Miller-Urey and beyond: What have we learned about prebiotic organic synthesis reactions in the past 60 years?

Annual Review of Earth and Planetary Sciences

Volumn 41, Issue , 2013, Pages 207-229

  McCollom, Thomas M ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

Organic geochemistry; Origin of life; Prebiotic synthesis

Indexed keywords

BASIC BUILDING BLOCK; EXPERIMENTAL STUDIES; LABORATORY SIMULATION; ORGANIC CHEMISTRY; ORGANIC GEOCHEMISTRY; ORIGIN OF LIFE; PREBIOTIC CONDITIONS; PREBIOTICS;

AMINO ACIDS;

AMINO ACID; EARLY EARTH; LABORATORY METHOD; LIPID; ORGANIC GEOCHEMISTRY; ORIGIN OF LIFE; SUGAR;

EID: 84878679364     PISSN: 00846597     EISSN: None     Source Type: Book Series    
DOI: 10.1146/annurev-earth-040610-133457     Document Type: Article

References (123)

1. Abelson PH. 1966. Chemical events on the primitive Earth. Proc. Natl. Acad. Sci. USA 55:1365-72
2. AllenWV, Ponnamperuma C. 1967. A possible prebiotic synthesis of monocarboxylic acids. Curr. Mod. Biol. 1:24-28
3. Anders E, Hayatsu R, Studier MH. 1973. Organic compounds in meteorites. Science 182:781-90
4. Aubrey AD, Cleaves HJ, Bada JL. 2009. The role of submarine hydrothermal systems in the synthesis of amino acids. Orig. Life Evol. Biosph. 39:91-108
5. Bada JL, Lazcano A. 2000. Stanley Miller's 79th birthday. Orig. Life Evol. Biosph. 30:107-12
6. Bada JL, Miller SL. 1970. The kinetics andmechanism of the reversible nonenzymatic deamination of aspartic acid. J. Am. Chem. Soc. 92:2774-82
7. Bada JL, Miller SL, Zhao M. 1995. The stability of amino acids at submarine hydrothermal vent temperatures. Orig. Life Evol. Biosph. 30:107-12
8. Baross JA, Hoffman SE. 1985. Submarine hydrothermal vents and associated gradient environments as sites for the origin and evolution of life. Orig. Life Evol. Biosph. 15:327-45
9. Bean HD, Sheng Y, Collins JP, Anet FAL, Leszczynski J, Hud NV. 2007. Formation of a β-pyrimidine nucleoside by a free pyrimidine base and ribose in a plausible prebiotic reaction. J. Am. Chem. Soc. 129:9556-57
10. Bernal JD. 1949. The physical basis of life. Proc. Phys. Soc. Sect. A 62:537-58
11. Berndt ME, Allen DE, Seyfried WE. 1996. Reduction of CO2 during serpentinization of olivine at 300C and 500 bar. Geology 24:351-54
12. Bernhardt G, Ludemann H, Jaenicke R, König H, Stetter KO. 1984. Biomolecules are unstable under "black smoker" conditions. Naturwissenschaften 71:583-86
13. Breslow R. 1959. On the mechanism of the formose reaction. Tetrahedron Lett. 21:22-26
14. Butlerow A. 1861. Formation synthetique d'une substance sucrée. C. R. Acad. Sci. 53:145-47(In French)
15. Cairns-Smith A, Ingram P, Walker G. 1972. Formose production by minerals: possible relevance to the origin of life. J. Theor. Biol. 35:601-4
16. Chyba C, Sagan C. 1992. Endogenous production, exogenous delivery and impact-shock synthesis of organic molecules: an inventory for the origins of life. Nature 355:125-32
17. Cleaves HJ. 2008 The prebiotic geochemistry of formaldehyde. Precambr. Res. 164:111-18
18. Cleaves HJ. 2010. The origin of the biologically coded amino acids. J. Theor. Biol. 263:490-98
19. Cleaves HJ, Chalmers JH, Lazcano A, Miller SL, Bada JL. 2008 A reassessment of prebiotic synthesis in neutral planetary atmospheres. Orig. Life Evol. Biosph. 38:105-15
20. Cleaves HJ, Nelson KE, Miller SL. 2006. The prebiotic synthesis of pyrimidines in frozen solution. Naturwissenschaften 93:228-31
21. Corliss JB, Baross JA, Hoffman SE. 1981. An hypothesis concerning the relationship between submarine hot springs and the origin of life on Earth. Oceanol. Acta 4(Suppl.):59-69
22. Deamer D, Dworkin JP, Sandford SA, Bernstein MP, Allamandola LJ. 2002. The first cell membranes. Astrobiology 2:371-81
23. Decker P, Schmeer H, Pohlmann R. 1982. Identification of formose sugars, presumable prebiotic metabolites, using capillary gas chromatography/gas chromatography-mass spectrometry of n-butoxime trifluoroacetates on OV-225. J. Chromatogr. 244:281-91
24. Drobner E, Huber H, Wachtershauser G, Rose D, Stetter KO. 1990. Pyrite formation linked with hydrogen evolution under anaerobic conditions. Nature 346:742-44
25. Engelhart AE, Hud NV. 2010. Primitive genetic polymers. Cold Spring Harb. Perspect. Biol. doi: 10.1101/ cshperspect.a002196
26. Ferris JP, Sanchez RA, Orgel LE. 1968. Studies in prebiotic synthesis. III. Synthesis of pyrimidines from cyanoacetylene and cyanate. J. Mol. Biol. 33:693-704
27. Ferris JP, Zamek OS, Altbuch AM, Freiman H. 1974. Chemical evolution. XVIII. Synthesis of pyrimidines from guanidine and cyanoacetaldehyde. J. Mol. Evol. 3:301-9
28. Folsome C, Brittain A, Smith A, Chang S. 1981. Hydrazines and carbohydrazides produced from oxidized carbon in Earth's primitive environment. Nature 294:64-65
29. Foustoukos DI, SeyfriedWE. 2004. Hydrocarbons in hydrothermal vent fluids: the role of chromium-bearing catalysts. Science 304:1002-5
30. Fox SW, Harada K. 1961. Synthesis of uracil under conditions of a thermal model of prebiological chemistry. Science 133:1923-24
31. Fox SW, Windsor CR. 1970. Synthesis of amino acids by the heating of formaldehyde and ammonia. Science 170:984-86
32. Fu Q, Sherwood Lollar B, Horita J, Lacrampe-CouloumeG, SeyfriedWE. 2007. Abiotic formation of hydrocarbons under hydrothermal conditions:Constraints from chemical and isotope data. Geochim. Cosmochim. Acta 71:1982-98
33. FullerWP, Sanchez RA, Orgel LE. 1972a. Studies in prebiotic synthesis. VI. Synthesis of purine nucleosides. J. Mol. Biol. 67:25-33
34. Fuller WP, Sanchez RA, Orgel LE. 1972b. Studies in prebiotic synthesis. VII. Solid-state synthesis of purine nucleosides. J. Mol. Evol. 1:249-57
35. Gabel NW, Ponnamperuma C. 1967. Synthesis of sugars in potentially prebiotic conditions. Nature 216:455
36. GilbertW. 1986. Origin of life: the RNA world. Nature 319:618
37. Haldane J.B.S. 1954. The origins of life. New Biol. 16:12-27
38. Hargreaves WR, Mulvihill SJ, Deamer DW. 1977. Synthesis of phospholipids and membranes in prebiotic environments. Nature 266:78-80
39. Hayatsu R, Studier MH, Matsuoka S, Anders E. 1972. Origin of organic matter in early solar system-IV. Catalytic synthesis of nitriles, nitrogen bases and porphyrin-like pigments. Geochim. Cosmochim. Acta 36:555-71
