Homochirality and chemical evolution: New vistas and reflections on recent models

Tetrahedron Asymmetry

Volumn 21, Issue 9-10, 2010, Pages 1030-1040

  Ávalos, Martín ^a   Babiano, Reyes ^a   Cintas, Pedro ^a   Jiménez, José L ^a   Palacios, Juan C ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PREBIOTIC AGENT;

CHIRALITY; CRYSTALLIZATION; DEFENSE MECHANISM; EVAPORATION; HYPOTHESIS; PRIORITY JOURNAL; REVIEW; SOLID;

EID: 77956688552     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.03.049     Document Type: Review

References (165)

1. G.H. Wagnire On Chirality and the Universal Asymmetry. Reflections on Image and Mirror Image 2007 Verlag Helvetica Chimica Acta and Wiley-VCH Zürich and Weinheim
2. U. Meierhenrich Amino Acids and the Asymmetry of Life 2008 Springer Berlin
3. A. Guijarro, and M. Yus The Origin of Chirality in the Molecules of Life 2009 The Royal Society of Chemistry Cambridge
4. O.B. Ramsay Stereochemistry 1981 Heyden London
5. F.C. Frank Biochem. Biophys. Acta 11 1953 459 463
6. F.C. Frank Discuss. Faraday Soc. 25 1958 19 28
7. M. De Min, G. Levy, and J.C. Micheau J. Chim. Phys. 85 1988 603 619 and references cited therein
8. M. Avalos, R. Babiano, P. Cintas, J.L. Jiménez, and J.C. Palacios Tetrahedron: Asymmetry 11 2000 2845 2874
9. G. Nicolis, and I. Prigogine Proc. Natl. Acad. Sci. U.S.A. 78 1981 659 663
10. D.K. Kondepudi, R.J. Kaufman, and N. Singh Science 250 1990 975 976
11. E. Havinga Biochim. Biophys. Acta 13 1954 171 174
12. R.E. Pincock, R.R. Perkins, A.S. Ma, and K.R. Wilson Science 174 1971 1018 1020
13. The mechanism operating on crystal surfaces may be complex. In a related system undergoing symmetry breaking under stirring or melting (1,1′-binaphthyl) the role of inhomogeneities has been assessed as they can cause significant variations in ees: R. Plasson, D.K. Kondepudi, and K. Asakura J. Phys. Chem. B 110 2006 8481 8487
14. K. Iwamoto Phys. Chem. Chem. Phys. 5 2003 3616 3621
15. Y. Saito, and H. Hyuga J. Phys. Soc. Jpn. 73 2004 33 35
16. Y. Saito, and H. Hyuga J. Phys. Soc. Jpn. 74 2005 1629 1635
17. R. Plasson, H. Bersini, and A. Commeyras Proc. Natl. Acad. Sci. U.S.A. 101 2004 16733 16738
18. R. Plasson, D.K. Kondepudi, H. Bersini, A. Commeyras, and K. Asakura Chirality 19 2007 589 600
19. J.R. Islas, D. Lavabre, J.M. Grevy, R.H. Lamoneda, H.R. Cabrera, J.C. Micheau, and T. Buhse Proc. Natl. Acad. Sci. U.S.A. 102 2005 13743 13748
20. D.G. Blackmond Tetrahedron: Asymmetry 17 2006 584 589
21. M. Mauksch, S.B. Tsogoeva, S. Wei, and I.M. Martynova Chirality 19 2007 816 825
22. D.G. Blackmond, and O.K. Matar J. Phys. Chem. B 112 2008 5098 5104
23. R. Plasson J. Phys. Chem. B 112 2008 9550 9552
24. D.G. Blackmond J. Phys. Chem. B 112 2008 9553 9555
25. M. Mauksch, and S.B. Tsogoeva ChemPhysChem 9 2008 2359 2371
26. D.G. Blackmond Angew. Chem., Int. Ed. 48 2009 386 390
27. R. Plasson, and H. Bersini J. Phys. Chem. B 113 2009 3477 3490
28. M. Eigen Naturwiss 58 1971 465 523
29. T. Gánti BioSystems 7 1975 15 21
30. K. Soai, S. Niwa, and H. Hori J. Chem. Soc., Chem. Commun. 1990 982 983
31. K. Soai, T. Shibata, H. Morioka, and K. Choji Nature 378 1995 767 768
32. D.A. Singleton, and L.K. Vo J. Am. Chem. Soc. 124 2002 10010 10011
33. D.A. Singleton, and L.K. Vo Org. Lett. 5 2003 4337 4339
34. T. Kawasaki, Y. Matsumura, T. Tsutsumi, K. Suzuki, M. Ito, and K. Soai Science 324 2009 492 495
