Catalytic effects of Murchison Material: Prebiotic Synthesis and Degradation of RNA Precursors

Origins of Life and Evolution of Biospheres

Volumn 41, Issue 5, 2011, Pages 437-451

  Saladino, Raffaele ^a   Crestini, Claudia ^b   Cossetti, Cristina ^c   Di Mauro, Ernesto ^c   Deamer, David ^d  

^a UNIVERSITY OF TUSCIA   (Italy)

^b UNIVERSITY OF ROME TOR VERGATA   (Italy)

^c SAPIENZA UNIVERSITY OF ROME   (Italy)

^d University of California Santa Cruz   (United States)

Author keywords

Catalysis; Formamide; Murchison meteorite; Prebiotic chemistry

Indexed keywords

AMINO ACID; CARBON; CARBOXYLIC ACID; FORMAMIDE; FORMAMIDE DERIVATIVE; PURINE DERIVATIVE; PYRIMIDINE DERIVATIVE; RNA; WATER;

AMINO ACID; CATALYSIS; CONDENSATION; DEGRADATION; EARLY EARTH; HYDROLYSIS; MURCHISON METEORITE; ORIGIN OF LIFE; PH; THERMOPHILY;

ARTICLE; ASTRONOMY; BIOGENESIS; CATALYSIS; CHEMISTRY; HALF LIFE TIME; HYDROLYSIS; KINETICS; MASS FRAGMENTOGRAPHY; PH; RNA STABILITY; SYNTHESIS;

AMINO ACIDS; BIOGENESIS; CARBON; CARBOXYLIC ACIDS; CATALYSIS; EARTH (PLANET); FORMAMIDES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HALF-LIFE; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; KINETICS; METEOROIDS; PURINES; PYRIMIDINES; RNA; RNA STABILITY; WATER;

EID: 80052966312     PISSN: 01696149     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11084-011-9239-0     Document Type: Article

References (57)

