Abstract
The chemical evolution of biomolecules such as nucleobases and their analogues from simple, one carbon containing molecules under abiotic conditions is a puzzle closely connected to the origin of life. Theoretical elucidation of the abiotic reaction routes leading from basic molecules cyanide acid (HCN) and formamide (H2NCHO) to the formation of purine and adenine is reviewed here. The mechanism of three pathways: from formamide dimer via pyrimidine to purine, from AICN (4-aminoimidazole-5-carboxamidine) to adenine, and from formamide to purine and adenine, are discussed. Based on the comparison of step-by-step mechanism of the reaction pathways, in the addition reaction formamide is suggested to be more reactive than HCN. Beside its simplicity, the formamide self-catalyzed mechanism is energetically more viable than either water-catalyzed mechanism or non-catalyzed process. Moreover, this self-catalyzed mechanism is able to explain the ratio of purine to adenine observed in experiments. The formamide self-catalyzed mechanism for the route leading from formamide to purine and/or adenine is most likely for the formation of adenine (and purine) in the formamide solutions in the early stage of the earth.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Watson JD, Crick FHC (1953) Nature 171:737–738
Watson JD, Crick FHC (1953) Cold Spring Harb Symp Quant Biol 18:123–131
Miller SL (1953) Science 117:528–529
Miller SL, Harold CU (1959) Science 130:245–251
Oró J, Kimball AP (1961) Arch Biochem Biophys 94:217–227
Oró J, Kamat SS (1961) Nature 190:442–443
Saladino R, Crestini C, Costanzo G, Di Mauro E (2005) On the prebiotic synthesis of nucleobases, nucleotides, oligonucleotides, pre-RNA and pre-DNA molecules. In: Walde P. (ed) Topics in current chemistry, “Prebiotic chemistry”, vol 259. Berlin, Springer, pp 29–68
Saladino R, Crestini C, Ciciriello F, Costanzo G, Di Mauro E (2007) Chem Biodivers 4:694–720
Solomon M (1973) Phys Today 26:32–40
Crovisier J (2004) Chap. 8. In: Ehrenfreund P et al (ed) Astrobiology: future perspectives, Astrophysics and space science library, vol 305. Kluwer/Springer, Dordrecht, pp 179–203
Bockelee-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) Astron Astrophys 353:1101–1114
Schutte WA, Boogert ACA, Tielens AGGM, Whittet DCB, Gerakines PA, Chiar JE, Ehrenfreund P, Greenberg JM, van Dishoeck EF, de Graauw T (1999) Astron Astrophys 343:966–976
Bredereck H, Effenberger F, Rainer G, Schosser HP (1962) Justus Liebigs Ann Chem 659:133–138
Yamada H, Okamoto T (1972) Chem Pharm Bull 20:623–624
Saladino R, Botta G, Pino S, Costanzo G, Di Mauro E (2012) Biochimie 94:1451–1456
Saladino R, Crestini C, Pino S, Costanzo G, Di Mauro E (2012) Phys Life Rev 9:84–104
Saladino R, Crestini C, Costanzo G, Negri R, Di Mauro E (2001) Bioorg Med Chem 9:1249–1253
Saladino R, Crestini C, Costanzo G, Di Mauro E (2004) Curr Org Chem 8:1425–1443
Saladino R, Ciambecchini U, Crestini C, Costanzo G, Negri R, Di Mauro E (2003) Chem Biol Chem 4:514–521
Saladino R, Crestini C, Ciambecchini U, Ciciriello F, Costanzo G, Di Mauro E (2004) Chem Biol Chem 5:1558–1566
Senanayake SD, Idriss H (2006) Proc Natl Acad Sci U S A 103:1194–1198
Bark HL, Buckley R, Grieves GA, Di Mauro E, Hud NV, Orlando TM (2010) Chem Biol Chem 11:1240–1243
