Emergence of homochirality in far-from-equilibrium systems: mechanisms and role in prebiotic chemistry.

Since the model proposed by Frank (Frank FC, Biochem Biophys Acta 1953;11:459-463), several alternative models have been developed to explain how an asymmetric non-racemic steady state can be reached by a chirally symmetric chemical reactive system. This paper explains how a stable non-racemic regime can be obtained as a symmetry breaking occurring in a far-from-equilibrium reactive system initiated with an initial imbalance. Departing from the variations around the original Frank's model that are commonly described in the literature, i.e. open-flow systems of direct autocatalytic reactions, we discuss recent developments emphasizing both an active recycling of components and an autocatalytic network of simple reactions. We will present our APED model as the most natural realization of such thermodynamic openness and non-equilibrium, of recycling and of network autocatalysis, each of these in prebiotic conditions. The different experimental and theoretical models in the literature will be classified according to mechanism. The place and role of such self-structured networks responsible for the presence of homochirality in the primitive Earth will be detailed.

[1]  A. Passalacqua,et al.  Parity Violation Energy Of Biomolecules – I: Polypeptides , 2005, Origins of Life and Evolution of Biospheres.

[2]  G. Nicholson,et al.  Parity Violating Energetic Difference and Enantiomorphous Crystalsp-Caveats; Reinvestigation of Tyrosine Crystallization , 2006, Origins of Life and Evolution of Biospheres.

[3]  E. I. Klabunovskii Can enantiomorphic crystals like quartz play a role in the origin of homochirality on earth? , 2001, Astrobiology.

[4]  F. Frank,et al.  On spontaneous asymmetric synthesis. , 1953, Biochimica et biophysica acta.

[5]  W. Bonner Chirality Amplification – The Accumulation Principle Revisited , 1999, Origins of life and evolution of the biosphere.

[6]  D. Kondepudi,et al.  A new perspective on the mechanism of asymmetric amplification , 2005 .

[7]  L. Keszthelyi,et al.  Unconsidered sources of chirality in nature , 1981, Origins of life.

[8]  G. Tranter,et al.  The electroweak origin of biomolecular handedness , 1985, Proceedings of the Royal Society of London. A. Mathematical and Physical Sciences.

[9]  K. Ruiz-Mirazo,et al.  A Universal Definition of Life: Autonomy and Open-Ended Evolution , 2004, Origins of life and evolution of the biosphere.

[10]  P. Cintas Elementary asymmetry and biochirality: no longer twinned. , 2001, Chemphyschem : a European journal of chemical physics and physical chemistry.

[11]  Laurent Nahon,et al.  Asymmetric vacuum UV photolysis of the amino acid leucine in the solid state. , 2005, Angewandte Chemie.

[12]  Sato,et al.  The Macromolecular Route to Chiral Amplification. , 1999, Angewandte Chemie.

[13]  Cristobal Viedma,et al.  Chiral symmetry breaking during crystallization: complete chiral purity induced by nonlinear autocatalysis and recycling. , 2004, Physical review letters.

[14]  J. Siegel Homochiral imperative of molecular evolution , 1998 .

[15]  J. McBride,et al.  Spontaneous Resolution by Stirred Crystallization , 1991 .

[16]  R. Tauler,et al.  Indications towards a stereoselectivity of the salt-induced peptide formation reaction , 2004 .

[17]  V. Goldanskii,et al.  Homochirality and stereospecific activity: evolutionary aspects. , 1991, Bio Systems.

[18]  H. Hyuga,et al.  Chirality selection in open flow systems and in polymerization , 2005, physics/0503057.

[19]  Kenso Soai,et al.  Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule , 1995, Nature.

[20]  Elchanan Mossel,et al.  Random biochemical networks: the probability of self-sustaining autocatalysis. , 2005, Journal of theoretical biology.

[21]  J. Podlech Origin of organic molecules and biomolecular homochirality , 2001, Cellular and Molecular Life Sciences CMLS.

[22]  Hugues Bersini,et al.  Recycling Frank: Spontaneous emergence of homochirality in noncatalytic systems. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[23]  K. Iwamoto Spontaneous appearance of chirally asymmetric steady states in a reaction model including Michaelis?Menten type catalytic reactions , 2003 .

[24]  Thomas Buhse,et al.  Mirror-symmetry breaking in the Soai reaction: a kinetic understanding. , 2005, Proceedings of the National Academy of Sciences of the United States of America.

[25]  P. Luisi,et al.  Chiral amplification of oligopeptides in the polymerization of α-amino acid N-carboxyanhydrides in water , 2003 .

[26]  John M. Brown,et al.  Asymmetric autocatalysis: novel structures, novel mechanism? , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[27]  Kenso Soai,et al.  Spontaneous absolute asymmetric synthesis in the presence of achiral silica gel in conjunction with asymmetric autocatalysis. , 2006, Chirality.

[28]  F. Selsis,et al.  Featured Article Prebiotic synthesis of sequential peptides on the Hadean beach by a molecular engine working with nitrogen oxides as energy sources , 2002 .

[29]  Akira Sasaki,et al.  Noisy clues to the origin of life , 2002, Proceedings of the Royal Society of London. Series B: Biological Sciences.

[30]  R. Cooks,et al.  Chiral enrichment of serine via formation, dissociation, and soft-landing of octameric cluster ions , 2004, Journal of the American Society for Mass Spectrometry.

[31]  P. Luisi Contingency and determinism. , 2003, Philosophical transactions. Series A, Mathematical, physical, and engineering sciences.

[32]  D. Kondepudi,et al.  Chiral Symmetry Breaking in Sodium Chlorate Crystallizaton , 1990, Science.

[33]  M. Steel,et al.  Detecting Autocatalytic, Self-sustaining Sets in Chemical Reaction Systems , 2003 .

[34]  P. Decker Possible resolution of racemic mixtures by bistability in “bioids”, open systems which can exist in several steady states , 2005, Journal of Molecular Evolution.

[35]  Spontaneous appearance of chirally asymmetric steady states in a reaction model including imperfectly stereoselective, chirally autocatalytic reactions , 2002 .

[36]  D. Kondepudi,et al.  Chiral autocatalysis, spontaneous symmetry breaking, and stochastic behavior. , 2001, Accounts of chemical research.

[37]  Peter Schuster,et al.  A principle of natural self-organization , 1977, Naturwissenschaften.

[38]  K. Soai,et al.  Enantioselective automultiplication of chiral molecules by asymmetric autocatalysis. , 2000, Accounts of Chemical Research.

[39]  K. Soai,et al.  Asymmetric autocatalysis and the origin of chiral homogeneity in organic compounds. , 2001, Chemical record.

[40]  S. Kauffman Autocatalytic sets of proteins. , 1986 .

[41]  D. Deamer,et al.  Unexpected Differences between D- and L- Tyrosine Lead to Chiral Enhancement in Racemic Mixtures Dedicated to the memory of Prof. Shneior Lifson – A great liberal thinker. , 2002, Origins of life and evolution of the biosphere.

[42]  D. Kondepudi,et al.  Probability distributions of enantiomeric excess in unstirred and stirred crystallization of 1,1'-binaphthyl melt. , 2002, Chirality.

[43]  P. Schmidt Evolution of Homochirality by Epimerization of Random Peptide Chains. A Stochastic Model , 2006, Origins of Life and Evolution of Biospheres.

[44]  D. Blackmond,et al.  Asymmetric autocatalysis and its implications for the origin of homochirality , 2004 .

[45]  Mike A. Steel The emergence of a self-catalysing structure in abstract origin-of-life models , 2000, Appl. Math. Lett..

[46]  R. Shapiro Small Molecule Interactions were Central to the Origin of Life , 2006, The Quarterly Review of Biology.

[47]  W. Bonner,et al.  Parity violation and the evolution of biomolecular homochirality. , 2000, Chirality.

[48]  Q. Meng,et al.  Spontaneous resolution of silver double helicates consisting of achiral ligands with several aromatic rings. , 2006, Chemical communications.

[49]  I. Weissbuch,et al.  Stochastic "Mirror Symmetry Breaking" via Self-Assembly, Reactivity and Amplification of Chirality: Relevance to Abiotic Conditions , 2005 .

[50]  A. R. Hochstim Nonlinear mathematical models for the origin of asymmetry in biological molecules , 1975, Origins of life.

[51]  S. Solomon,et al.  The importance of being discrete: life always wins on the surface. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[52]  Y. Yamagata,et al.  Formation of cyanate and carbamyl phosphate by electric discharges of model primitive gas , 1982, Origins of life.

[53]  G. W. Nelson,et al.  Chiral-symmetry breaking in nonequilibrium systems , 1983 .

[54]  H. Hyuga,et al.  Complete Homochirality Induced by Nonlinear Autocatalysis and Recycling , 2003, physics/0310142.

[55]  G. Bolbach,et al.  Chiral Amplification of Oligopeptides via Polymerization in Two-dimensional Crystallites on Water , 2004, Origins of life and evolution of the biosphere.

[56]  R. Cooks,et al.  Serine octamers: cluster formation, reactions, and implications for biomolecule homochirality. , 2006, Angewandte Chemie.

[57]  W. Bonner,et al.  Experiments of the amplification of optical activity , 1980, Origins of life.

[58]  P. Cintas,et al.  From parity to chirality: chemical implications revisited† , 2000 .

[59]  P. Sandars A Toy Model for the Generation of Homochirality during Polymerization , 2003, Origins of life and evolution of the biosphere.

[60]  I. Gridnev Chiral Symmetry Breaking in Chiral Crystallization and Soai Autocatalytic Reaction , 2006 .

[61]  P. Decker The origin of molecular asymmetry through the amplification of “stochastic information” (noise) in bioids, open systems which can exist in several steady states , 1974, Journal of Molecular Evolution.

[62]  W. Bonner,et al.  The origin and amplification of biomolecular chirality , 2005, Origins of life and evolution of the biosphere.