1. Aizpurua JM, Palomo C (1983) Reagents and synthetic methods 30. Practical and improved method for formylating amino compounds by means of formic acid-dimethylformamide system. Synth Commun 13: 745-752.
2. Bibillo A, Figlerowicz M, Kierzek R (1999) The non-enzymatic hydrolysis of oligoribonucleotides. VI. The role of biogenic polyamines. Nucleic Acids Res 27: 3931-3937.
3. Bockelée-Morvan D, Lis DC, Wink JE, Despois D, Crovisier J, Bachiller R, Benford DJ, Biver N, Colom P, Davies JK, Gérard E, Germain B, Houde M, Mehringer D, Moreno R, Paubert G, Phillips TG, Rauer H (2000) New molecules found in Comet C/1995 O1 (Hale-Bopp). Investigating the link between cometary and interstellar material. Astron Astrophys 353: 1101-1114.
4. Bredereck H, Ulmer H, Waldman H (1956) Synthesis in the purine series VII. Purine from formamide. Methylation and bromination of purine. Chem Ber 89: 12-18.
5. Bredereck H, Gompper R, Schuh HGV, Theilig G (1959) Neuere Methoden der preparativen organischen Chemie II. 16. Synthesen mit ureamiden, ins besondere mit formamid. Angew Chem 71: 753.
6. Campins H, Hargrove K, Pinilla-Alonso N, Howell ES, Kelley MS, Licandro J, Mothé-Diniz T, Fernández J, Ziffer J (2010) Water ice and organics on the surface of the asteroid 24 Themis. Nature 464: 1320-1321.
7. Cech TR (1987) The chemistry of self-splicing RNA and RNA enzymes. Science 236: 1532-1539.
8. Cheng LK, Unrau PJ (2010) Closing the circle: replicating RNA with RNA. In: Deamer D, Szostak J (eds) Origins of Life. Cold Spring Harbor Press, New York.
9. Ciciriello F, Costanzo G, Pino S, Crestini C, Saladino R, Di Mauro E (2008) Molecular complexity favours the evolution of ribopolymers. Biochemistry 47: 2732-2742.
10. Cody GD, Scott JH (2007) The Roots of Metabolism. In Sullivan W, Baross J, (eds) Planets & Life. Cambridge University Press, 174-186.
11. Cossetti C, Crestini C, Saladino R, Di Mauro E (2010) Borate minerals and RNA stability. Polymers 2: 211-228.
12. Costanzo G, Pino S, Ciciriello F, Di Mauro E (2009) Generation of long RNA chains in water. J Biol Chem 284: 33206-33216.
13. Ehrenfreund P, Cami J (2010) Cosmic carbon chemistry: From the interstellar medium to the early Earth. In: Deamer D, Szostak J (eds) Origins of Life. Cold Spring Harbor, New York.
14. Eschenmoser A (2007) Reactions of the HCN-tetramer with Aldehydes. Chem Biodivers 4: 554-573.
15. Ferris JP (2006) Montmorillonite catalyzed formation of RNA oligomers: the possible role of catalysis in the origins of life. Phil Trans R Soc Lond B Biol Sci 361: 1777-1786.
16. Fuchs LH, Olsen E, Jensen KJ (1973) Mineralogy, mineral-chemistry, and composition of the Murchison (C2) meteorite $ Smithsonian contributions to the earth sciences vol. 10. Smithsonian Institution Press, Washington, pp 1-37.
17. Ghosh A, Sween HY (1996) An extended thermal history (100 MA Long) for asteroid 4 Vesta based on radionuclide and collisional heating. Lunar Planet Sci 27: 407-8.
18. Gilbert W (1986) The RNA World. Nature 319: 618.
19. II. Inorg Chem 43: 3386-3393.
20. Holms WH (1987) Control of flux through the citric acid cycle and the glyoxylate bypass in Escherichia coli. Biochem Soc Symp 54: 17-31.
21. Huber C, Wächtershäuser G (2006) α-Hydroxy and α-amino acids under possible hadean, volcanic origin-of-life conditions. Science 314: 630-632.
22. Ivanov C, Vladovska Y (1978) Formation of purine derivatives under conditions possible on the primitive Earth. Dokl Bolg Akad Nauk 31: 1605-1608.
23. Kaukinen U, Lyytikäinen S, Mikkola S, Lönnberg H (2002) The reactivity of phosphodiester bonds within linear single-stranded oligoribonucleotides is strongly dependent on the base sequence. Nucleic Acids Res 30: 468-467.
24. Kawamura K (2001) Comparison of the rates of prebiotic formation and hydrolysis of RNA under hydrothermal environments and its implications on the chemical evolution of RNA. Nucleic Acids Symp Ser 1: 239-240.
25. Kierzek R (1992) Nonenzymatic hydrolysis of oligoribonucleotides. Nucleic Acids Res 20: 5079-5084.
26. Krooss BM, Brothers L, Engel MH (1991) Geochromatography in petroleum migration: a review. Geol Soc 59: 149-163, London, Special Publications.
27. Lane BG, Butler GC (1959) The exceptional resistance of certain oligoribonucleotides to alkaline degradation. Biochim Biophys Act 33: 281-283.
28. Larter S, Bowler B, Clarke E, Wilson C, Moffatt B, Bennett B, Yardley G, Carruthers D (2000) An experimental investigation of geochromatography during secondary migration of petroleum performed under subsurface conditions with a real rock. Geochem Trans 1: 1467-4866.
29. Li Y, Breaker RR (1999) Kinetics of RNA degradation by specific base catalysis of transesterification involving the 2′-hydroxyl group. J Am Chem Soc 121: 5364-5372.
30. Macdougall JD, Lugmair GW, Kerridge JF (1984) Early aqueous activity on primitive meteorite parent bodies. Nature 307: 249-251.
31. Miller SL (1953) A production of amino acids under possible primitive earth conditions. Science 117: 528-529.
32. Miyakawa S, Cleaves HJ, Miller SL (2002) The cold origin of life: a implications based on the hydrolytic stabilities of hydrogen cyanide and formamide. Orig Life Evol Biosph 32: 195-208.
33. Morowitz HJ, Kostelnik J, Yang J, Cody GD (2000) The origin of intermediary metabolism. Proc Natl Acad Sci USA 97: 7704-7708.
34. Morrow JR, Aures K, Epstein DJ (1995) Metal ion promoted attack of an alcohol on a phosphate diester: modelling the role of metal ions in RNA self-splicing reactions. Chem Comm 23: 2431-2432.
35. Perreault DM, Anslyn EV (1997) Unifying the current data on the mechanism of cleavage-transesterification of RNA. Angew Chem Int Ed Engl 36: 432-450.
36. Rajamani S, Vlassov A, Coombs A, Olasagasti F, Deamer DW (2008) Lipid-assisted synthesis of long RNA-like polymers from mononucleotides. Orig Life Evol Biosph 38: 57-74.
37. Raunier S, Chiavassa T, Duvernay F, Borget F, Aycard JP, Dartois E, d'Hendecourt L (2004) Tentative identification of urea and formamide in ISO-SWS infrared spectra of interstellar ices. Astron Astrophys 416: 165-169.
38. Rubin RH, Swenson GW, Benson RC, Tigelaar HL, Flygare WH (1971) Microwave detection of interstellar formamide. Astrophys J 169: L39.
39. Saladino R, Crestini C, Costanzo G, Negri R, Di Mauro E (2001) A Possible prebiotic synthesis of purine, cytosine, and 4(3 H)-pyrimidinone from formamide: implications for the origin of life. Bioorg Med Chem 9: 1249-1253.
40. Saladino R, Crestini C, Ciciriello F, Costanzo G, Negri R, Di Mauro E (2004) A novel synthesis of biomolecules precursors. In: Ehrenfreund P (ed) Astrobiology: Future Perspectives. Netherlands, pp. 393-413.
41. Saladino R, Crestini C, Costanzo G, Di Mauro E (2005) On the prebiotic synthesis of nucleobases, nucleotides, oligonucleotides, pre-RNA and pre-DNA Molecules. Top Curr Chem 259: 29-68.
42. Saladino R, Crestini C, Ciciriello F, Di Mauro E, Costanzo G (2006a) Origin of informational polymers: differential stability of phosphoester bonds in ribo monomers and oligomers. J Biol Chem 281: 5790-5796.
43. Saladino R, Crestini C, Neri V, Ciciriello F, Costanzo G, Di Mauro E (2006b) Origin of informational polymers: the concurrent roles of formamide and phosphates. Chem Bio Chem 7: 1707-1714.
44. Saladino R, Crestini C, Ciciriello F, Costanzo G, Di Mauro E (2007) Formamide chemistry and the origin of informational polymers. Chem Biodivers 4: 694-720.
45. Saladino R, Neri V, Crestini C, Costanzo G, Graciotti M, Di Mauro E (2008) Synthesis and degradation of nucleic acid components by formamide and iron sulfur minerals. J Am Chem Soc 130: 15512-15518.
46. Saladino R, Crestini C, Ciciriello F, Pino S, Costanzo G, Di Mauro E (2009) From formamide to RNA: the roles of formamide and water in the evolution of chemical information. Res Microbiol 160: 441-448.
47. Schmitt-Kopplin P, Gabelicab Z, Gougeonc RD, Feketea A, Kanawatia B, Harira M, Gebefuegia I, Eckeld G, Hertkorna N (2010) High molecular diversity of extraterrestrial organic matter in Murchison meteorite revealed 40 years after its fall. Proc Natl Acad Sci USA 107: 2763-2768.
48. Schutte WA, Boogert ACA, Tielens AGGM, Whittet DCB, Gerakines PA, Chiar JE, Ehrenfreund P, Greenberg JM, van Dishoeck EF, de Graauw T (1999) Weak ice absorption features at 7. 24 and 7. 41 mm in the spectrum of the obscured young stellar object W 33A? Astron Astrophys 343: 966-976.
49. Smith KC, Allen FW (1953) The liberation of polynucleotides by the alkaline hydrolysis of ribonucleic acid from yeast. J Am Chem Soc 75: 2131-2133.
50. Smith E, Morowitz HJ (2004) Universality in intermediary metabolism. Proc Natl Acad Sci USA 101: 13168-13173.
51. Soukup G, Breaker R (1999a) Relationship between internucleotide linkage geometry and the stability of RNA. RNA 5: 1308-1325.
52. Soukup GA, Breaker RR (1999b) Nucleic acid molecular switches. Trends Biotechnol 17: 469-476.
53. Stoks PG, Schwartz AW (1981) Nitrogen-heterocyclic compounds in meteorites: significance and mechanisms of formation. Geochim Cosmochim Acta 45: 563-569.
54. Wing MR, Bada JL (1991) Geochromatography on the parent body of the carbonaceous chondrite Ivuna. Geochim Cosmochim Acta 55: 2937-2942.
55. Yamada H, Okamoto T (1972) A one-step synthesis of purine ring from formamide. Chem Pharm Bull 20: 623.
56. 15N coupling. Tetrahedron Lett 42: 4039-4042.
57. Zhanpeisov NU, Leszczynski J (1999) Specific solvation effects on the structures and properties of Watson-Crick and reverse Watson-Crick isocytosine-cytosine and guanine-cytosine base pairs: a theoretical ab initio study. J Mol Struct THEOCHEM 487: 107-115.