Photochirogenesis: Photochemical models on the absolute asymmetric formation of amino acids in interstellar space

Physics of Life Reviews

Volumn 8, Issue 3, 2011, Pages 307-330

  Meinert, Cornelia ^a   de Marcellus, Pierre ^b   Le Sergeant d'Hendecourt, Louis ^b,c   Nahon, Laurent ^d   Jones, Nykola C ^e   Hoffmann, Søren V ^e   Bredehöft, Jan Hendrik ^f   Meierhenrich, Uwe J ^a  

^a UNIVERSITÉ CÔTE D'AZUR   (France)

^b UNIVERSITÉ PARIS SUD   (France)

^c CNRS   (France)

^d SYNCHROTRON SOLEIL   (France)

^e AARHUS UNIVERSITY   (Denmark)

^f UNIVERSITY OF BREMEN   (Germany)

Author keywords

Amino acids; Astrochemistry; Asymmetric photolysis; Enantioselective photosynthesis; Homochirality; Origin of life

Indexed keywords

ASTROCHEMISTRY; ASYMMETRIC PHOTOLYSIS; ENANTIOSELECTIVE; HOMOCHIRALITY; ORIGIN OF LIFE;

ANIMALS; CHIRALITY; ENANTIOMERS; LIGHT POLARIZATION; MOLECULES; PHOTOLYSIS; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

ANIMALIA;

AMINO ACID;

ANIMAL; ASTROBIOLOGY; BIOLOGICAL MODEL; CHEMISTRY; HUMAN; METABOLISM; MICROCLIMATE; PHOTOCHEMISTRY; RADIATION EXPOSURE; REVIEW; STEREOISOMERISM;

AMINO ACIDS; ANIMALS; EXOBIOLOGY; EXTRATERRESTRIAL ENVIRONMENT; HUMANS; MODELS, BIOLOGICAL; PHOTOCHEMICAL PROCESSES; STEREOISOMERISM;

EID: 80455154970     PISSN: 15710645     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.plrev.2011.08.005     Document Type: Review

References (212)

