On the origin of single chirality of amino acids and sugars in biogenesis

Accounts of Chemical Research

Volumn 45, Issue 12, 2012, Pages 2045-2054

  Hein, Jason E ^a,b   Blackmond, Donna G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBOHYDRATE; FORMALDEHYDE; GLYCERALDEHYDE; PREBIOTIC AGENT; RNA;

ARTICLE; ASTRONOMY; BIOGENESIS; CHEMISTRY; KINETICS; METABOLISM; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; BIOGENESIS; CARBOHYDRATES; EVOLUTION, CHEMICAL; FORMALDEHYDE; GLYCERALDEHYDE; KINETICS; PREBIOTICS; RNA; STEREOISOMERISM;

EID: 84871289747     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar200316n     Document Type: Article

References (44)

1. Eschenmoser, A. The Search For the Chemistry of Life's Origin Tetrahedron 2007, 63, 12821-12844
2. Calvin, M. Molecular Evolution; Oxford University Press: Oxford, U.K., 1969.
3. Frank, F. C. On Spontaneous Asymmetric Synthesis Biochim. Biophys. Acta 1953, 11, 459-463
4. Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Asymmetric Autocatalysis and Amplification of Enatiomeric Excess of a Chiral Molecule Nature 1995, 378, 767-768
5. Blackmond, D. G.; McMillan, C. R.; Ramdeehul, S.; Schorm, A.; Brown, J. M. Origins of Asymmetric Amplification in Autocatalytic Alkylzinc Additions J. Am. Chem. Soc. 2001, 123, 10103-10104
6. Klussmann, M.; Iwamura, H.; Mathew, S. P.; Wells, D. H.; Pandya, U., Jr.; Armstrong, A.; Blackmond, D. G. Thermodynamic Control of Asymmetric Amplification in Amino Acid Catalysis Nature 2006, 441, 621-623
7. Viedma, C.; Ortiz, J. E.; de Torres, T.; Izumi, T.; Blackmond, D. G. Evolution of Solid Phase Homochirality for a Proteinogenic Amino Acid J. Am. Chem. Soc. 2008, 130, 15274-15275
8. Blackmond, D. G. Asymmetric Autocatalysis and Its Implications for the Origin of Homochirality Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5732-5736
9. Blackmond, D. G. The Origin of Biological Homochirality Cold Spring Harbor Perspect. Biol. 2010, 2 a002147
10. Butlerov, A. M. Formation Synthétique D'Une Substance Sucreé C. R, Acad. Sci. 1861, 53, 145-147
11. Breslow, R. On the Mechanism of the Formose Reaction Tetrahedron Lett. 1959, 21, 22-26
12. Miller, S. L. Which Organic Compounds Could Have Occurred on the Prebiotic Earth? Cold Spring Harbor Symp. Quant. Biol. 1987, 52, 17-27
13. Benner, S. A.; Kim, H.-J.; Yang, Z. Setting the Stage: The History, Chemistry, and Geobiology Behind RNA Cold Spring Harbor Perspect. Biol. 2010, 2 a003541
14. Breslow, R.; Cheng, Z.-L. L-Amino Acids Catalyze the Formation of an Excess of D-Glyceraldehyde, and Thus of Other D Sugars, Under Credible Prebiotic Conditions Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 5723-5725
15. Blackmond, D. G.; Moran, A.; Hughes, M.; Armstrong, A. Unusual Reversal of Enantioselectivity in the Proline-Mediated α-Amination of Aldehydes Induced by Tertiary Amine Additives J. Am. Chem. Soc. 2010, 132, 7598-7599
16. Hein, J. E.; Bures, J.; Lam, Y.-H.; Hughes, M.; Houk, K. N.; Armstrong, A.; Blackmond, D. G. Enamine Carboxylates as Stereodefining Intermediates in Prolinate Catalysis Org. Lett. 2011, 13, 5644-5647
17. Hein., J. E.; Blackmond, D. G. Unpublished results.
18. Pizzarello, S. The Chemistry of Life's Origin: A Carbonaceous Meteorite Perspective Acc. Chem. Res. 2006, 39, 231-237
19. Glavin, D. P.; Dworkin, J. P. Enrichment of the Amino Acid L-Isovaline by Aqueous Alteration on Cl and CM Meteorite Parent Bodies Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 5487-5492
20. Levine, M.; Kenesky, C. S.; Mazori, D.; Breslow, R. Enantioselective Synthesis and Enantiomeric Amplification of Amino Acids Under Prebiotic Conditions Org. Lett. 2008, 10, 2433-2436
21. Gilbert, W. The RNA World Nature 1986, 319, 818
22. Woese, C. The Genetic Code; Harper and Row, 1967; pp 179-195.
