Amplification of chirality at solid surfaces

Origins of Life and Evolution of Biospheres

Volumn 40, Issue 1, 2010, Pages 41-50

  Ernst, Karl Heinz ^a  

^a SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

Author keywords

Chiral amplification; Conglomerates; Scanning tunneling microscopy; Surface crystallography

Indexed keywords

ADSORPTION; AMPLIFICATION; CONGLOMERATE; CRYSTAL STRUCTURE; CRYSTALLIZATION; MOLECULAR ANALYSIS; SCANNING TUNNELLING MICROSCOPY; THREE-DIMENSIONAL MODELING; TWO-DIMENSIONAL MODELING;

COPPER;

ADSORPTION; ARTICLE; BIOGENESIS; CHEMISTRY; CRYSTALLIZATION; STEREOISOMERISM; SURFACE PROPERTY;

ADSORPTION; BIOGENESIS; COPPER; CRYSTALLIZATION; STEREOISOMERISM; SURFACE PROPERTIES;

EID: 77949410483     PISSN: 01696149     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11084-009-9185-2     Document Type: Article

References (45)

1. Addadi L, Berkovitch-Yellin Z, Weissbuch I, Lahav M, Leiserowitz L (1986) A link between macroscopic phenomena and molecular chirality: crystal as probes for the direct assignment of absolute configuration of chiral molecules. Top Stereochem 16: 1-85.
2. Barbosa LAMM, Sautet P (2001) Stability of chiral domains produced by adsorption of tartaric acid isomers on the Cu(110) surface: a periodic density functional theory study. J Am Chem Soc 123: 6639-6648.
3. Blackmond DG (2004) Asymmetric autocatalysis and its implications for the origin of homochirality. Proc Natl Acad Sci USA 101: 5732-5736.
4. Bonner WA (1988) Origins of chiral homogeneity in nature. Top Stereochem 18: 1-96.
5. Bürgi T, Urakawa A, Behzadi B, Ernst KH, Baiker A (2004) The absolute configuration of heptahelicene: a VCD spectroscopy study. New J Chem 28: 332-334.
6. Dunitz JD (1996) Symmetry arguments in chemistry. Proc Natl Acad Sci USA 93: 14260-14266.
7. Ernst KH (2006) Top Curr Chem 265: 209-252.
8. Ernst KH (2008) Amplification of chirality in two-dimensional molecular lattices. Curr Opin Colloid Interface Sci 13: 54-59.
9. Ernst KH, Schlatterbeck D, Christmann K (1999) Adsorption of carbon dioxide on Cu(110) and on hydrogen and oxygen covered Cu(110) surfaces. Phys Chem Chem Phys 1: 4105-4112.
10. Ernst KH, Kuster Y, Fasel R, Müller M, Ellerbeck U (2001) Two-dimensional separation of [7]helicene enantiomers on Cu(111). Chirality 13: 675-678.
11. Eschenmoser A (1999) Chemical etiology of nucleic acid structure. Science 284: 2118-2123.
12. 18 on copper surfaces: an x-ray photoelectron diffraction study. J Chem Phys 115: 1020-1027.
13. Fasel R, Parschau M, Ernst KH (2003) Angew Chem Int Ed 42: 5178-5181.
14. Fasel R, Wider J, Quitmann C, Ernst KH, Greber T (2004) Angew Chem Int Ed 43: 2853-2856.
15. Fasel R, Parschau M, Ernst KH (2006) Amplification of chirality in two-dimensional enantiomorphous lattices. Nature 439: 449-452.
16. Feringa BL, van Delden RA (1999) Absolute asymmetric synthesis: the origin, control, and amplification of chirality. Angew Chem Int Ed 38: 3418-3438.
17. Green MM, Reidy MP, Johnson RJ, Darling G, O'Leary DJ, Wilson G (1989) Macromolecular stereochemistry: the out-of-proportion influence of optically active comonomers on the conformational characteristics of polyisocyanates. The sergeants and soldiers experiment. J Am Chem Soc 111: 6452-6454.
18. Green MM, Garetz BA, Munoz B, Chang H, Hoke S, Cooks RG (1995) Majority rule in the copolymerization of mirror image isomers. J Am Chem Soc 117: 4181-4182.
19. Green MM, Park JW, Sato T, Teramoto A, Lifson S, Selinger RLB, Selinger JV (1999) The macromolecular route to chiral amplification. Angew Chem Int Ed 38: 3138-3154.
20. Humblot V, Ortega Lorenzo M, Baddeley CJ, Haq S, Raval R (2004) Local and global chirality at surfaces: succinic acid versus tartaric acid on Cu(110). J Am Chem Soc 126: 6460-6469.
