Asymmetric autocatalysis induced by chiral crystals of achiral tetraphenylethylenes

Origins of Life and Evolution of Biospheres

Volumn 40, Issue 1, 2010, Pages 65-78

  Kawasaki, Tsuneomi ^a   Nakaoda, Mai ^a   Kaito, Nobuhiro ^a   Sasagawa, Taisuke ^a   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Amplification of chirality; Asymmetric autocatalysis; Hemihedral crystal; Origin of chirality; Spontaneous chiral crystallization; Tetraphenylethylenes

Indexed keywords

ALDEHYDE; ALKALI METAL; AMORPHOUS MEDIUM; CATALYST; CRYSTALLIZATION; ETHYLENE; HYDROCARBON; RADICAL; SPECTROSCOPY;

ETHYLENE; ETHYLENE DERIVATIVE;

ARTICLE; BIOGENESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CRYSTALLIZATION; STEREOISOMERISM;

BIOGENESIS; CATALYSIS; CRYSTALLIZATION; ETHYLENES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77949344389     PISSN: 01696149     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11084-009-9183-4     Document Type: Article

References (66)

1. Avalos M, Babiano R, Cintas P, Jiménez JL, Palacios JC (2000) Chiral autocatalysis: where stereochemistry meets the origin of life. Chem Commun 11: 887-892.
2. Blackmond DG (2004) Asymmetric autocatalysis and its implications for the origin of homochirality. Proc Natl Acad Sci USA 101(16): 5732-5736.
3. Blackmond DG, McMillan CR, Ramdeehul S, Schorm A, Brown JM (2001) Origins of asymmetric amplification in autocatalytic alkylzinc additions. J Am Chem Soc 123(41): 10103-10104.
4. Bolm C, Bienewald F, Seger A (1996) Asymmetric autocatalysis with amplification of chirality. Angew Chem Int Ed Engl 35(15): 1657-1659.
5. Bonner WA (1995) Chirality and life. Origins Life Evol Biosphere 25(1-3): 175-190.
6. Bonner WA, Rubenstein E (1987) Supernovae, neutron stars and biomolecular chirality. BioSystems 20(1): 99-111.
7. Buhse T (2003) A tentative kinetic model for chiral amplification in autocatalytic alkylzinc additions. Tetrahedron Asymmetr 14(8): 1055-1061.
8. Caglioti L, Zucchi C, Pályi G (2005) Single-molecule chirality. Chim Oggi 23(5): 38-39 42-43.
9. Claborn K, Isborn C, Kaminsky W, Kahr B (2008) Optical rotation of achiral compounds. Angew Chem Int Ed 47(31): 5706-5717.
10. Eschenmoser A (1999) Chemical etiology of nucleic acid structure. Science 284(5423): 2118-2124.
11. Feringa BL, van Delden RA (1999) Absolute asymmetric synthesis: the origin, control, and amplification of chirality. Angew Chem Int Ed 38(23): 3419-3438.
12. Flack HD (1983) Foundations of crystallography. Acta Cryst A39(6): 876-881.
13. Girard C, Kagan HB (1998) Nonlinear effects in asymmetric synthesis and stereoselective reactions: ten years of investigation. Angew Chem Int Ed 37(21): 2923-2959.
14. Green BS, Lahav M, Rabinovich D (1979) Asymmetric synthesis via reactions in chiral crystals. Acc Chem Res 12: 191-197.
15. Green MM, Park J-W, Sato T, Teramoto A, Lifson S, Selinger RLB, Selinger JV (1999) The macromolecular route to chiral amplification. Angew Chem Int Ed 38(21): 3139-3154.
16. Gridnev ID (2006) Chiral symmetry breaking in chiral crystallization and Soai autocatalytic reaction. Chem Lett 35(2): 148-153.
17. Gridnev ID, Serafimov JM, Brown JM (2004) Solution structure and reagent binding of the zinc alkoxide catalyst in the Soai asymmetric autocatalytic reaction. Angew Chem Int Ed 43(37): 4884-4887.
18. Hazen RM (2004) Chiral crystal faces of common rock-forming minerals. In: Palyi G, Zucchi C (eds) Progress in biological chirality. Elsevier, Oxford, pp 137-151.
19. Hazen RM, Sholl DS (2003) Chiral selection on inorganic crystalline surfaces. Nature Materials 2(6): 367-374.
20. Hoekstra A, Vos A (1975) Crystal and molecular structures of tetraphenylhydrazine and related compounds at -160°C. II. Crystal structures of tetraphenylethylene (TPE) and diphenylaminotriphenylmethane (DTM). Acta Cryst B 31(6): 716-721.
21. Inoue Y (1992) Asymmetric photochemical reactions in solution. Chem Rev 92(5): 741-770.