1. Meierhenrich U. Amino acids and the asymmetry of life 2008, Springer-Verlag, Berlin-Heidelberg, Germany.
2. Griesbeck A.G., Meierhenrich U.L. Asymmetric photochemistry and photochirogenesis. Angew Chem Int Ed 2002, 41:3147-3154.
3. Munoz Caro G.M., Meierhenrich U.J., Schutte W.A., Barbler B., Segovia A.A., Rosenbauer H., et al. Amino acids from ultraviolet irradiation of interstellar ice analogues. Nature 2002, 416:403-406.
4. Bernstein M.P., Dworkin J.P., Sandford S.A., Cooper G.W., Allamandola L.J. Racemic amino acids from the ultraviolet photolysis of interstellar ice analogues. Nature 2002, 416:401-403.
5. Meierhenrich U.J., Caro G.M.M., Bredehoft J.H., Jessberger E.K., Thiemann W.H.P. Identification of diamino acids in the Murchison meteorite. Proc Natl Acad Sci 2004, 101:9182-9186.
6. Kuhn W., Braun E. Photochemical preparation of optically active substances. Naturwissenschaften 1929, 17:227-228.
7. Kuhn W., Knopf E. The preparation of optically active compounds by the aid of light. Z Physik Chem 1930, 7:292-310.
8. Kuhn W., Knopf E. Photochemical preparation of optically active substances. Naturwissenschaften 1930, 18:183.
9. Inoue Y. Asymmetric photochemical reactions in solution. Chem Rev 1992, 92:741-770.
10. Rhodes W., Dougherty R.C. Effects of electric and magnetic fields on prochiral chemical reactions: macroscopic electric and magnetic fields can cause asymmetric synthesis. J Am Chem Soc 1978, 100:6247-6248.
11. Barron L.D. Can a magnetic field induce absolute asymmetric synthesis?. Science 1994, 266:1491-1492.
12. Rikken G.L.J.A., Raupach E. Pure and cascaded magnetochiral anisotropy in optical absorption. Phys Rev E: Stat Phys Plasmas Fluids Relat Interdiscip Top 1998, 58:5081-5084.
13. Rikken G.L.J.A., Raupach E. Enantioselective magnetochiral photochemistry. Nature 2000, 405:932-935.
14. Meierhenrich U.J., Nahon L., Alcaraz C., Bredehoft J.H., Hoffmann S.V., Barbier B., et al. Asymmetric vacuum UV photolysis of the amino acid leucine in the solid state. Angew Chem Int Ed 2005, 44:5630-5634.
15. Meierhenrich U., Filippi J.J., Meinert C., Hoffmann S.V., Bredehoft J.H., Nahon L. Photolysis of rac-leucine with circularly polarized synchrotron radiation. Chem Biodiv 2010, 7:1651-1659.
16. Meierhenrich U.J., Filippi J.-J., Meinert C., Bredehöft J.H., Takahashi J.-i., Nahon L., et al. Circular dichroism of amino acids in the vacuum-ultraviolet region. Angew Chem Int Ed 2010, 49:7799-7802.
17. Adrian-Scotto M., Antonczak S., Bredehöft J.H., Hoffmann S.V., Meierhenrich U.J. Chiroptical properties of amino acids: a density functional theory study. Symmetry 2010, 2:935-949.
18. Glavin D.P., Dworkin J.P. Enrichment of the amino acid L-isovaline by aqueous alteration on CI and CM meteorite parent bodies. Proc Natl Acad Sci 2009, 106:5487-5492.
19. Nahon L., Alcaraz C. SU5: a calibrated variable-polarization synchrotron radiation beam line in the vacuum-ultraviolet range. Appl Opt 2004, 43:1024-1037.
20. De Marcellus P., Meinert C., Nuevo M., Filippi J.-J., Danger G., Deboffle D., et al. Non-racemic amino acid production by ultraviolet irradiation of achiral interstellar ice analogs with circularly polarized light. ApJ 2011, 727. L27/1-L/6.
21. Greenberg J.M. What are comets made of? A model based on interstellar dust. Comets 1982, 131-163.
22. Greenberg J.M. Chemical evolution in space. Orig Life 1984, 24:25-36.
23. Greenberg J.M. Chirality in interstellar dust and in comets: life from dead stars. AIP Conf Proc 1996, 379:185-210.
24. Oro J. Comets and formation of biochemical compounds on primitive Earth. Nature 1961, 190:389-390.
25. Chyba C.F., Thomas P.J., Brookshaw L., Sagan C. Cometary delivery of organic molecules to the early Earth. Science 1990, 249:366-373.
26. Goesmann F., Rosenbauer H., Roll R., Szopa C., Raulin F., Sternberg R., et al. COSAC, the cometary sampling and composition experiment on Philae. Space Sci Rev 2007, 128:257-280.
27. Thiemann W.H.P., Meierhenrich U. ESA mission ROSETTA will probe for chirality of cometary amino acids. Orig Life Evol Biosph 2001, 31:199-210.
28. Irvine W.M. The molecular composition of dense interstellar clouds. NATO ASI Ser C 1991, 323:89-121.
29. Herbst E., van Dishoeck E.F. Complex organic interstellar molecules. Annu Rev Astron Astrophys 2009, 47:427-480.
30. http://astrochymist.org/astrochymist_ism.html.
31. Bell M.B., Feldman P.A., Watson J.K.G., McCarthy M.C., Travers M.J., Gottlieb C.A., et al. Observations of long CnH molecules in the dust cloud TMC-1. Astrophys J 1999, 518:740-747.
32. Ehrenfreund P., Charnley S.B. Organic molecules in the interstellar medium, comets, and meteorites: a voyage from dark clouds to the early Earth. Annu Rev Astron Astrophys 2000, 38:427-483.
33. Garrod R.T., Weaver S.L.W., Herbst E. Complex chemistry in star-forming regions: an expanded gas-grain warm-up chemical model. Astrophys J 2008, 682:283-302.