21. Janoschek R (1991) Theories of the origin of biomolecular handedness. In: Chirality-from weak bosons to the a-helix. Springer, Heidelberg, pp 18-33.
22. Kahr B, Freudenthal JH (2008) Dendritic crystal growth, differential circular scattering, and the origin of biomolecular homochirality. Chirality 20: 973-977.
23. Luther A, Brandsch R, von Kiedrowski G (1998) Surface-promoted replication and exponential amplification of DNA analogues. Nature 396: 245-248.
24. Mason SF (1983) Molecular handedness and the origins of chiral discrimination. Int Rev Phys Chem 3: 217-241.
25. Merz L, Parschau M, Zoppi L, Baldridge KK, Siegel JS, Ernst KH (2009) Reversible phase transitions in a buckybowl monolayer. Angew Chem Int Ed 48: 1966-1969.
26. Orgel LE (2000) Self-organizing biochemical cycles. Proc Natl Acad Sci USA 97: 12503-12504.
27. Palmans ARA, Meijer EW (2007) Amplification of chirality in dynamic supramolecular aggregates. Angew Chem Int Ed 46: 8949-8968.
28. Parschau M, Romer S, Ernst KH (2004) Induction of homochirality in achiral enantiomorphous monolayers. J Am Chem Soc 126: 15398-15399.
29. Parschau M, Kampen T, Ernst KH (2005) Homochirality in monolayers of achiral meso tartaric acid. Chem Phys Lett 407: 433-437.
30. Parschau M, Behzadi B, Romer S, Ernst KH (2006) Stereoisomeric influence on 2D lattice structure: achiral meso-tartaric acid versus chiral tartaric acid. Surf Interface Anal 38: 1607-1610.
31. Parschau M, Fasel R, Ernst KH, Gröning O, Brandenberger L, Schillinger R, Greber T, Seitsonen A, Wu YT, Siegel JS (2007) Buckybowls on metal surfaces: symmetry mismatch and enantiomorphism of corannulene on Cu(110). Angew Chem Int Ed 46: 8258-8261.
32. Parschau M, Fasel R, Ernst KH (2008) Coverage and enantiomeric excess dependent enantiomorphism in two-dimensional molecular crystals. Cryst Growth Des 8: 1890-1896.
33. Podlech J (2001) Origin of organic molecules and biomolecular homochirality. Cell Mol Life Sci 58: 44-60.
34. Puchot C, Samuel O, Duñach E, Zhao S, Agami C, Kagan HB (1986) Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions. J Am Chem Soc 108: 2353-2357.
35. Romer S, Behzadi B, Fasel R, Ernst KH (2005) Homochiral conglomerates and racemic crystals in two dimensions: tartaric acid on Cu(110). Chem Eur J 11: 4149-4154.
36. Sato I, Kadowaki K, Soai K (2000) Asymmetric synthesis of an organic compound with high enantiomeric excess induced by inorganic sodium chlorate. Angew Chem Int Ed 39: 1510-1512.
37. Schipper PE, Harrowell PR (1983) A van der Waals model of chiral mixtures using a Chiral Lennard-Jones potential. Applications to the Pasteur Experiment and Phenomena in Chiral Solvents. J Am Chem Soc 105: 723-730.
38. Seiders TJ, Elliott EL, Grube GH, Siegel JS (1999) Synthesis of corannulene and alkyl derivatives of corannulene. J Am Chem Soc 121: 7804-7813.
39. Siegel JS (1998) Homochiral imperative of molecular evolution. Chirality 10: 24-27.
40. Soai K, Shibata T, Morioka H, Choji K (1995) Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule. Nature 378: 767-768.
41. Viedma C (2001) Enantiomeric crystallization from D, L-aspartic and D, L-glutamic acids: implications for biomolecular chirality in the origin of life. Orig Life Evol Biosph 31: 501-509.
42. Viedma C (2005) Chiral symmetry breaking during crystallization: complete chiral purity induced by nonlinear autocatalysis and recycling. Phys Rev Lett 94: 065504/1-4.
43. 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.
44. Welch CJ (2001) Formation of highly enantioenriched microenvironments by stochastic sorting of conglomerate crystals: a plausible mechanism for generation of enantioenrichment on the prebiotic earth. Chirality 13: 425-427.
45. Zepik H, Shavit E, Tang M, Jensen TR, Kjaer K, Bolbach G, Leiserowitz L, Weissbuch I, Lahav M (2002) Chiral amplification of oligopeptides in two-dimensional crystalline self-assemblies on water. Science 295: 1266-1269.