Prebiotic synthesis of diaminopyrimidine and thiocytosine

Journal of Molecular Evolution

Volumn 43, Issue 6, 1996, Pages 543-550

  Robertson, Michael P ^a,b   Levy, Matthew ^a   Miller, Stanley L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

Cyanoacetaldehyde; Drying lagoons; Guanidine; Pyrimidine synthesis; Thiourea

Indexed keywords

CYTOSINE; CYTOSINE DERIVATIVE; GUANIDINE; PYRIMIDINE DERIVATIVE; THIOUREA; URACIL;

ARTICLE; EVAPORATION; HUMIDITY; HYDROLYSIS; LAGOON; PH; PYRIMIDINE SYNTHESIS;

NASA DISCIPLINE EXOBIOLOGY; NON-NASA CENTER;

ACETALDEHYDE; CYTOSINE; EVOLUTION, MOLECULAR; GUANIDINE; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; PYRIMIDINES; SEAWATER; SOLUBILITY; TEMPERATURE; THIOUREA; URACIL;

EID: 0030457315     PISSN: 00222844     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02202102     Document Type: Article

References (26)

1. Elvers B et al. (eds) (1989) Ullmann's encyclopedia of industrial chemistry, vol A12. 5th ed. VHC, New York, p 546
2. Fabbrizzi L, Micheloni M, Paoletti P, Schwarzenbach G (1977) Protonation process of unusual exothermicity. J Am Chem Soc 99: 5574-5576
3. 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
4. Ferris JP, Goldstein G, Beaulieu DJ (1970) Chemical evolution IV. An evaluation of cyanovinyl phosphate as a prebiotic phosphorylating agent. J Am Chem Soc 92:6598-6603
5. Ferris JP, Zamek OS, Altbuch AM, Freiman H (1974) Chemical evolution XVIII. Synthesis of pyrimidines from guanidine and cyanoacetaldehyde. J Mol Evol 3:301-309
6. Fuller WD, Sanchez RA, Orgel LE (1972) Studies in prebiotic synthesis VII. Solid-state synthesis of purine nucleasides. J Mol Evol 1:249-257
7. Fox SW, Dose K (1972) Molecular evolution and the origin of life. WH Freeman, San Francisco
8. Frost AA, Pearson RG (1961) Kinetics and mechanism. John Wiley, New York, pp 166-169
9. Garrett ER, