Racemization of Meteoritic Amino Acids

Icarus

Volumn 145, Issue 1, 2000, Pages 272-281

  Cohen, Barbara A ^a   Chyba, Christopher F ^b,c  

^a UNIVERSITY OF ARIZONA   (United States)

^b SETI INSTITUTE   (United States)

^c STANFORD UNIVERSITY   (United States)

Author keywords

Exobiology; Meteorites; Organic chemistry; Prebiotic chemistry; Prebiotic environments

Indexed keywords

EID: 0000539654     PISSN: 00191035     EISSN: None     Source Type: Journal    
DOI: 10.1006/icar.1999.6328     Document Type: Article

References (53)

1. Bada J. L. Kinetics of the nonbiological decomposition and racemization of amino acids in natural waters. Adv. Chem. Ser. 106:1971;309-331.
2. Bada J. L. Kinetics of racemization of amino acids as a function of pH. J. Am. Chem. Soc. 94:1972;1371-1373.
3. Bada J. L. Amino acid racemization dating of fossil bones. Annu. Rev. Earth Planet. Sci. 13:1985a;241-268.
4. Bada, J. L.1985b. Racemization of amino acids. In Chemistry and Biochemistry of the Amino AcidsG. C. Barrett, Ed., pp. 399-414. Chapman and Hall, London.
5. Bada J. L. Amino acid cosmogeochemistry. Phil. Trans. R. Soc. London B. 333:1991;349-358.
6. Bada J. L., McDonald G. D. Amino acid racemization on Mars: Implications for the preservation of biomolecules from an extinct martian biota. Icarus. 114:1995;139-143.
7. Bada J. L., Schroeder R. A. Racemization of isoleucine in calcareous marine sediments: Kinetics and mechanism. Earth Planet. Sci. Lett. 15:1972;1-11.
8. Bada J. L., Wang X. S., Poinar H. N., Paabo S., Poinar G. O. Amino acid racemization in amber-entombed insects: Implications for DNA preservation. Geochim. Cosmochim. Acta. 58:1994;3131-3135.
9. Bailey J., Chrysostomou A., Hough J. H., Gledhill T. M., McCall A., Clark S., Menard F., Tamura M. Circular polarization in star-formation regions: Implications for biomolecular homochirality. Science. 281:1998;672-674.
10. Bonner W. A. The origin and amplification of biomolecular chirality. Origins Life Evol. Biosphere. 21:1991;59-111.
11. Bunch T. E., Chang S. Carbonaceous Chondrites. II. Carbonaceous chondrite phyllosilicates and light element geochemistry as indicators of parent body processes and surface conditions. Geochim. Cosmochim. Acta. 44:1980;1543-1577.
12. Caffee M. W., Nishiizumi K. Exposure ages of carbonaceous chondrites. II. Meteoritics Planet. Sci. 32:1997;A26.
13. Caffee, M. W., J. N. Goswami, C. M. Hohenberg, K. Marti, and R. C. Reedy1988. Irradiation records in meteorites. In Meteorites and the Early Solar SystemJ. F. Kerridge and M. S. Matthews, Eds., pp. 205-245. Univ. of Arizona Press, Tucson.
14. Cassen P. Utilitarian models of the solar nebula. Icarus. 112:1994;405-429.
15. Chyba C. F. Extraterrestrial amino acids and terrestrial life. Nature. 348:1990;113-114.
16. Chyba C. F. A left-handed Solar System? Nature. 389:1997;234-235.
17. Chyba C. F., Sagan C. Endogeneous production, exogeneous delivery, and impact-shock synthesis of organic molecules: An inventory for the origins of life. Nature. 355:1992;125-132.
18. Clayton R. N., Mayeda T. K. The oxygen isotope record in Murchison and other carbonaceous chondrites. Earth Planet. Sci. Lett. 67:1984;151-161.
19. Cline, D. B.1996. On the determination of the physical origin of homochirality in life. In Chemical Evolution: Physics of the Origin and Evolution of LifeJ. Chela-Flores and F. Raulin, Eds., pp. 251-267. Kluwer Academic, The Netherlands.
20. Cooper G. W., Cronin J. R. Linear and cyclic aliphatic carboxamides of the Murchison meteorite: Hydrolyzable derivatives of amino acids and other carboxylic acids. Geochim. Cosmochim. Acta. 59:1995;1003-1015.
21. Cronin J. R. Acid-labile amino acid precursors in the Murchison meteorite. 1. Chromatographic Fractionation. Origins Life. 7:1976;337-342.
22. Cronin J. R., Pizzarello S. Enantiomeric excesses in meteoric amino acids. Science. 275:1997;951-952.
23. Cronin, J. R., W. E. Gandy, and S. Pizzarello1980. Amino acids of the Murchison meteorite. In Biogeochemistry of Amino AcidsP. E. Hare, T. C. Hoering, and K. King, Jr., Eds., pp. 145-168. Wiley, New York.
24. DuFresne E. R., Anders E. On the chemical evolution of the carbonaceous chondrites. Geochim. Cosmochim. Acta. 26:1962;1085-1114.
25. Dungworth, G., N. J. Vincken, and A. W. Schwartz1974. Racemization of aliphatic amino acids in fossil collagen of Pleistocene, Pliocene, and Miocene ages. In Advances in Organic ChemistryB. Tissot and F. Bienner, Eds., pp. 689-700. Editions Technip, Paris.