23. Cech, T. R. The RNA World in Context Cold Spring Harbor Perspect. Biol. 2011, 10.1101/cshperspect.a006742
24. Powner, M. W.; Gerland, B.; Sutherland, J. D. Synthesis of Activated Pyrimidine Ribonucleotides In Prebiotically Plausible Conditions Nature 2009, 459, 239-242
25. Powner, M. W.; Sutherland, J. D.; Szostak, J. W. Chemoselective Multicomponent One-Pot Assembly of Purine Precursors in Water J. Am. Chem. Soc. 2010, 132, 16677-16688
26. Schrum, J. P.; Zhu, T. F.; Szostak, J. W. The Origins of Cellular Life. RNA Worlds; Atkins, J. F.; Gesteland, R. F.; Cech, T. R., Eds.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 2010.
27. Powner, M. W.; Sutherland, J. D. Phosphate-Mediated Interconversion of Ribo- and Arabino-Configured Prebiotic Nucleotide Intermediate Angew. Chem., Int. Ed. 2010, 49, 4641-4643
28. Hein, J. E.; Tse, E.; Blackmond, D. G. A Route to Enantiopure RNA Precursors From Nearly Racemic Starting Materials Nat. Chem. 2011, 3, 704-706
29. Anastasi, C.; Crowe, M. A.; Powner, M. W.; Sutherland, J. D. Direct Assembly of Nucleoside Precursors From Two- And Three-Carbon Units Angew. Chem., Int. Ed. 2006, 45, 6176-6179
30. Bonner, W. A. Origins of Chiral Homogeneity in Nature Top. Stereochem. 1988, 18, 1-96
31. Balavoine, G.; Moradpour, A.; Kagan, H. B. Preparation of Chiral Compounds with High Optical Purity by Irradiation with Circularly Polarized Light, a Model Reaction for the Prebiotic Generation of Optical Activity J. Am. Chem. Soc. 1974, 96, 5152-5158
32. Flores, J. J.; Bonner, W. A.; Massey, G. A. Asymmetric Photolysis of (rs)-Leucine With Circularly Polarized Ultraviolet Light J. Am. Chem. Soc. 1977, 99, 3622-3625
33. Morowitz, H. A Mechanism for the Amplification of Fluctuations in Racemic Mixtures J. Theor. Biol. 1969, 25, 491-494
34. Klussmann, M.; White, A. J. P.; Armstrong, A; Blackmond, D. G. Rationalization and Prediction of Solution Enantiomeric Excess in Ternary Phase Systems Angew. Chem., Int. Ed. 2006, 47, 7985-7989
35. Klussmann, M.; Izumi, T.; White, A. J. P.; Armstrong, A.; Blackmond, D. G. Emergence of Solution-Phase Homochirality via Crystal Engineering of Amino Acids J. Am. Chem. Soc. 2007, 123, 7657-7660
36. Breslow, R.; Levine, M. Amplification of Enantiomeric Concentrations under Credible Prebiotic Conditions Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 12979-12980
37. Breslow, R.; Levine, M.; Cheng, Z.-L. Imitating Prebiotic Homochirality on Earth Orig. Life Evol. Biospheres 2010, 40, 11-26
38. Weissbuch, I.; Lahav, M. Crystalline Architectures as Templates of Relevance to the Origins of Homochirality Chem. Rev. 2011, 111, 3236-3267
39. Weissbuch, I.; Addadi, L.; Berkovitch-Yellin, Z.; Gati, E.; Lahav, M.; Leiserowitz, L. Spontaneous Generation and Amplification of Optical Activity in a-Amino Acids by Enantioselective Occlusion into Centrosymmetric Crystals of Glycine Nature 1984, 310, 161-164
40. Illos, R. A.; Bisogno, F. R.; Clodic, G.; Bolbach, G.; Weissbuch, I.; Lahav, M. Oligopeptides and Copeptides of Homochiral Sequence, via β-Sheets, from Mixtures of Racemic α-Amino Acids, in a One-Pot Reaction in Water; Relevance to Biochirogenesis J. Am. Chem. Soc. 2008, 130, 8651-8659
41. Haq, S.; Liu, N.; Humblot, V.; Hansen, A. P. J.; Raval, R. Drastic Symmetry Breaking in Supramolecular Organization of Enantiomerically Unbalanced Monolayers at Surfaces Nat. Chem. 2009, 1, 409-414
42. Green, M. M.; Cheon, K.-S.; Yang, S.-Y.; Park, J.-W.; Swansburg, A.; Liu, W. Chiral Studies Across the Spectrum of Polymer Science Acc. Chem. Res. 2001, 34, 672-680
43. Cantekin, S.; Blakenende, D. W. R.; Smulders, M. J.; Palmans, A. R. A.; Meijer, E. W. The Effect of Isotopic Substitution on the Chirality of a Self-assembled Helix Nat. Chem. 2009, 3, 42-46
44. Budin, I.; Szostak, J. W. Expanding Roles For Diverse Physical Phenomena During the Origin of Life Annu. Rev. Biophys. 2010, 39, 245-263