22. Islas JS, Lavabre D, Grevy JM, Lamoneda RH, Cabrera HR, Micheau JC, Buhse T (2005) Mirror-symmetry breaking in the Soai reaction: a kinetic understanding. Proc Natl Acad Sci USA 102(39): 13743-13748.
23. Kahr B, Gurney RW (2001) Dyeing crystals. Chem Rev 101(4): 893-951.
24. Kawasaki T, Jo K, Igarashi H, Sato I, Nagano M, Koshima H, Soai K (2005a) Asymmetric amplification using chiral cocrystals formed from achiral organic molecules by asymmetric autocatalysis. Angew Chem Int Ed 44(18): 2774-2777.
25. Kawasaki T, Sato M, Ishiguro S, Saito T, Morishita Y, Sato I, Nishino H, Inoue Y, Soai K (2005b) Enantioselective synthesis of near enantiopure compound by asymmetric autocatalysis triggered by asymmetric photolysis with circularly polarized light. J Am Chem Soc 127(10): 3274-3275.
26. Kawasaki T, Suzuki K, Hatase K, Otsuka M, Koshima H, Soai K (2006a) Enantioselective synthesis mediated by chiral crystal of achiral hippuric acid in conjunction with asymmetric autocatalysis. Chem Commun 1869-1871.
27. Kawasaki T, Tanaka H, Tsutsumi T, Kasahara T, Sato I, Soai K (2006b) Chiral discrimination of cryptochiral saturated quaternary and tertiary hydrocarbons by asymmetric autocatalysis. J Am Chem Soc 128(18): 6032-6033.
28. Kawasaki T, Hatase K, Fujii Y, Jo K, Soai K, Pizzarello S (2006c) The distribution of chiral asymmetry in meteorites: an investigation using asymmetric autocatalytic chiral sensors. Geochim Cosmochim Acta 70(21): 5395-5402.
29. Kawasaki T, Harada Y, Suzuki K, Tobita T, Florini N, Palyi G, Soai K (2008a) Enantioselective synthesis utilizing enantiomorphous organic crystal of achiral benzils as a source of chirality in asymmetric autocatalysis. Org Lett 10(18): 4085-4088.
30. Kawasaki T, Suzuki K, Hakoda Y, Soai K (2008b) Achiral nucleobase cytosine acts as an origin of homochirality of biomolecules in conjunction with asymmetric autocatalysis. Angew Chem Int Ed 47(3): 496-499.
31. 12C) chirality. Science 324(5926): 492-495.
32. Klankermayer J, Gridnev ID, Brown JM (2007) Role of the isopropyl group in asymmetric autocatalytic zinc alkylations. Chem Commun 3151-3153.
33. Kondepudi DK, Asakura K (2001) Chiral autocatalysis, spontaneous symmetry breaking, and stochastic behavior. Acc Chem Res 34(12): 946-954.
34. Kuhn W, Knopf EZ (1930) The preparation of optically active compounds by the aid of light. Physik Chem B 7: 292-310.
35. Kuroda R (2004) Circular dichroism in the solid state. Mol Supramol Photochem 11(Chiral Photochemistry): 385-413.
36. Lente GJ (2004) Homogeneous chiral autocatalysis: a simple, purely stochastic kinetic model. Phys Chem A 108(44): 9475-9478.
37. Maddox J (1998) What Remains to be discovered: mapping the secrets of the universe, the origins of life, and the future of the human race. Free, New York.
38. Maeda K, Okamoto Y, Morlender N, Haddad N, Eventova I, Biali SE, Rappoport Z (1995) Does the threshold enantiomerization route of crowded tetraarylethenes involve double bond rotation? J Am Chem Soc 117(38): 9686-9689.
39. Matsuura T, Koshima H (2005) Introduction to chiral crystallization of achiral organic compounds spontaneous generation of chirality. J Photochem Photobiol C: Photochem Rev 6(1): 7-24.
40. Micskei K, Pota G, Caglioti L, Pályi G (2006) Empirical description of chiral autocatalysis. J Phys Chem A 110(18): 5982-5984.
41. Mikami K, Yamanaka M (2003) Symmetry breaking in asymmetric catalysis: racemic catalysis to autocatalysis. Chem Rev 103(8): 3369-3400.
42. Mislow K (2003) Absolute asymmetric synthesis: a commentary. Collect Czech Chem Commun 68(5): 849-864.
43. Penzien K, Schmidt GM (1969) Reactions in chiral crystals: an absolute asymmetric synthesis. Angew Chem Int Ed Engl 8(8): 608-609.
44. Podlech J (2001) Origin of organic molecules and biomolecular homochirality. Cell Mol Life Sci 58(1): 44-60.
45. Podlech J, Gehring T (2005) New aspects of Soai's asymmetric autocatalysis. Angew Chem Int Ed 44(36): 5776-5777.