26. Engel M. H., Macko S. A. Isotopic evidence for extraterrestrial non-racemic amino acids in the Murchison meteorite. Nature. 389:1997;265-268.
27. Flores J. J., Bonner W. A., Massey G. A. Asymmetric photolysis of (RS)-leucine with circularly polarized ultraviolet light. J. Am. Chem. Soc. 99:1977;3622-3624.
28. Grimm R. E., McSween H. Y. Jr. Water and the thermal evolution of carbonaceous chondrite parent bodies. Icarus. 82:1989;244-280.
29. Jacques J., Collet A., Wilen S. H. Enantiomers, Racemates, and Resolutions. 1981.
30. Kvenvolden K., Lawless J., Pering K., Peterson E., Flores J., Ponnamperuma C., Kaplan I. R., Moore C. Evidence for extraterrestrial amino-acids and hydrocarbons in the Murchison meteorite. Nature. 228:1970;923-926.
31. Lerner N. R. Influence of Murchison or Allende minerals on hydrogen-deuterium exchange of amino acids. Geochim. Cosmochim. Acta. 59:1995;1623-1631.
32. Lerner N. R., Peterson E., Chang S. The Strecker synthesis as a source of amino acids in carbonaceous chondrites: Deuterium retention during synthesis. Geochim. Cosmochim. Acta. 57:1993;4713-4723.
33. Mason S. F. Origins of the handedness of biological molecules. Biological Symmetry and Handedness. 1991;3-15.
34. Norden B. Was photoresolution of amino acids the origin of optical activity in life? Nature. 266:1977;567-568.
35. Peltzer E. T., Bada J. L., Schlesinger G., Miller S. L. The chemical conditions on the parent body of the Murchison meteorite: Some conclusions based on amino, hydroxy and dicarbolic acids. Adv. Space Res. 4:1984;69-74.
36. Pendleton Y. J., Sandford S. A., Allamandola L. J., Tielens A. G. G. M., Sellgren K. Near-infrared absorption spectroscopy of interstellar hydrocarbon grains. Astrophys. J. 437:1994;683-696.
37. Pierazzo E., Chyba C. F. Amino acid survival in large cometary impacts. Meteoritics Planet. Sci. 34:1999;909-918.
38. Pizzarello S., Cronin J. R. Alanine enantiomers in the Murchison meteorite. Nature. 394:1998;236.
39. Rodante F. Thermodynamics and kinetics of decomposition processes for standard α-amino acids and some of their dipeptides in the solid state. Thermochim. Acta. 200:1992;47-60.
40. Schroeder R. A. Kinetics, Mechanism, and Geochemical Application of Amino Acid Racemization in Various Fossils. 1974.
41. Scott, E. R. D., G. J. Taylor, H. E. Newsom, F. Herbert, M. Zolensky, and J. F. Kerridge1989. Chemical, thermal, and impact processing of asteroids. In Asteroids IIR. P. Binzel, T. Gehrels, and M. S. Matthews, Eds., pp. 701-739. Univ. of Arizona Press, Tucson.
42. Shimoyama A., Harada K., Yanai K. Amino acids from the Yamato-791198 carbonaceous chondrite from Antarctica. Chem. Lett. 1985:1985;1183-1186.
43. Shock E. L., Schulte M. D. Summary and implications of reported amino acid concentrations in the Murchison meteorite. Geochim. Cosmochim. Acta. 54:1990;3159-3173.
44. Shou M. Y. Kinetics and Mechanisms of Several Amino Acid Diagenetic Reactions in Aqueous Solutions and in Fossils. 1979.
45. Sivakua T. Structural Effects on the Kinetics and Mechanism of the Racemization of Arylglycines. 1978.
46. Smith, G. G., and R. C. Evans1980. The effects of structure and conditions on the rate of racemization of free and bound amino acids. In Biogeochemistry of Amino AcidsP. E. Hare, T. C. Hoering, and K. King, Jr., Eds., pp. 257-282. Wiley, New York.
47. Smith G. G., Reddy G. V. Effect of the side chain on the racemization of amino acids in aqueous solution. J. Org. Chem. 54:1989;4529-4535.
48. Wilson H., Cannan R. K. The glutamic acid-pyrrolidonecarboxylic acid system. J. Biol. Chem. 119:1937;309-331.
49. Wonnacott, D. M. 1979, The Application of Gas Chromatography to the Resolution of Enantiomeric Mixtures of Amino Acids, Factors Affecting the Racemization of Amino Acids. Ph.D. thesis, Utah State University, Logan, UT.
50. Zinner E. Stellar nucleosynthesis and the isotopic composition of presolar grains from primitive meteorites. Annu. Rev. Earth Planet. Sci. 26:1998;147-188.
51. Zolensky, M., and H. Y. McSween1988. Aqueous alteration. In Meteorites and the Early Solar SystemJ. F. Kerridge and M. S. Matthews, Ed., pp. 114-143. Univ. of Arizona Press, Tucson.
52. Zolensky M. E., Bourcier W. L., Gooding J. L. Aqueous alteration on the hydrous asteroids: Results of EQ3/6 computer simulations. Icarus. 78:1989;411-425.
53. Zolensky M. E., Browning L. B. CM chondrites exhibit the complete petrologic range from type 2 to 1. Meteoritics. 29:1994;556.