34. Greenberg J.M. The role of grains in molecular chemical evolution. Astrophys Space Sci 1986, 128:17-31.
35. Ehrenfreund P., Fraser H. Ice chemistry in space, solid state astrochemistry 2003, Kluwer Academic Publishers, Dordrecht.
36. Gibb E.L., Whittet D.C.B., Boogert A.C.A., Tielens A.G.G.M. Interstellar ice. The Infrared space observatory legacy. Astrophys J Suppl Ser 2004, 151:35-73.
37. 2 ice mixtures and their astrophysical implications. Astron Astrophys 1999, 350:240-253.
38. Dartois E. Space Sci Rev 2005, 119:293-310.
39. Tielens A.G.G.M., Hagen W. Model calculations of the molecular composition of interstellar grain mantles. Astron Astrophys 1982, 114:245-260.
40. D'Hendecourt L.B., Allamandola L.J., Greenberg J.M. Time dependent chemistry in dense molecular clouds. I. Grain surface reactions, gas/grain interactions and infrared spectroscopy. Astron Astrophys 1985, 152:130-150.
41. Ehrenfreund P., Boogert A.C.A., Gerakines P.A., Tielens A.G.G.M., Van D.E.F. Infrared spectroscopy of interstellar apolar ice analogs. Astron Astrophys 1997, 328:649-669.
42. Smoluchowski R. Amorphous ice on Saturnian rings and on icy satellites: its formation, stability, and observability. Science 1978, 4358:809-811.
43. Smoluchowski R. Solar system ice: amorphous or crystalline?. Science 1983, 222:161-163.
44. Pontoppidan K.M., Fraser H.J., Dartois E., Thi W.F., Van D.E.F., Boogert A.C.A., et al. A 3-5 μm VLT spectroscopic survey of embedded young low mass stars. Part 1. Structure of the CO ice. Astron Astrophys 2003, 408:981-1007.
45. Accolla M., Congiu E., Dulieu F., Manico G., Chaabouni H., Matar E., et al. Changes in the morphology of interstellar ice analogues after hydrogen atom exposure. Phys Chem Chem Phys 2011, 13:8037-8045.
46. Allamandola L.J., Bernstein M.P., Sandford S.A., Walker R.L. Evolution of interstellar ices. Space Sci Rev 1999, 90:219-232.
47. Chiar J.E. The nature and evolution of interstellar ices. Orig Life Evol Biosph 1997, 27:79-100.
48. Duley W.W. Chemical evolution of carbonaceous material in interstellar clouds. Astrophys J 2000, 528:841-848.
49. Moore M.H., Donn B., Khanna R., A'Hearn M.F. Studies of proton-irradiated cometary-type ice mixtures. Icarus 1983, 54:388-405.
50. Millar T.J. Molecules in high-mass star-forming regions. Theory and observation. Astron Soc Pac Conf Ser 2001, 235:45-58.
51. Kuan Y.-J., Charnley S.B., Huang H.-C., Tseng W.-L., Kisiel Z. Interstellar glycine. Astrophys J 2003, 593:848-867.
52. Snyder L.E., Lovas F.J., Hollis J.M., Friedel D.N., Jewell P.R., Remijan A., et al. A rigorous attempt to verify interstellar glycine. Astrophys J 2005, 619:914-930.
53. Greenberg J.M., Yencha A.J., Corbett J.W., Frisch H.L. Ultraviolet effects on the chemical composition and optical properties of interstellar grains. Mem Soc Roy Sci 1972, 3:425-436.
54. Bernstein M.P., Allamandola L.J., Sandford S.A. Complex organics in laboratory simulations of interstellar/cometary ices. Adv Space Res 1997, 19:991-998.
55. Cottin H., Szopa C., Moore M.H. Production of hexamethylenetetramine in photolyzed and irradiated interstellar cometary ice analogs. ApJ 2001, 561. L139-L42.
56. Briggs R., Ertem G., Ferris J.P., Greenberg J.M., McCain P.J., Mendoza-Gomez C.X., et al. Comet Halley as an aggregate of interstellar dust and further evidence for the photochemical formation of organics in the interstellar medium. Orig Life Evol Biosph 1992, 22:287-307.
57. Bredehoft J.H., Meierhenrich U.J. Amino acid structures from UV irradiation of simulated interstellar ices 2008, Transworld Research Network, Kerala, India.
58. Cronin J.R., Pizzarello S. Amino acids in meteorites. Adv Space Res 1983, 3:5-18.
59. Takano Y., Ohashi A., Kaneko T., Kobayashi K. Abiotic synthesis of high-molecular-weight organics from an inorganic gas mixture of carbon monoxide, ammonia, and water by 3 MeV proton irradiation. Appl Phys Lett 2004, 84:1410-1412.
60. Takano Y., Kaneko T., Kobayashi K., Hiroishi D., Ikeda H., Marumo K. Experimental verification of photostability for free- and bound-amino acids exposed to gamma-rays and UV irradiation. Earth Planets Space 2004, 56:669-674.
61. Danger G., Bossa J.B., De Marcellus P., Borget F., Duvernay F., Theulé P., et al. Experimental investigation of nitrile formation from VUV photochemistry of interstellar ices analogs: acetonitrile and amino acetonitrile. Astron Astrophys 2011, 525.
62. DHendecourt L.B., Allamandola L.J., Baas F., Greenberg J.M. Inter-stellar grain explosions - molecule cycling between gas and dust. Astron Astrophys 1982, 109. L12-L4.
63. Woon D.E. Pathways to glycine and other amino acids in ultraviolet-irradiated astrophysical ices determined via quantum chemical modeling. ApJ 2002, 571. L177-L80.