46. Saito Y, Hyuga H (2004) Complete homochirality induced by nonlinear autocatalysis and recycling. J Phys Soc Jpn 73(1): 33-35.
47. Sakamoto M (1997) Absolute asymmetric synthesis from achiral molecules in the chiral crystalline environment. Chem Eur J 3(5): 684-689.
48. Sato I, Kadowaki K, Soai K (2000) Asymmetric synthesis of an organic compound with high enantiomeric excess induced by inorganic ionic sodium chlorate. Angew Chem Int Ed 39(8): 1510-1512.
49. Sato I, Urabe H, Ishiguro S, Shibata T, Soai K (2003a) Amplification of chirality from extremely low to greater than 99. 5% ee by asymmetric autocatalysis. Angew Chem Int Ed 42(3): 315-317.
50. Sato I, Omiya D, Igarashi H, Kato K, Ogi Y, Tsukiyama K, Soai K (2003b) Relationship between the time, yield, and enantiomeric excess of asymmetric autocatalysis of chiral 2-alkynyl-5-pyrimidyl alkanol with amplification of enantiomeric excess. Tetrahedron Asymmetr 14(8): 975-979.
51. Sato I, Kadowaki K, Ohgo Y, Soai K (2004) Highly enantioselective asymmetric autocatalysis induced by chiral ionic crystals of sodium chlorate and sodium bromate. J Mol Cat A: Chemical 216(2): 209-214.
52. Schiaffino L, Ercolani G (2008) Unraveling the mechanism of the Soai asymmetric autocatalytic reaction by first-principles calculations: induction and amplification of chirality by self-assembly of hexamolecular complexes. Angew Chem Int Ed 47(36): 6832-6835.
53. Shibata T, Yamamoto J, Matsumoto N, Yonekubo S, Osanai S, Soai K (1998) Amplification of a slight enantiomeric imbalance in molecules based on asymmetric autocatalysis: the first correlation between high enantiomeric enrichment in a chiral molecule and circularly polarized light. J Am Chem Soc 120(46): 12157-12158.
54. Shibata T, Yonekubo S, Soai K (1999) Practically perfect asymmetric autocatalysis using 2-alkynyl-5-pyrimidylalkanol. Angew Chem Int Ed 38(5): 659-661.
55. Soai K, Kawasaki T (2006) Discovery of asymmetric autocatalysis with amplification of chirality and its implication in chiral homogeneity of biomolecules. Chirality 18(7): 469-478.
56. Soai K, Kawasaki T (2007) Asymmetric autocatalysis and its implications in the origin of chiral homogeneity of biomolecules. In: Christmann M, Braese S (eds) Asymmetric synthesis. Wiley-VCH, Weinheim, pp 212-216.
57. Soai K, Kawasaki T (2008) Asymmetric autocatalysis with amplification of chirality. Top Curr Chem 284: 1-33.
58. Soai K, Shibata T, Morioka H, Choji K (1995) Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule. Nature 378(6559): 767-768.
59. Soai K, Shibata T, Sato I (2000) Enantioselective automultiplication of chiral molecules by asymmetric autocatalysis. Acc Chem Res 33(6): 382-390.
60. Soai K, Sato I, Shibata T (2001) Asymmetric autocatalysis and the origin of chiral homogeneity in organic compounds. Chem Record 1(4): 321-332.
61. Soai K, Sato I, Shibata T, Komiya S, Hayashi M, Matsueda Y, Imamura H, Hayase T, Morioka H, Tabira H, Yamamoto J, Kowata Y (2003) Asymmetric synthesis of pyrimidyl alkanol without adding chiral substances by the addition of diisopropylzinc to pyrimidine-5-carbaldehyde in conjunction with asymmetric autocatalysis. Tetrahedron Asymmetr 14(2): 185-188.
62. Soai K, Shibata T, Sato I (2004) Discovery and development of asymmetric autocatalysis. Bull Chem Soc Jpn 77(6): 1063-1073.
63. Tanaka K, Toda F (2000) Solvent-free organic synthesis. Chem Rev 100(3): 1025-1074.
64. Tanaka K, Fujimoto D, Altreuther A, Oeser T, Irngartinger H, Toda F (2000) Chiral inclusion crystallization of achiral tetrakis(p-halophenyl)-ethylenes with achiral guest compounds. Perkin 2(10): 2115-2120.
65. Todd MH (2002) Asymmetric autocatalysis: product recruitment for the increase in the chiral environment (PRICE). Chem Soc Rev 31(4): 211-222.
66. Weissbuch I, Leiserowitz L, Lahav M (2005) Stochastic "Mirror symmetry breaking" via self-assembly, reactivity and amplification of chirality: Relevance to abiotic conditions. Top Curr Chem 259: 123-165.