40. Hayatsu R, Studier MH, Oda A, Fuse K, Anders E. 1968. Origin of organic matter in early solar system-II. Nitrogen compounds. Geochim. Cosmochim. Acta 32:175-90
41. Hazen RM, Sverjensky DA. 2010. Mineral surfaces, geochemical complexities, and the origins of life. Cold Spring Harb. Perspect. Biol. doi: 10.1101/cshperspect.a002162
42. Heinen W, Lauwers AM. 1996. Organic sulfur compounds resulting from the interaction of iron sulfide, hydrogen sulfide and carbon dioxide in an anaerobic aqueous environment. Orig. Life Evol. Biosph. 26:131- 50
43. Hennet RJ, Holm NG, Engel MH. 1992. Abiotic synthesis of amino acids under hydrothermal conditions and the origin of life: a perpetual phenomenon? Naturwissenschaften 79:361-65
44. Horita J, Berndt ME. 1999. Abiogenic methane formation and isotopic fractionation under hydrothermal conditions. Science 285:1055-57
45. Huber C, W?achtersh?auser G. 1997. Activated acetic acid by carbon fixation on (Fe,Ni)S under primordial conditions. Science 276:245-47
46. Huber C, W?achtersh?auser G. 2006. α-Hydroxy and α-Amino acids under possible Hadean, volcanic originof- life conditions. Science 314:630-32
47. Ji F, Zhou H, Yang Q. 2008 The abiotic formation of hydrocarbons from dissolved CO2 under hydrothermal conditions with cobalt-bearing magnetite. Orig. Life Evol. Biosph. 38:117-25
48. Johnson AP, Cleaves HJ, Dworkin JP, Glavin DP, Lazcano A, Bada JL. 2008 The Miller volcanic spark discharge experiment. Science 322:404
49. Joyce GF. 1989. RNA evolution and the origin of life. Nature 338:217-24
50. Joyce GF. 2002. The antiquity of RNA-based evolution. Nature 418:214-21
51. JoyceGF, Schwartz AW, Miller SL, Orgel LE. 1987. The case for an ancestral genetic system involving simple analogues of the nucleotides. Proc. Natl. Acad. Sci. USA 84:4398-402
52. Kasting JF. 1993. Earth's early atmosphere. Science 259:920-26
53. Keefe AD, Miller SL, McDonald G, Bada J. 1995. Investigation of the prebiotic synthesis of amino acids and RNA bases from CO2 using FeS/H2S as a reducing agent. Proc. Natl. Acad. Sci. USA 92:11904-6
54. LaRowe DE, Regnier P. 2008 Thermodynamic potential for the abiotic synthesis of adenine, cytosine, guanine, thymine, uracil, ribose and deoxyribose in hydrothermal systems. Orig. Life Evol. Biosph. 38:383-97
55. Larralde R, Robertson MP, Miller SL. 1995. Rates of decomposition of ribose and other sugars: implications for chemical evolution. Proc. Natl. Acad. Sci. USA 92:8158-60
56. Lazcano A, Bada JL. 2003. The 1953 Stanley L.Miller Experiment: fifty years of prebiotic organic chemistry. Orig. Life Evol. Biosph. 33:235-42
57. Levy M, Miller SL. 1998. The stability of the RNA bases: implications for the origin of life. Proc. Natl. Acad. Sci. USA 95:7933-38
58. Levy M, Miller SL, Brinton K, Bada JL. 2000. Prebiotic synthesis of adenine and amino acids under Europalike conditions. Icarus 145:609-13
59. Levy M, Miller SL, Oró J. 1999. Production of guanine fromNH4CNpolymerizations. J. Mol. Evol. 49:165-68
60. Li J, Brill TB. 2003. Spectroscopy of hydrothermal reactions, part 26: kinetics of decarboxylation of aliphatic amino acids and comparison with the rates of racemization. Int. J. Chem. Kinet. 35:602-10
61. Loison A, Dubant S, Adam P, Albrecht P. 2010. Elucidation of an iterative process of carbon-carbon bond formation of prebiotic significance. Astrobiology 10:973-88
62. Lowe CU, Rees MW, Markham R. 1963. Synthesis of complex organic compounds from simple precursors: formation of amino-Acids, amino-Acid polymers, fatty acids and purines from ammonium cyanide. Nature 199:219-22
63. Marshall WL. 1994. Hydrothermal synthesis of amino acids. Geochim. Cosmochim. Acta 58:2099-106
64. Martin W, Baross J, KelleyD, Russell MJ. 2008 Hydrothermal vents and the origin of life. Nat. Rev. Microbiol. 6:805-14
65. McCollom TM, Ritter G, Simoneit B.R.T. 1999. Lipid synthesis under hydrothermal conditions by Fischer- Tropsch-Type reactions. Orig. Life Evol. Biosph. 29:153-66
66. McCollom TM, Seewald JS. 2001. A reassessment of the potential for reduction of dissolved CO2 to hydrocarbons during serpentinization of olivine. Geochim. Cosmochim. Acta 65:3769-78
67. McCollom TM, Seewald JS. 2006. Carbon isotope composition of organic compounds produced by abiotic synthesis under hydrothermal conditions. Earth Planet. Sci. Lett. 243:74-84
68. McCollom TM, Seewald JS. 2007. Abiotic synthesis of organic compounds in deep-sea hydrothermal environments. Chem. Rev. 107:382-401
69. Miller SL. 1953. Production of amino acids under possible primitive Earth conditions. Science 117:528-29
70. Miller SL. 1955. Production of some organic compounds under possible primitive Earth conditions. J. Am. Chem. Soc. 77:2351-61
71. Miller SL. 1957. The mechanism of synthesis of amino acids by electric discharges. Biochim. Biophys. Acta 23:480-89
72. Miller SL, Bada JL. 1988. Submarine hot springs and the origin of life. Nature 334:609-11
73. Miller SL, Urey HC. 1959. Organic compound synthesis on the primitive Earth. Science 130:245-51
74. Miyakawa S, Cleaves HJ, Miller SL. 2002a. The cold origin of life: A. Implications based on the hydrolytic stabilities of hydrogen cyanide and formamide. Orig. Life Evol. Biosph. 32:195-208
75. Miyakawa S, Cleaves HJ, Miller SL. 2002b. The cold origin of life: B. Implications based on pyrimidines and purines produced from frozen ammonium cyanide solutions. Orig. Life Evol. Biosph. 32:209-18
76. Miyakawa S, Yamanashi H, Kobayashi K, Cleaves HJ, Miller SL. 2002c. Prebiotic synthesis from CO atmospheres: implications for the origins of life. Proc. Natl. Acad. Sci. USA 99:14628-31
77. Müller D, Pitsch S, Kittaka A, Wagner A, Witner CE, et al. 1990. Chemie von α-Aminonitrilen. Aldomerisierung vonGlycolaldehyd-phosphat zu racemischenHexose-2,4,6-Triphosphaten und (inGegenwart von Formaldehyd) racemischen Pentose-2,4-diphosphaten: rac-Allose-2,4,6-Triphosphat und rac- Ribose-2,4-diphosphat sind die Reaktionshauptprodukte. Helv. Chim. Acta 73:1410-68 (In German)
78. Nagy B, Bitz MC. 1963. Long-chain fatty acids from the Orgueil meteorite. Arch. Biochem. Biophys. 101:240-48
79. Nelson KE, Robertson MP, Levy M, Miller SL. 2001. Concentration by evaporation and the prebiotic synthesis of cytosine. Orig. Life Evol. Biosph. 31:221-29
80. Nielsen PE. 1993. Peptide nucleic acids (PNA): a model structure for the primordial genetic material? Orig. Life Evol. Biosph. 23:323-27
81. Nooner DW, Gilbert JM, Gelpi E, Or ó J. 1976. Closed system Fischer-Tropsch synthesis over meteoritic iron, iron ore and nickel-iron alloy. Geochim. Cosmochim. Acta 40:915-24
82. Nooner DW, Or ó J. 1979. Synthesis of fatty acids by a closed system Fischer-Tropsch process. Hydrocarb. Synth. 12:160-70
83. Oparin AI. 1938. The origin of life. New York: Macmillan Oró J. 1960. Synthesis of adenine from ammonium cyanide. Biochem. Biophys. Res. Commun. 2:407-12
84. Oró J, Kamat SS. 1961. Amino-Acid synthesis from hydrogen cyanide under possible primitive earth conditions. Nature 190:442-43
85. Oró J, Kimball AP. 1961. Synthesis of purines under possible primitive earth conditions. I. Adenine from hydrogen cyanide. Arch. Biochem. Biophys. 94:217-27
86. Oró J, Kimball A, Fritz R, Master F. 1959. Amino acid synthesis from formaldehyde and hydroxylamine. Arch. Biochem. Biophys. 85:115-30
87. Parker ET, Cleaves HJ, Dworkin JP, Glavin DP, Callahan M, et al. 2011. Primordial synthesis of amines and amino acids in a 1958 MillerH2S-rich spark discharge experiment. Proc.Natl. Acad. Sci. USA 108:5526-31
88. Powner MW, Berland B, Sutherland JD. 2009. Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions. Nature 459:239-42
89. Prieur BE. 2001. É tude de l'activité pre'biotique potentielle de l'acide borique. C. R. Acad. Sci. 4:667-70 (In French)
90. Reid C, Orgel LE. 1967. Synthesis of sugars in potentially prebiotic conditions. Nature 216:455
91. Ricardo A, Carrigan MA, Olcott AN, Benner SA. 2004. Borate minerals stabilize ribose. Science 303:196
92. Rickard D, Luther GWIII. 1997. Kinetics of pyrite formation by the H2S oxidation of iron (II) monosulfide in aqueous solutions between 25 and 125C: the mechanism. Geochim. Cosmochim. Acta 61:135-47
93. Roberston MP, Miller SL. 1995. An efficient prebiotic synthesis of cytosine and uracil. Nature 375:772-74
94. Russell MJ, Hall AJ. 2006. The onset and early evolution of life. Geol. Soc. Am. Mem. 198:1-32
95. Rushdi AI, Simoneit B.R.T. 2001. Lipid formation by aqueous Fischer-Tropsch-Type synthesis over a temperature range of 100 to 400C. Orig. Life Evol. Biosph. 31:103-18
96. Saladino R, Ciambecchini U, Crestini C, Costanzo G, Negri R, Di Mauro E. 2003. One-pot TiO2-catalyzed synthesis of nucleic bases and acyclonucleosides from formamide: implications for the origin of life. ChemBioChem 4:514-21
97. Saladino R, Crestini C, Ciambecchini U, Ciciriello F, Costanzo G, Di Mauro E. 2004. Synthesis and degradation of nucleobases and nucleic acids by formamide in the presence of montmorillonites. ChemBioChem 5:1558-66
98. Sanchez R, Ferris J, Orgel LE. 1966a. Conditions for purine synthesis: Did prebiotic synthesis occur at low temperatures? Science 153:72-73
99. Sanchez RA, Ferris JP, Orgel LE. 1966b. Cyanoacetylene in prebiotic synthesis. Science 154:784-85
100. Sanchez RA, Ferris JP, Orgel LE. 1967. Studies in prebiotic synthesis. II. Synthesis of purine precursors and amino acids from aqueous hydrogen cyanide. J. Mol. Biol. 30:223-53