64. Mendoza C., Ruette F., Martorell G., Rodriguez L.S. Quantum-chemical modeling of interstellar grain prebiotic chemistry: catalytic synthesis of glycine and alanine on the surface of a polycyclic aromatic hydrocarbon flake. ApJ 2004, 601. L59-L62.
65. Elsila J.E., Dworkin J.P., Bernstein M.P., Martin M.P., Sandford S.A. Mechanisms of amino acid formation in interstellar ice analogs. Astrophys J 2007, 660:911-918.
66. Kobayashi K., Takano Y., Masuda H., Tonishi H., Kaneko T., Hashimoto H., et al. Possible cometary organic compounds as sources of planetary biospheres. Adv Space Res 2004, 33:1277-1281.
67. Takahashi J.-i., Masuda H., Kaneko T., Kobayashi K., Saito T., Hosokawa T. Photochemical abiotic synthesis of amino-acid precursors from simulated planetary atmospheres by vacuum ultraviolet light. J Appl Phys 2005, 98(024907):1-6.
68. Nuevo M., Auger G., Blanot D., d'Hendecourt L. A detailed study of the amino acids produced from the vacuum UV irradiation of interstellar ice analogs. Orig Life Evol Biosph 2008, 38:37-56.
69. Takano Y., Tsuboi T., Kaneko T., Kobayashi K., Marumo K. Pyrolysis of high-molecular-weight complex organics synthesized from a simulated interstellar gas mixture irradiated with 3 MeV proton beam. Bull Chem Society Japan 2004, 77:779-783.
70. Takahashi J.-i., Hosokawa T., Masuda H., Kaneko T., Kobayashi K., Saito T., et al. Abiotic synthesis of amino acids by x-ray irradiation of simple inorganic gases. Appl Phys Lett 1999, 74:877-879.
71. Takano Y., Masuda H., Kaneko T., Kobayashi K. Formation of amino acids from possible interstellar media by gamma-rays and UV irradiation. Chem Lett 2002, 986-987.
72. Takano Y., Marumo K., Yabashi S., Kaneko T., Kobayashi K. Pyrolysis of complex organics following high-energy proton irradiation of a simple inorganic gas mixture. Appl Phys Lett 2004, 85:1633-1635.
73. Nuevo M., Bredehoft J.H., Meierhenrich U., d'Hendecourt L., Thiemann W. Urea, glycerol and glycolic acid in an organic residue produced by UV irradiation of interstellar/pre-cometary ice analogues. Astrobiology 2010, 10:245-256.
74. Meierhenrich U.J., Muñoz Caro G.M., Schutte W.A., Thiemann W.H.P., Barbier B., Brack A. Cover picture: precursors of biological cofactors from ultraviolet irradiation of circumstellar/interstellar ice analogues. Chem Eur J 2005, 11:4855.
75. De Bertrand PM, Nuevo M, Westall F, D'Hendecourt LLS. Prebiotic significance of extraterrestrial ice photochemistry: detection of hydantoin in organic residues. Astrobiology 2011 [in press].
76. Thrower J.D., Collings M.P., Rutten F.J.M., McCoustra M.R.S. Laboratory investigations of the interaction between benzene and bare silicate grain surfaces. Mon Not R Astron Soc 2009, 394:1510-1518.
77. Green S.D., Bolina A.S., Chen R., Collings M.P., Brown W.A., McCoustra M.R.S. Applying laboratory thermal desorption data in an interstellar context: sublimation of methanol thin films. Mon Not R Astron Soc 2009, 398:357-367.
78. Munoz Caro G.M., Meierhenrich U.J., Schutte W.A., Thiemann W.H.P., Greenberg J.M. UV-photoprocessing of interstellar ice analogs: detection of hexamethylenetetramine-based species. Astron Astrophys 2004, 413:209-216.
79. Viti S., Collings M.P., Dever J.W., McCoustra M.R.S., Williams D.A. Evaporation of ices near massive stars: models based on laboratory temperature programmed desorption data. Mon Not R Astron Soc 2004, 354:1141-1145.
80. Grady M.M., Hey M.H. Catalogue of meteorites 2000, Cambridge University Press, New York. 5th ed.
81. Van Schmus W.R., Hayes J.M. Chemical petrographic correlations among carbonaceous chondrites. Geochim Cosmochim Acta 1974, 38:47-48. IN1, 9-64.
82. 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 1980, 44:1543-1577.
83. Chyba C., Sagan C. Endogenous production, exogenous delivery and impact-shock synthesis of organic molecules: an inventory for the origins of life. Nature 1992, 355:125-132.
84. Hayatsu R., Matsuoka S., Scott R.G., Studier M.H., Anders E. Origin of organic matter in the early Solar system-VII. The organic polymer in carbonaceous chondrites. Geochim Cosmochim Acta 1977, 41:1325-1339.
85. Robert F., Epstein S. The concentration and isotopic composition of hydrogen, carbon and nitrogen in carbonaceous meteorites. Geochim Cosmochim Acta 1982, 46:81-95.
86. Clayton R.N., Mayeda T.K. The oxygen isotope record in Murchison and other carbonaceous chondrites. Earth Planet Sci Lett 1984, 67:151-161.
87. Jones R.H., Leshin L.A., Guan Y., Sharp Z.D., Durakiewicz T., Schilk A.J. Oxygen isotope heterogeneity in chondrules from the Mokoia CV3 carbonaceous chondrite. Geochim Cosmochim Acta 2004, 68:3423-3438.
88. Cronin J.R., Chang S. Organic matter in meteorites: molecular and isotopic analyses of the Murchison meteorite 1993, Kluwer, Dordrecht. Chemistry of life's origins ed.
89. Sephton M.A. Organic compounds in carbonaceous meteorites. Nat Prod Rep 2002, 19:292-311.
90. Stoks P.G., Schwartz A.W. Uracil in carbonaceous meteorites. Nature 1979, 282:709-710.
91. Stoks P.G., Schwartz A.W. Basic nitrogen-heterocyclic compounds in the Murchison meteorite. Geochim Cosmochim Acta 1982, 46:309-315.
92. Martins Z., Botta O., Fogel M.L., Sephton M.A., Glavin D.P., Watson J.S., et al. Extraterrestrial nucleobases in the Murchison meteorite. Earth Planet Sci Lett 2008, 270:130-136.
93. Martins Z., Botta O., Fogel M.L., Sephton M.A., Glavin D.P., Watson J.S., et al. Extraterrestrial nucleobases in the Murchison meteorite. Orig Life Evol Biosph 2009, 39:214.
94. Claus G., Nagy B. A microbiological examination of some carbonaceous chondrites. Nature 1961, 192:594-596.
95. Degens E.T., Bajor M. Amino acids and sugars in the Bruderheim and Murray meteorite. Naturwissenschaften 1962, 49:605-606.
96. Oro J., Skewes H.B. Free amino-acids on human fingers: the question of contamination in microanalysis. Nature 1965, 207:1042-1045.
97. Hamilton P.B. Amino-acids on hands. Nature 1965, 205:284-285.
98. Kvenvolden K.A., Lawless J., Pering K., Peterson E., Flores J., Ponnamperuma C., et al. Evidence for extraterrestrial amino-acids and hydrocarbons in the Murchison meteorite. Nature 1970, 228:923-926.
99. Oro J., Gibert J., Lichtenstein H., Wikstrom S., Flory D.A. Amino-acids, aliphatic and aromatic hydrocarbons in the Murchison meteorite. Nature 1971, 230:105-106.
100. Kvenvolden K.A., Lawless J.G., Ponnamperuma C. Nonprotein amino acids in the Murchison meteorite. Proc Natl Acad Sci USA 1971, 68:486-490.
101. Cronin J.R., Pizzarello S. Amino acids of the Murchison meteorite. III. Seven carbon acyclic primary alpha-amino alkanoic acids. Geochim Cosmochim Acta 1986, 50:2419-2427.
102. Pizzarello S., Huang Y.S., Fuller M. The carbon isotopic distribution of Murchison amino acids. Geochim Cosmochim Acta 2004, 68:4963-4969.
103. Cronin J.R. Acid-labile amino acid precursors in the Murchison meteorite. I: chromatographic fractionation. Orig Life Evol Biosph 1976, 7:337-342.
104. Schmitt-Kopplin P., Gabelica Z., Gougeon Rg.D., Fekete A., Kanawati B., Harir M., et al. High molecular diversity of extraterrestrial organic matter in Murchison meteorite revealed 40 years after its fall. Proc Natl Acad Sci 2010, 107:2763-2768.
105. Nielsen P.E. Peptide nucleic-acid (PNA) - a model structure for the primordial genetic material. Orig Life Evol Biosph 1993, 23:323-327.
106. Nielsen P.E., Egholm M., Berg R.H., Buchardt O. Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide. Science 1991, 254:1497-1500.
107. Yuen G., Blair N., Desmarais D.J., Chang S. Carbon isotope composition of low-molecular weight hydrocarbons and monocarboxylic acids from Murchison meteorite. Nature 1984, 307:252-254.
108. Epstein S., Krishnamurthy R.V., Cronin J.R., Pizzarello S., Yuen G.U. Unusual stable isotope ratios in amino-acid and carboxylic-acid extracts from the Murchison meteorite. Nature 1987, 326:477-479.
109. Engel M.H., Macko S.A., Silfer J.A. Carbon isotope composition of individual amino-acids in the Murchison meteorite. Nature 1990, 348:47-49.
110. Pizzarello S., Krishnamurthy R.V., Epstein S., Cronin J.R. Isotopic analyses of amino-acids from the Murchison meteorite. Geochim Cosmochim Acta 1991, 55:905-910.
111. Pizzarello S., Feng X., Epstein S., Cronin J.R. Isotopic analyses of nitrogenous compounds from the Murchison meteorite - ammonia, amines, amino-acids, and polar hydrocarbons. Geochim Cosmochim Acta 1994, 58:5579-5587.
112. Engel M.H., Macko S.A. Isotopic evidence for extraterrestrial non-racemic amino acids in the Murchison meteorite. Nature 1997, 389:265-268.
113. Pizzarello S., Huang Y.S. Carbon isotopic analyses of individual Murchison amino acids. Geochim Cosmochim Acta 2003, 67. A380-A.
114. Pizzarello S., Huang Y.S. The deuterium enrichment of individual amino acids in carbonaceous meteorites: a case for the presolar distribution of biomolecule precursors. Geochim Cosmochim Acta 2005, 69:599-605.
115. Brückner H., Becker D., Gams W., Degenkolb T. Aib and iva in the biosphere: neither rare nor necessarily extraterrestrial. Chem Biodiv 2009, 6:38-56.
116. Cronin J.R., Moore C.B. Amino acid analyses of Murchison, Murray, and Allende carbonaceous chondrites. Science 1971, 172:1327-1328.
117. Ehrenfreund P., Glavin D.P., Botta O., Cooper G., Bada J.L. Extraterrestrial amino acids in Orgueil and Ivuna: tracing the parent body of Cl type carbonaceous chondrites. Proc Natl Acad Sci USA 2001, 98:2138-2141.
118. Shimoyama A., Ponnamperuma C., Yanai K. Amino acids in the Yamato carbonaceous chondrite from Antarctica. Nature 1979, 282:394-396.
119. Shimoyama A., Harada K., Yanai K. Amino acids from the YAMATO-791198 carbonaceous chondrite from Antarctica. Chem Lett 1985, 14:1183-1186.
120. Martins Z., Alexander C.M.O.D., Orzechowska G.E., Fogel M.L., Ehrenfreund P. Indigenous amino acids in primitive CR meteorites. Meteorit Planet Sci 2007, 42:2125-2136.
121. Pizzarello S., Huang Y., Alexandre M.R. Molecular asymmetry in extraterrestrial chemistry: insights from a pristine meteorite. Proc Natl Acad Sci 2008, 105:3700-3704.
122. Cody G.D., Alexander C.M.O.D. NMR studies of chemical structural variation of insoluble organic matter from different carbonaceous chondrite groups. Geochim Cosmochim Acta 2005, 69:1085-1097.
123. Botta O., Martins Z., Ehrenfreund P. Amino acids in Antarctic CM1 meteorites and their relationship to other carbonaceous chondrites. Meteorit Planet Sci 2007, 42:81-92.
124. Glavin D.P., Callahan M.P., Dworkin J.P., Elsila J.E. The effects of parent body processes on amino acids in carbonaceous chondrites. Meteorit Planet Sci 2011, 45:1948-1972.
125. Glavin D.P., Dworkin J.P., Aubrey A., Botta O., Doty J.H., Martins Z., et al. Amino acid analyses of Antarctic CM2 meteorites using liquid chromatography-time of flight-mass spectrometry. Meteorit Planet Sci 2006, 41:889-902.
126. 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 1995, 59:1003-1015.
127. Cronin J.R. Acid-labile amino acid precursors in the Murchison meteorite. II: a search for peptides and amino acyl amides. Orig Life Evol Biosph 1976, 7:343-348.
128. Peltzer E.T., Bada J.L. Alpha-hydroxycarboxylic acids in the Murchison meteorite. Nature 1978, 272:443-444.
129. Cronin J.R., Pizzarello S., Epstein S., Krishnamurthy R.V. Molecular and isotopic analyses of the hydroxy acids, dicarboxylic acids, and hydroxydicarboxylic acids of the Murchison meteorite. Geochim Cosmochim Acta 1993, 57:4745-4752.
130. 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 dicarboxylic acids. Adv Space Res 1984, 4:69-74.
131. Cronin J.R., Cooper G.W., Pizzarello S. Characteristics and formation of amino acids and hydroxy acids of the Murchison meteorite. Adv Space Res 1995, 15:91-97.
132. Matthews C., Nelson J., Varma P., Minard R. Deuterolysis of amino acid precursors: evidence for hydrogen cyanide polymers as protein ancestors. Science 1977, 198:622-625.
133. Blagojevic V., Petrie S., Bohme D.K. Gas-phase syntheses for interstellar carboxylic and amino acids. Mon Not R Astron Soc 2003, 339. L7-L11.
134. Largo A., Redondo P., Barrientos C. Theoretical study of possible ion-molecule reactions leading to precursors of glycine in the interstellar medium. Int J Quantum Chem 2004, 98:355-360.
135. Chaban G.M., Pizzarello S. Ab initio calculations of 6- and 7-carbon meteoritic amino acids and their diastereomers. Meteorit Planet Sci 2010, 45:1053-1060.
136. Cronin J.R., Pizzarello S. Enantiomeric excesses in meteoritic amino acids. Science 1997, 275:951-955.
137. Pizzarello S., Cronin J.R. Non-racemic amino acids in the Murray and Murchison meteorites. Geochim Cosmochim Acta 2000, 64:329-338.
138. Brückner H., Maisch J., Reinecke C., Kimonyo A. Use of α-aminoisobutyric acid and isovaline as marker amino acids for the detection of fungal polypeptide antibiotics. Screening of Hypocrea. Amino Acids 1991, 1:251-257.
139. Yamagata Y. A hypothesis for the asymmetric appearance of biomolecules on Earth. J Theor Biol 1966, 11:495-498.
140. Goldhaber M., Grodzins L., Sunyar A.W. Evidence for circular polarization of bremsstrahlung produced by β-rays. Phys Rev 1957, 106:826-828.
141. Vester F., Ulbricht T.L.V., Krauch H. Optical activity and parity violation in β-decay. Naturwissenschaften 1959, 46:68.
142. Bonner W.A. Experiments on the origin of molecular chirality by parity nonconservation during β-decay. J Mol Evol 1974, 4:23-39.
143. Pollock G.E., Cheng C.N., Cronin S.E., Kvenvolden K.A. Stereoisomers of isovaline in the Murchison meteorite. Geochim Cosmochim Acta 1975, 39:1571-1573.
144. Bonner W.A., Blair N.E., Lemmon R.M., Flores J.J., Pollock G.E. The radioracemization of isovaline. Cosmochemical implications. Geochim Cosmochim Acta 1979, 43:1841-1846.
145. Bada J.L., Miller S.L. Racemization and the origin of optically-active organic-compounds in living organisms. BioSystems 1987, 20:21-26.
146. Cohen B.A., Chyba C.F. Racemization of meteoritic amino acids. Icarus 2000, 145:272-281.
147. Cronin J.R., Pizzarello S. Amino acid enantiomer excesses in meteorites: origin and significance. Life sciences: exobiology 1999, 293-299. Pergamon Press Ltd, Oxford. F. Raulin, K. Kobayashi, A. Brack (Eds.).
148. Pizzarello S., Weber A.L. Prebiotic amino acids as asymmetric catalysts. Science 2004, 303:1151.
149. 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 USA 2010, 107:5723-5725.
150. Weber A.L., Pizzarello S. The peptide-catalyzed stereospecific synthesis of tetroses: a possible model for prebiotic molecular evolution. Proc Natl Acad Sci USA 2006, 103:12713-12717.