35. F.B. Panosyan, and J. Chin Org. Lett. 5 2003 3947 3949
36. C. Viedma Phys. Rev. Lett. 94 2005 065504(1) 065504(4)
37. C. Viedma Astrobiology 7 2007 312 319
38. W.A. Bonner Top. Stereochem. 18 1988 1 96 and references therein
39. For recent analyses and calculations: A.J. MacDermott, T. Fu, G.O. Hyde, R. Nakatsuka, and A.P. Coleman Origins Life Evol. Biosphere 39 2009 407 437
40. A.J. MacDermott, G.O. Hyde, and A.J. Cohen Origins Life Evol. Biosphere 39 2009 439 457
41. A.J. MacDermott, T. Fu, R. Nakatsuka, A.P. Coleman, and G.O. Hyde Origins Life Evol. Biosphere 39 2009 459 478
42. With larger PVEDs, some amplification mechanisms could still be reliable within a geological (or cosmological) time scale; for well-known hypotheses: D.K. Kondepudi BioSystems 20 1987 75 83
43. D.K. Kondepudi, and G.W. Nelson Nature 314 1985 438 441
44. G. Lente J. Phys. Chem. A 110 2006 12711 12713
45. F. Faglioni, A. Passalacqua, and P. Lazzeretti Origins Life Evol. Biosphere 35 2005 461 475
46. G. Lente J. Phys. Chem. A 109 2005 11058 11063
47. G. Lente, and T. Ditrói J. Phys. Chem. A 113 2009 7237 7242
48. Selective symmetry breaking by cryptochiral impurities of environmental origin has also been suggested: C. Viedma Cryst. Growth Des. 7 2007 553 556
49. Y. Nagata, T. Fujiwara, K. Kawaguchi-Nagata, Y. Fukumori, and T. Yamanaka Biochim. Biophys. Acta 1379 1998 76 82
50. H. Lam, D.-C. Oh, F. Cava, C.N. Takacs, J. Clardy, M.A. De Pedro, and M.K. Waldor Science 325 2009 1552 1555
51. J.S. Siegel Chirality 10 1998 24 27
52. For a general overview on the origin of life: Hazen, R. M. Genesis: The Scientific Quest for Lifes Origins, Joseph Henry Press: Washington, DC, 2005; for a discussion of the main theories, see Part II (pp 83-93) and Part IV (pp 205-213).
53. S.L. Miller Science 117 1953 528
54. A.P. Johnson, H.J. Cleaves, J.P. Dworkin, D.P. Glavin, A. Lazcano, and J.L. Bada Science 322 2008 404
55. Ref. 2, pp 125-127.
56. Nevertheless, it has been argued that hydrothermal vents all have both high-and low-temperature sites within short distances, and turbulence will facilitate mixing of such environments leading to moderate temperatures; for a correspondence on this and related issues: Science 2002, 298, 747-749.
57. For an excellent and comprehensive treatment of such processes, see Ref. 2, Chapter 6.2, pp 107-124; see also Chapter 7.3, pp 127-143, and references therein.
58. S. Pizzarello, Y. Huang, and M.R. Alexandre Proc. Natl. Acad. Sci. U.S.A. 105 2008 3700 3704
59. Experiments point to stereospecific syntheses of sugar precursors by amino acids and peptides: S. Pizzarello, and A.L. Weber Science 303 2004 1151
60. A.L. Weber, and S. Pizzarello Proc. Natl. Acad. Sci. U.S.A. 103 2006 12713 12717
61. S. Pizzarello, and A.L. Weber Origins Life Evol. Biosphere 40 2010 3 10
62. Z.P. Zagorski Origins Life Evol. Biosphere 37 2007 351 355
63. Z.P. Zagorski Rad. Phys. Chem. 66 2003 329 334
64. C. Huber, and G. Wächtershäuser Science 314 2006 630 632
65. C. Huber, W. Eisenreich, and G. Wächtershäuser Tetrahedron Lett. 51 2010 1069 1071
66. C. Huber, W. Eisenreich, S. Hecht, and G. Wächtershäuser Science 301 2003 938 940
67. G.D. Cody, N.Z. Boctor, T.R. Filley, R.M. Hazen, J.H. Scott, A. Sharma, and H.S. Yoder Jr. Science 289 2000 1337 1340
68. For a comprehensive treatment of the chemo-autotrophic theory: G. Wächtershäuser Prog. Biophys. Mol. Biol. 58 1992 85 201