Hudson JS, Eberle JF, Vachhani RH, Rogers LC, Wade JH, Krishnamurthy R, Springsteen G (2012) Angew Chem Int Ed 51:5134–5137
Yamada H, Hirobe M, Higashiyama K, Takahashi H, Suzuki KT (1978) J Am Chem Soc 100:4617–4618
Ochiai M, Marumoto R, Kobayashi S, Shimazu H, Morita K (1968) Tetrahedron 24:5731–5737
Yamada H, Hirobe M, Higashiyama K, Takahashi H, Suzuki KT (1978) Tetrahedron Lett 19:4039–4042
Yamada H, Hirobe M, Okamoto T (1980) Yakugaku Zasshi 100:489–492
Shuman RF, Shearin WE, Tull RJ (1979) J Org Chem 44:4532–4536
Sponer JE, Mladek A, Sponer J, Fuentes-Cabrera M (2012) J Phys Chem A 116:720–726
Oró J (1960) Biochem Biophys Res Commun 2:407–412
Oró J (1961) Nature 191:1193–1194
Sanchez RA, Ferris JP, Orgel LE (1967) J Mol Biol 30:223–253
Ferris JP, Orgel L (1966) J Am Chem Soc 88:1074
Sanchez RA, Ferris JP, Orgel LE (1968) J Mol Biol 38:121–128
Ferris JP, Orgel LE (1965) J Am Chem Soc 87:4976–4977
Ferris JP, Orgel LE (1966) J Am Chem Soc 88:3829–3831
Becke AD (1993) J Chem Phys 98:5648–5652
Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785–789
Miehlich B, Savin A, Stoll H, Preuss H (1989) Chem Phys Lett 157:200–206
Scuseria GE, Schaefer HF III (1989) J Chem Phys 90:3700–3703
Scuseria GE, Janssen CL, Schaefer HF III (1988) J Chem Phys 89:7382–7387
Pople JA, Head-Gordon M, Raghavachari K (1987) J Chem Phys 87:5968–5975
Roy D, Najafian K, von Schleyer R (2007) Proc Natl Acad Sci U S A 104:17272–17277
Wang J, Gu J, Nguyen MT, Springsteen G, Leszczynski J (2013) J Phys Chem B 117:2314–2320
Wang J, Gu J, Nguyen MT, Springsteen G, Leszczynski J (2013) J Phys Chem B 117:9333–9342
Hehre WJ, Radom L, Schleyer PR, Pople JA (1986) Ab initio molecular orbital theory. Wiley, New York
Cossi M, Rega N, Scalmani G, Barone VJ (2003) Comput Chem 24:669–681
Barone V, Cossi M (1998) J Phys Chem A102:1995–2001
Cossi M, Barone V, Cammi R, Tomasi J (1996) Chem Phys Lett 255:327–335
Miertus S, Scrocco E, Tomasi J (1981) Chem Phys 55:117–129
Nguyen VS, Abbott HL, Dawley MM, Orlando TM, Leszczynski J, Nguyen MT (2011) J Phys Chem A 115:841–851
Nguyen VS, Orlando TM, Leszczynski J, Nguyen MT (2013) J Phys Chem A 117:2543–2555
Moore ML (1949) In: Adams R, Bachmann WE, Blatt AH, Fieser LF, Johnson JR (eds) Organic reactions, vol 5. Wiley, New York, pp 301–330
Wang J, Gu J, Nguyen MT, Springsteen G, Leszczynski J (2013) J Phys Chem B 117:14039–14045
Acknowledgements
This work was jointly supported by NSF and the NASA Astrobiology Program under the NSF Center for Chemical Evolution, CHE1004570. We would like to thank the Mississippi Center for Supercomputing Research for a generous allotment of computer time.
Author information
Authors and Affiliations
Corresponding authors
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer Science+Business Media New York
About this chapter
Cite this chapter
Wang, J., Gu, J., Leszczynski, J. (2014). Hints from Computational Chemistry: Mechanisms of Transformations of Simple Species into Purine and Adenine by Feasible Abiotic Processes. In: Leszczynski, J., Shukla, M. (eds) Practical Aspects of Computational Chemistry III. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-7445-7_12
Download citation
DOI: https://doi.org/10.1007/978-1-4899-7445-7_12
Published:
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4899-7444-0
Online ISBN: 978-1-4899-7445-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)