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Amino Acids and the Asymmetry of Life

Published online by Cambridge University Press:  30 April 2013

Uwe J. Meierhenrich
Uwe J. Meierhenrich*
Affiliation:
University of Nice-Sophia Antipolis, Faculty of Sciences, UMR 7272 CNRS, Parc Valrose, 28 Avenue Valrose, France. E-mail: Uwe.Meierhenrich@unice.fr
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Abstract

‘How did life start on Earth?’ and ‘Why were left-handed amino acids selected for the architecture of proteins?’ A new attempt to answer these questions of high public and interdisciplinary scientific interest will be provided by this review. It will describe most recent experimental data on how the basic and molecular building blocks of life, amino acids, formed in a prebiotic setting. Most amino acids are chiral, that is that they cannot be superimposed with their mirror image molecules (enantiomers). In processes triggering the origin of life on Earth, the equal occurrence, i.e. the parity between left-handed amino acids and their right-handed mirror images, was violated. In the case of amino acids, the balance was tipped to the left – as a result of which life's proteins today exclusively implement the left-handed form of amino acids, called l-amino acid enantiomers. Neither plants, nor animals, including humans, make use of d-amino acids for the molecular architecture of their proteins (enzymes). This review addresses the molecular asymmetry of amino acids in living organisms, namely the preference for left-handedness. What was the cause for the violation of molecular parity of amino acids in the emergence of life on Earth? All the fascinating models proposed by physicists, chemists, and biologists will be vividly presented including the scientific conflicts. Special emphasis will be given to amino acid enantiomers that were subjected to chiral photons. The interaction between racemic molecules and chiral photons was shown to produce an enantiomeric enrichment that will be discussed in the context of absolute asymmetric synthesis. The concluding paragraphs will describe the attempt to verify any of those models with the chirality-module of the Rosetta mission. This European space mission contains probe Philae that was launched on board the Rosetta spacecraft with the aim of landing on the icy surface of comet 67P/Churyumov-Gerasimenko and analysing whether chiral organic compounds are present that could have been brought to the Earth by comet impacts.

Type
Focus: The Temptations of Chemistry
Information
European Review , Volume 21 , Issue 2 , May 2013 , pp. 190 - 199
Copyright
Copyright © Academia Europaea 2013