101. Sanchez RA, Orgel LE. 1970. Studies in prebiotic synthesis. V. Synthesis and photoanomerization of pyrimidine nucleosides. J. Mol. Biol. 47:531-43
102. Sanger F, Thompson E.O.P. 1953. The amino-Acid sequence in the glycyl chain of insulin. 1.The identification of lower peptides from partial hydrolysates. Biochem. J. 53:353-66
103. Schlesinger G, Miller SL. 1983. Prebiotic synthesis in atmospheres containing CH4, CO, and CO2. J. Mol. Evol. 19:376-82
104. Schrum JP, Zhu TF, Szostak JW. 2010. The origins of cellular life. Cold Spring Harb. Perspect. Biol. doi: 10.1101/cshperspect.a002212
105. Segre D, Ben-Eli D, Deamer DW, Lancet D. 2001. The lipid world. Orig. Life Evol. Biosph. 31:119-45
106. Shapiro R. 1988. Prebiotic ribose synthesis: a critical analysis. Orig. Life Evol. Biosph. 18:71-85
107. Shapiro R. 1995. The prebiotic role of adenine: a critical analysis. Orig. Life Evol. Biosph. 25:83-98
108. Shapiro R. 1999. Prebiotic cytosine synthesis: a critical analysis and implications for the origin of life. Proc. Natl. Acad. Sci. USA 96:4396-401
109. Strecker A. 1850. Ueber die künstliche Bildung der Milchs?aure und einen neuen, dem Glycocoll homologen Körper. Justus Liebigs Ann. Chem. 75:27-45 (In German)
110. Szostak JW. 2011. An optimal degree of physical and chemical heterogeneity for the origin of life? Philos. Trans. R. Soc. B 366:2894-901
111. Szostak JW, Bartel DP, Luisi PL. 2001. Synthesizing life. Nature 409:387-90
112. Sutherland JD. 2010. Ribonucleotides. Cold Spring Harb. Perspect. Biol. doi: 10.1101/cshperspect.a005439
113. Urey HC. 1952.Onthe chemical history of the Earth and the origin of life. Proc.Natl. Acad. Sci. USA 38:351-63
114. Vallentyne Jr. 1964. Biochemistry of organicmatter-II. Thermal reaction kinetics and transformation products of amino compounds. Geochim. Cosmochim. Acta 28:157-88
115. Vallentyne Jr. 1968. Pyrolysis of proline, leucine, arginine and lysine in aqueous solution. Geochim. Cosmochim. Acta 32:1353-56
116. W?achtershauserG. 1992. Groundworks for an evolutionary biochemistry: the iron-sulfur world. Prog. Biophys. Mol. Biol. 58:85-201
117. Wachtershauser G. 2006. From volcanic origins of chemoautotrophic life to Bacteria, Archaea, and Eukarya. Philos. Trans. R. Soc. B 361:1787-808
118. Watson JD, Crick F.H.C. 1953. Molecular structure of nucleic acids. Nature 171:737-38
119. Yoshino D, Hayatsu R, Anders E. 1971. Origin of organic matter in early solar system-III. Amino acids: catalytic synthesis. Geochim. Cosmochim. Acta 32:175-90
120. Yuasa S, Flory D, Basile B, Oró J. 1984. Abiotic synthesis of purines and other heterocyclic compounds by the action of electrical discharges. J. Mol. Evol. 21:76-80
121. Yuen GU, Kvenvolden KA. 1973. Monocarboxylic acids in Murray and Murchison carbonaceous meteorites. Nature 246:301-3
122. Yuen GU, Lawless JG, Edelson EH. 1981. Quantification of monocarboxylic acids from a spark discharge synthesis. J. Mol. Evol. 17:43-47
123. Zubay G. 1996. Studies on the lead-catalyzed synthesis of aldopentoses. Orig. Life Evol. Biosph. 28:13-26