69. For shorter perspectives: G. Wächtershäuser Microbiol. Rev. 52 1988 452 484
70. G. Wächtershäuser Proc. Natl. Acad. Sci. U.S.A. 87 1990 200 204
71. For further correspondence between both groups: Science 2007, 315, 937-939.
72. G. Wächtershäuser Med. Hypotheses 36 1991 307 311
73. See Ref. 3, Chapter 8, pp 125-132, and references therein.
74. L.E. Orgel PloS Biol. 6 2008 e18 (pp 0005-0013)
75. See: G. Zubay, and T. Mui Origins Life Evol. Biosphere 31 2001 87 102
76. A. Ricardo, M.A. Carrigan, A.N. Olcott, and S.A. Benner Science 303 2004 196
77. In a recent release, it has been shown that silicate ions, which are present at relatively high concentrations in Earths surface waters, catalyze the formation of four-and six-carbon sugars via the formose reaction. Silicate selects for sugars with a given configuration and prevents them from rapid decomposition: J.L. Lambert, S.A. Gurusamy-Thangavelu, and K. Ma Science 327 2010 984 986
78. D.G. Blackmond Angew. Chem., Int. Ed. 48 2009 2648 2654
79. See for instance: R. Wallace, and R.G. Wallace Origins Life Evol. Biosphere 38 2008 419 455
80. Despite being rather paradoxical, the so-called Red Queen argument has often been invoked in evolutionary theory and could be extended to prebiotic systems. In short, the RQ hypothesis (named after the Red Queen in Lewis Carrolls Through the Looking-Glass and What Alice Found There) holds that stochastic changes follow a constantly changing environment: L. VanAlen Evol. Theor. 1 1973 1 30
81. For recent developments in evolution: C. Venditti, A. Meade, and M. Pagel Nature 463 2010 349 352
82. For an excellent treatment: E.L. Eliel, and S.H. Wilen Stereochemistry of Organic Compounds 1994 Wiley New York pp 153-295
83. L. Zhang, A. Peritz, and E. Meggers J. Am. Chem. Soc. 124 2005 4174 4175
84. R. Stern, and M.J. Jedrzejas Chem. Rev. 108 2008 5061 5085
85. K. Ikehara Chem. Rec. 5 2005 107 118
86. M.P. Powner, B. Gerland, and J.D. Sutherland Nature 459 2009 239 242
87. Urquhart, J. Chem. World 2009 (May 13): see the link at http://www.rsc.org/chemistryworld/News/2009/May/13050902.asp (accessed May 2009).
88. It remains unsolved how purine ribonucleotides might have formed. For a commentary: J.W. Szostak Nature 459 2009 171 172
89. M. Avalos, R. Babiano, P. Cintas, J.L. Jiménez, and J.C. Palacios Origins Life Evol. Biosphere 34 2004 391 405
90. D.G. Blackmond, and M. Klussmann Chem. Commun. 2007 3990 3996
91. P. Cintas Angew. Chem., Int. Ed. 47 2008 2918 2920
92. C.J. Welch Chirality 13 2001 425 427
93. I. Ostromisslensky Ber. 41 1908 3035 3046
94. S. Kojo, and K. Tanaka Chem. Commun. 2001 1980 1981
95. S. Kojo, H. Uchino, M. Yoshimura, and K. Tanaka Chem. Commun. 2004 2146 2147
96. T. Munegumi, A. Shimoyama, and K. Harada Chem. Lett. 1997 393 394
97. Z. Takats, S.C. Nanita, and R.G. Cooks Angew. Chem., Int. Ed. 42 2003 3521 3523
98. S.C. Nanita, and R.G. Cooks Angew. Chem., Int. Ed. 45 2006 554 569
99. R. Breslow, and M.S. Levine Proc. Natl. Acad. Sci. U.S.A. 103 2006 12979 12980
100. R. Breslow, and Z.-L. Cheng Proc. Natl. Acad. Sci. U.S.A. 106 2009 9144 9146
101. M. Klussmann, H. Iwamura, S.P. Mathew, D.H. Wells Jr., U. Pandya, A. Armstrong, and D.G. Blackmond Nature 441 2006 621 623
102. For a clear-cut and recommendable treatment of racemic and enantioenriched mixtures, see Ref. 3, Sect. 5.6, pp 91-96, and references therein.
