Soai, Springer, Heidelberg, 2008, p. 67–96
50. I. D. Gridnev, A. K. Vorobiev, J. A. Raskatov, in The Soai Reaction and Related Topic, ed. G. Palyi, C. Zucchi, L. Caglioti, ch. 4, Accad. Nazl. Sci. Lett. Arti, Modena, 2012, pp. 79–122
51. J.-K. Micheau, C. Coudret and T. Buhse, in The Soai Reaction and Related Topic, ed. G. Palyi, C. Zucchi and L. Caglioti, ch. 7, Accad. Nazl. Sci. Lett. Arti, Modena, 2012, pp. 169–196
52. I. Sato, H. Urabe, S. Ishiguro, T. Shibata, K. Soai, Angew. Chem, Int. Ed, 2003, 41, 1614
53. T. Kawasaki, Y. Hakoda, H. Mineki, K. Suzuki, K. Soai, J. Am. Chem. Soc, 2010, 132, 2874
54. T. Kawasaki, K. Suzuki, Y. Hakoda, K. Soai, Angew. Chem, Int. Ed, 2008, 47, 496
55. J. Oro, Biochem. Biophys. Res. Commun, 1960, 2, 407
56. A. W. Schwartz, H. Joosten, A. B. Voet, BioSystems, 1982, 15, 191
57. G. L. Hardgrove Jr, J. R. Einstein, B. E. Hingerty, C. H. Wei, Acta Crystallogr, Sect. C, 1983, 39, 88
58. J. M. McBride, R. L. Carter, Angew. Chem, Int. Ed. Engl, 1991, 30, 293
59. C. Viedma, J. Cryst. Growth, 2004, 261, 118
60. A. Frontera, P. Gamez, M. Mascal, T. J. Mooibroek, J. Reedijk, Angew. Chem, Int. Ed, 2011, 50, 9564
61. D. J. Carter, A. L. Rohl, A. Shtukenberg, S. Bian, C. Hu, L. Baylon, B. Kahr, H. Mineki, K. Abe, T. Kawasaki, K. Soai, Cryst. Growth Des, 2012, 12, 2138