151. Pizzarello S., Weber A.L. Stereoselective syntheses of pentose sugars under realistic prebiotic conditions. Orig Life Evol Biosph 2010, 40:3-10.
152. Pizzarello S., Zolensky M., Turk K.A. Nonracemic isovaline in the Murchison meteorite: chiral distribution and mineral association. Geochim Cosmochim Acta 2003, 67:1589-1595.
153. Pasek M., Lauretta D. Extraterrestrial flux of potentially prebiotic C, N, and P to the early Earth. Orig Life Evol Biosph 2008, 38:5-21.
154. Engrand C., Maurette M. Carbonaceous micrometeorites from Antarctica. Meteorit Planet Sci 1998, 33:565-580.
155. Matrajt G., Pizzarello S., Taylor S., Brownlee D. Concentration and variability of the AIB amino acid in polar micrometeorites: implications for the exogenous delivery of amino acids to the primitive Earth. Meteorit Planet Sci 2004, 39:1849-1858.
156. Botta O., Glavin D.P., Dworkin J.P., Matrajt G., Harvey R.P. Detection of AIB in Antarctic ice samples: implications for exogenous delivery of prebiotic organic compounds. Orig Life Evol Biosph 2009, 39:225-226.
157. Schopf J.W. Microfossils of the early archean apex chert: new evidence of the antiquity of life. Science 1993, 260:640-646.
158. Holland H.D. Evidence for life on Earth more than 3850 million years ago. Science 1997, 275:38-39.
159. Feng D.-F., Cho G., Doolittle R.F. Determining divergence times with a protein clock: update and reevaluation. Proc Natl Acad Sci 1997, 94:13028-13033.
160. Greenberg J.M. The structure and evolution of interstellar grains. Sci Am 1984, 250:124-154.
161. Anders E. Pre-biotic organic matter from comets and asteroids. Nature 1989, 342:255-257.
162. Gorti U., Dullemond C.P., Hollenbach D. Time evolution of viscous circumstellar disks due to photoevaporation by far-ultraviolet, extreme-ultraviolet, and X-ray radiation from the central star. Astrophys J 2009, 705:1237-1251.
163. Peeters Z., Botta O., Charnley S.B., Kisiel Z., Kuan Y.J., Ehrenfreund P. Formation and photostability of N-heterocycles in space. Astron Astrophys 2005, 433:583-590.
164. Ehrenfreund P., Bernstein M.P., Dworkin J.P., Sandford S.A., Allamandola L.J. The photostability of amino acids in space. Astrophys J 2001, 550. L95-L9.
165. Peeters Z., Botta O., Charnley S.B., Ruiterkamp R., Ehrenfreund P. The astrobiology of nucleobases. ApJ 2003, 593. L129-L32.
166. Pilling S., Andrade D.P.P., do Nascimento E.M., Marinho R.R.T., Boechat-Roberty H.M., de Coutinho L.H., et al. Photostability of gas- and solid-phase biomolecules within dense molecular clouds due to soft X-rays. Mon Not R Astron Soc 2011, 411:2214-2222.
167. Elsila J.E., Glavin D.P., Dworkin J.P. Cometary glycine detected in samples returned by Stardust. Meteorit Planet Sci 2009, 44:1323-1330.
168. Pierazzo E., Chyba C.F. Amino acid survival in large cometary impacts. Meteorit Planet Sci 1999, 34:909-918.
169. Matrajt G., Brownlee D., Sadilek M., Kruse L. Survival of organic phases in porous IDPs during atmospheric entry: a pulse-heating study. Meteorit Planet Sci 2006, 41:903-911.
170. Botta O., Glavin D.P., Kminek G., Bada J.L. Relative amino acid concentrations as a signature for parent body processes of carbonaceous chondrites. Orig Life Evol Biosph 2002, 32:143-163.
171. Sephton M.A., Verchovsky A.B., Bland P.A., Gilmour I., Grady M.M., Wright I.P. Investigating the variations in carbon and nitrogen isotopes in carbonaceous chondrites. Geochim Cosmochim Acta 2003, 67:2093-2108.
172. Bonner W.A. The origin and amplification of biomolecular chirality. Orig Life Evol Biosph 1991, 21:59-111.
173. Curie P. Sur la symétrie des phénomènes physiques: symétrie d'un champ électrique et d'un champ magnétique. J Phys 1894, 3:393-415.
174. 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.
175. Rubenstein E., Bonner W.A., Noyes H.P., Brown G.S. Supernovae life. Nature 1983, 306:118.
176. Bonner W.A., Rubenstein E. Supernovae, neutron stars and biomolecular chirality. BioSystems 1987, 20:99-111.
177. Bailey J., Chrysostomou A., Hough J.H., Gledhill T.M., McCall A., Clark S., et al. Circular polarization in star-formation regions: implications for biomolecular homochirality. Science 1998, 281:672-674.
178. Bailey J. Astronomical sources of circularly polarized light and the origin of homochirality. Orig Life Evol Biosph 2001, 31:167-183.
179. Fukue T.M.T., Kandori R., Kusukabe N., Hough J.H., Bailey J., Whittet D.C.B., et al. Extended high circular polarization in the Orion massive star forming region: implications for the origin of homochirality in the Solar system. Orig Life Evol Biosph 2010, 40:335-346.
180. Menard F., Chrysostomou A., Gledhill T., Hough J.H., Bailey J. High circular polarization in the star forming region NGC 6334: implications for biomoleclar homochirality. Astron Soc Pac Conf Ser 2000, 213:355-358.