103. B.M. Rode Peptides 20 1999 773 786
104. K. Plankensteiner, H. Reiner, and B.M. Rode Chem. Biodiv. 1 2004 1308 1315
105. H. Reiner, K. Plankensteiner, D. Fitz, and B.M. Rode Chem. Biodiv. 3 2006 611 621
106. For an excellent survey of syntheses of peptides from activated amino acids, linked to prebiotic conditions: R. Pascal, L. Boiteau, and A. Commeyras P. Walde, Prebiotic Chemistry, Topics in Current Chemistry Vol. 259 2005 Springer Berlin 69 122
107. M. Levine, C. Kenesky, D. Mazori, and R. Breslow Org. Lett. 10 2008 2433 2436
108. For a longer discussion: R. Breslow, M. Levine, and Z.-L. Cheng Origins Life Evol. Biosphere 40 2010 11 26
109. S. Vandenbussche, G. Vandenbussche, J. Reisse, and K. Bartik Eur. J. Org. Chem. 2006 3069 3073
110. A. Bellec, and J.-C. Guillemin Chem. Commun. 46 2010 1482 1484
111. A. Bellec, and J.-C. Guillemin J. Fluorine Chem. 131 2010 545 548
112. M. Albrecht, V.A. Soloshonok, L. Schrader, M. Yasumoto, and M.A. Suhm J. Fluorine Chem. 131 2010 495 504
113. For a review on chirality recognition in the gas phase: A. Zehnacker, and M.A. Suhm Angew. Chem., Int. Ed. 47 2008 6970 6992
114. F.S. Kipping, and W.J. Pope J. Chem. Soc., Trans. 73 1898 606 617
115. C. Viedma J. Cryst. Growth 261 2004 118 121
116. J.H.E. Cartwright, J.M. Garcia-Ruiz, O. Piro, C.I. Sainz-Diaz, and I. Tuval Phys. Rev. Lett. 93 2004 035502(1) 035502(4)
117. W.L. Noorduin, T. Izumi, A. Millemaggi, M. Leeman, H. Meekes, W.J.P. Van Enckevort, R.M. Kellogg, B. Kaptein, E. Vlieg, and D.G. Blackmond J. Am. Chem. Soc. 130 2008 1158 1159
118. B. Kaptein, W.L. Noorduin, H. Meekes, W.J.P. Van Enckevort, R.M. Kellogg, and E. Vlieg Angew. Chem., Int. Ed. 47 2008 7226 7229
119. C. Viedma, J.E. Ortiz, T. De Torres, T. Izumi, and D.G. Blackmond J. Am. Chem. Soc. 130 2008 15274 15275
120. P.S.M. Cheung, J. Gagnon, J. Surprenant, Y. Tao, H. Xu, and L.A. Cuccia Chem. Commun. 2008 987 989
121. P.S.M. Cheung, and L.A. Cuccia Chem. Commun. 2009 1337 1338
122. For a recent and concise revision: W.L. Noorduin, E. Vlieg, R.M. Kellogg, and B. Kaptein Angew. Chem., Int. Ed. 48 2009 9600 9606 and references therein
123. W.L. Noorduin, P. Van der Asdonk, H. Meekes, W.J.P. Van Enckevort, B. Kaptein, M. Leeman, R.M. Kellogg, and E. Vlieg Angew. Chem., Int. Ed. 48 2009 3278 3280
124. W.L. Noorduin, A.A.C. Bode, M. Van der Meijden, H. Meekes, A.F. Van Etteger, W.J.P. Van Enckevort, P.C.M. Christianen, B. Kaptein, R.M. Kellogg, T. Rasing, and E. Vlieg Nat. Chem. 1 2009 729 732
125. J.H.E. Cartwright, O. Piro, and I. Tuval Phys. Rev. Lett. 98 2007 165501(1) 165501(4)
126. W.L. Noorduin, H. Meekes, A.A.C. Bode, W.J.P. Van Enckevort, B. Kaptein, R.M. Kellogg, and E. Vlieg Cryst. Growth Des. 8 2008 1675 1681
127. R. Plasson, and A. Brandenburg Origins Life Evol. Biosphere 40 2010 93 110
128. The interview, conducted by E. Punset, appeared in a Spanish TV program, REDES (interview #111), devoted to scientific divulgation (not yet available on the Internet).
129. For some highly-cited papers addressing this concern: H. Kuhn, and J. Waser Angew. Chem., Int. Ed. Engl. 20 1981 500 520
130. V.A. Avetisov, S.A. Anikin, V.I. Goldanskii, and V.V. Kuzmin Dokl. Akad. Nauk SSSR-Biophys. 282 1985 115 117
131. V.I. Goldanskii, and V.V.Z. Kuzmin Phys. Chem. 269 1988 216 274
132. G.F. Joyce, G.M. Visser, C.A.A. Van Boeckel, J.H. Van Boom, L.E. Orgel, and J. Van Westrenen Nature 310 1984 602 604
133. A.A. Beaudry, and G.F. Joyce Science 257 1992 635 641
134. D.P. Bartel, and J.W. Szostak Science 261 1993 1411 1418
135. V. Avetisov, and V. Goldanskii Proc. Natl. Acad. Sci. U.S.A. 93 1996 11435 11442
136. M. Bolli, R. Micura, and A. Eschenmoser Chem. Biol. 4 1997 309 320
137. For a succinct revision of these arguments against biotic theories, see Ref. 2, Sect. 3.4.3., pp 56-59.
138. Other models, however, based on the bifurcation theory suggest that long homochiral polymers are possible in the presence of substantial enantiomeric cross-inhibition; see: Sandars, P. G. H. Origins Life Evol. Biosphere. 2003, 33, 575-587.
139. Siegel correctly points out (Ref. 29) that the problem it is not the origin of chirality, but rather how to break the inexorable racemic state.
140. M.M. Green, and B.A. Garetz Tetrahedron Lett. 25 1984 2831 2834
141. For a good discussion on this point, see Ref. 3, Sect. 2.2.2., pp 10-17.
142. For a revision of dynamic supramolecular chirality: A.R.A. Palmans, and E.W. Meijer Angew. Chem., Int. Ed. 46 2007 8948 8968
143. For a revision of hydrodynamic forces involved in asymmetric selection: J. Crusats, Z. El-Hachemi, and J.M. Ribó Chem. Soc. Rev. 39 2010 569 577
144. M.M. Green, B.A. Garetz, B. Muñoz, H.P. Chang, S. Hoke, and R.G. Cooks J. Am. Chem. Soc. 117 1995 4181 4182
145. M.M. Green, J.-W. Park, T. Sato, A. Teramoto, S. Lifson, R.L.B. Selinger, and J.V. Selinger Angew. Chem., Int. Ed. 38 1999 3138 3154
146. see also Ref. 3, Sect. 5.3.2., pp 86-88.
147. I. Weissbuch, L. Leiserowitz, and M. Lahav P. Walde, Prebiotic Chemistry, Topics in Current Chemistry Vol. 259 2005 Springer Berlin 123 165
148. I. Weissbuch, R.A. Illos, G. Bolbach, and M. Lahav Acc. Chem. Res. 42 2009 1128 1140 and references cited therein
149. For revisions on the chemistry of α-amino acid N-carboxyanhydrides: H.R. Kricheldorf Angew. Chem., Int. Ed. 45 2006 5752 5784
150. N. Hadjichristidis, H. Iatrou, M. Pitsikalis, and G. Sakellariou Chem. Rev. 109 2009 5528 5578
151. M.M. Green, and V. Jain Origins Life Evol. Biosphere 40 2010 111 118
152. G. Wald Ann. N.Y. Acad. Sci. 69 1957 352 368
153. A. Brack, and G. Spach Nature 229 1971 124 125
154. A. Brack, and G. Spach J. Mol. Evol. 15 1980 231 238
155. A. Brack, and G. Spach Origins Life 11 1981 135 142
156. A. Brack Origins Life Evol. Biosphere 17 1987 367 379
157. A. Brack Pure Appl. Chem. 65 1993 1143 1151
158. K. Tamura BioSystems 92 2008 91 98
159. For examples of stereoselective aminoacylation processes with racemic and d-amino acid derivatives: A.T. Profy, and D.A. Usher J. Am. Chem. Soc. 106 1984 5030 5031
160. J.C. Lacy Jr., N.S.M.D. Wickramasinghe, and R.S. Sabatini Experientia 48 1992 379 383
161. M. Di Giulio BioSystems 80 2005 175 184
162. R. Root-Bernstein BioEssays 29 2007 689 698
163. Green, M. M. Personal Communication (to P.C.).
164. A. Pross Chem. Eur. J. 15 2009 8374 8381
165. Eliot, T. S. The Complete Poems and Plays; Harcourt Brace & Co.: Orlando, FL, 1952; the quotation is from the poem Little Gidding (No. 4 of Four Quartets).