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References

References and Notes

1.Cline, D.B. (2005) On the physical origin of the homochirality of life. European Review, 13(suppl. S2), 49–59.CrossRefGoogle Scholar
2.Greenberg, J.M. (1993) Physical and chemical composition of comets – from interstellar space to the Earth. In: J.M. Greenberg (Ed.) The Chemistry of Life's Origins (The Netherlands: Kluwer Academic Publishers), pp. 195–197.CrossRefGoogle Scholar
3.Muñoz Caro, G.M., Meierhenrich, U.J., Schutte, W.A., Barbier, B., Arcones Segovia, A., Rosenbauer, H., Thiemann, W.H.-P., Brack, A. and Greenberg, J.M. (2002) Amino acids from ultraviolet irradiation of interstellar ice analogues. Nature, 416, 403–406.CrossRefGoogle ScholarPubMed
4.Bredehöft, J.H. and Meierhenrich, U.J. (2008) Amino acid structures from UV irradiation of simulated interstellar ices. In: N. Takenaka (Ed.) Recent developments of chemistry and photochemistry in ice (Kerala, India: Transworld Research Network), pp. 175–202.Google Scholar
5.Meierhenrich, U.J., Muñoz Caro, G.M., Bredehöft, J.H., Jessberger, E.K. and Thiemann, W.H.-P. (2004) Identification of diamino acids in the Murchison meteorite. Proceedings of the National Academy of Sciences USA, 101, 9182–9186.CrossRefGoogle ScholarPubMed
6.Gilbert, W. (1986) Origin of life: the RNA world. Nature, 319, 618.CrossRefGoogle Scholar
7.Nielsen, P.E., Egholm, M., Berg, R.H. and Buchardt, O. (1991) Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide. Science, 254, 1497–1500.CrossRefGoogle ScholarPubMed
8.Nielsen, P.E. (1993) Peptide nucleic acid (PNA): a model structure for the primordial genetic material. Origins of Life and Evolution of Biospheres, 23, 323–327.CrossRefGoogle Scholar
9.Bailey, J., Chrysostomou, A., Hough, J.H., Gledhill, T.M., McCall, A., Clark, S., Ménard, F. and Tamura, M. (1998) Circular polarization in star-formation regions: implications for biomolecular homochirality. Science, 281, 672–674.CrossRefGoogle ScholarPubMed
10.Buschermöhle, M., Whittet, D.C.B., Chysostomou, A., Hough, J.H., Lucas, P.W., Adamson, A.J., Whitney, B.A. and Wolff, M.J. (2005) An extended search for circularly polarized infrared radiation from the OMC-1 region of orion. Astrophysical Journal, 624, 821–826.CrossRefGoogle Scholar
11.Kuhn, W. and Braun, E. (1929) Photochemische Erzeugung optisch aktiver Stoffe. Die Naturwissenschaften, 17, 227–228.CrossRefGoogle Scholar
12.Balavoine, G., Moradpour, A. and Kagan, H.B. (1974) Preparation of chiral compounds with high optical purity by irradiation with circularly polarized light, a model reaction for the prebiotic generation of optical activity. Journal of the American Chemical Society, 96, 5152–5158.CrossRefGoogle Scholar
13.Flores, J.J., Bonner, W.A. and Massey, G.A. (1977) Asymmetric photolysis of (RS)-leucine with circularly polarized ultraviolet light. Journal of the American Chemical Society, 99, 3622–3625.CrossRefGoogle ScholarPubMed
14.Glavin, D.P. and Dworkin, J.P. (2009) Enrichment of the amino acid l-isovaline by aqueous alteration on CI and CM meteorite parent bodies. Proceedings of the National Academy of Sciences USA, 106, 5487–5492.CrossRefGoogle ScholarPubMed
15.Griesbeck, A.G. and Meierhenrich, U.J. (2002) Asymmetric photochemistry and photochirogenesis. Angewandte Chemie International Edition, 41, 3147–3154.3.0.CO;2-V>CrossRefGoogle ScholarPubMed
16.Meierhenrich, U.J., Filippi, J.-J., Meinert, C., Bredehöft, J.H., Takahashi, J., Nahon, L., Jones, N.C. and Hoffmann, S.V. (2010) Circular dichroism of amino acids in the vacuum-ultraviolet region. Angewandte Chemie International Edition, 49, 7799–7802.CrossRefGoogle ScholarPubMed
17.Meierhenrich, U.J., Nahon, L., Alcaraz, C., Bredehöft, J.H., Hoffmann, S.V., Barbier, B. and Brack, A. (2005) Asymmetric vacuum UV photolysis of the amino acid leucine in the solid state. Angewandte Chemie International Edition, 44, 5630–5634.CrossRefGoogle ScholarPubMed
18.Meierhenrich, U.J., Filippi, J.-J., Meinert, C., Hoffmann, S.V., Bredehöft, J.H. and Nahon, L. (2010) Photolysis of rac-leucine with circularly polarized synchrotron radiation. Chemistry & Biodiversity, 7, 1651–1659.CrossRefGoogle ScholarPubMed
19.De Marcellus, P., Meinert, C., Nuevo, M., Filippi, J.-J., Danger, G., Deboffle, D., Nahon, L., le Sergeant d'Hendecourt, L. and Meierhenrich, U.J. (2011) Non racemic amino acid production by ultraviolet irradiation of achiral interstellar ice analogs with circularly polarized light. Astrophysical Journal Letters, L27, 727.Google Scholar
20.Goesmann, F., Rosenbauer, H., Roll, R., Szopa, C., Raulin, F., Sternberg, R., Israel, G., Meierhenrich, U.J., Thiemann, W. and Muñoz Caro, G.M. (2007) COSAC, the cometary sampling and composition experiment on Philae. Space Science Reviews, 128, 257–280.CrossRefGoogle Scholar
21.Yamagata, Y. (1966) A hypothesis for the asymmetric appearance of biomolecules on Earth. Journal of Theoretical Biology, 11, 495–498.CrossRefGoogle ScholarPubMed
22.MacDermott, A. (1995) Electroweak enantioselection and the origin of life. Origins of Life and Evolution of Biospheres, 25, 191–199.CrossRefGoogle ScholarPubMed
23.Quack, M. (2002) How important is parity violation for molecular and biomolecular chirality. Angewandte Chemie International Edition, 41, 4618–4630.CrossRefGoogle ScholarPubMed
[24]Darge, W., Laczko, I. and Thiemann, W. (1976) Stereoselectivity of β irradiation of d,l-tryptophan in aqueous solution. Nature, 261, 522–524.CrossRefGoogle ScholarPubMed
25.Bonner, W.A., Lemmon, R.M. and Noyes, H.P. (1978) β-Radiolysis of crystalline 14C-labeled amino acids. Journal of Organic Chemistry, 43, 522–524.CrossRefGoogle Scholar
26.Garay, A.S. and Ahlgren-Beckendorf, J.A. (1990) Differential interaction of chiral β-particles with enantiomers. Nature, 346, 451–453.CrossRefGoogle Scholar
27.Kondepudi, D.K., Kaufman, R.J. and Singh, N. (1990) Chiral symmetry breaking in sodium chlorate crystallization. Science, 250, 975–976.CrossRefGoogle Scholar
28.Rikken, G.L.J.A. and Raupach, E. (2000) Enantioselective magnetochiral photochemistry. Nature, 405, 932–935.CrossRefGoogle ScholarPubMed
29.Meierhenrich, U.J. (2008) Amino Acids and the Asymmetry of Life (Heidelberg, Germany: Springer-Verlag), pp. 185–198.CrossRefGoogle Scholar