181. Lucas P.W., Hough J.H., Bailey J., Chrysostomou A., Gledhill T.M., McCall A. UV circular polarisation in star formation regions: the origin of homochirality?. Orig Life Evol Biosph 2005, 35:29-60.
182. 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.
183. Nishino H., Kosaka A., Hembury G.A., Matsushima K., Inoue Y. The pH dependence of the anisotropy factors of essential amino acids. J Chem Soc Perkin Trans 2002, 2:582-590.
184. Nishino H., Kosaka A., Hembury G.A., Shitomi H., Onuki H., Inoue Y. Mechanism of pH-dependent photolysis of aliphatic amino acids and enantiomeric enrichment of racemic leucine by circularly polarized light. Org Lett 2001, 3:921-924.
185. Naito Y, Nishino H, Inoue Y. The absolute asymmetric synthesis by two-photon excitation using femtosecond circularly polarized pulse. In: Proceedings of the photochirogenesis symposium. Osaka, Japan, September 2001.
186. Bonner W.A., Bean B.D. Asymmetric photolysis with elliptically polarized light. Orig Life Evol Biosph 2000, 30:513-517.
187. Norden B. Was photoresolution of amino acids the origin of optical activity in life?. Nature 1977, 266:567-568.
188. Cerf C., Jorissen A. Is amino-acid homochirality due to asymmetric photolysis in space?. Space Sci Rev 2000, 92:603-612.
189. http://www.synchrotron-soleil.fr/portal/page/portal/Recherche/LignesLumiere/DESIRS.
190. Takahashi J., Shinojima H., Seyama M., Ueno Y., Kaneko T., Kobayashi K., et al. Chirality emergence in thin solid films of amino acids by polarized light from synchrotron radiation and free electron laser. Int J Mol Sci 2009, 10:3044-3064.
191. Mason S.F. Extraterrestrial handedness. Nature 1997, 389:804.
192. Buchardt O. Photochemistry with circularly polarized light. Angew Chem Int Ed 1974, 13:179-185.
193. Kagan H., Moradpour A., Nicoud J.F., Balavoine G., Martin R.H., Cosyn J.P. Photochemistry with circularly polarized light. II. Asymmetric synthesis of octa- and nonahelicene. Tetrahedron Lett 1971, 2479-2482.
194. Rau H. Asymmetric photochemistry in solution. Chem Rev 1983, 83:535-547.
195. Barron L.D. Fundamental symmetry aspects of chirality. BioSystems 1987, 20:7-14.
196. Barron L.D. True and false chirality and parity violation. Chem Phys Lett 1986, 123:423-427.
197. Takano Y., Takahashi J., Kaneko T., Marumo K., Kobayashi K. Asymmetric synthesis of amino acid precursors in interstellar complex organics by circularly polarized light. Earth Planet Sci Lett 2007, 254:106-114.
198. Nuevo M., Meierhenrich U.J., Caro G.M.M., Dartois E., d'Hendecourt L., Deboffle D., et al. The effects of circularly polarized light on amino acid enantiomers produced by the UV irradiation of interstellar ice analogs. Astron Astrophys 2006, 457:741-751.
199. Nuevo M., Meierhenrich U.J., d'Hendecourt L., Caro G.M.M., Dartois E., Deboffle D., et al. Enantiomeric separation of complex organic molecules produced from irradiation of interstellar/circumstellar ice analogs. Adv Space Res 2007, 39:400-404.
200. Blackmond D.G. Asymmetric autocatalysis and its implications for the origin of homochirality. Proc Natl Acad Sci 2004, 101:5732-5736.
201. Plasson R., Bersini H., Commeyras A. Recycling Frank spontaneous emergence of homochirality in noncatalytic systems. Proc Natl Acad Sci USA 2004, 101:16733-16738.
202. Klussmann M., Iwamura H., Mathew S.P., Wells D.H., Pandya U., Armstrong A., et al. Thermodynamic control of asymmetric amplification in amino acid catalysis. Nature 2006, 441:621-623.
203. Soai K., Shibata T., Morioka H., Choji K. Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule. Nature 1995, 378:767-768.
204. Millar T.J., Bennett A., Herbst E. Deuterium fractionation in dense interstellar clouds. Astrophys J 1989, 340:906-920.
205. Tielens A.G.G.M. Surface chemistry of deuterated molecules. Astron Astrophys 1983, 119:177-184.
206. Kissel J., Krueger F.R. The organic component in dust from comet Halley as measured by the PUMA mass spectrometer on board Vega 1. Nature 1987, 326:755-760.
207. Kissel J., Krueger F.R., Silen J., Clark B.C. The cometary and interstellar dust analyzer at comet 81P/Wild 2. Science 2004, 304:1774-1776.
208. Huebner W.F., Boice D.C. Comets as a possible source of prebiotic molecules. Orig Life Evol Biosph 1992, 21:299-315.
209. Brownlee D., Tsou P., Aleon J., et al. Research article - Comet 81P/Wild 2 under a microscope. Science 2006, 314:1711-1716.
210. Jordan I.K., Kondrashov F.A., Adzhubei I.A., Wolf Y.I., Koonin E.V., Kondrashov A.S., et al. A universal trend of amino acid gain and loss in protein evolution. Nature 2005, 433:633-638.
211. Trifonov E.N. Cracking the chromatin code: precise rule of nucleosome positioning. Phys Life Rev 2011, 8:39-50.
212. Meierhenrich U.J., Filippi J.-J., Meinert C., Vierling P., Dworkin J.P. On the origin of primitive cells: from nutrient intake to elongation of encapsulated nucleotides. Angew Chem Int Ed 2010, 49:3738-3750.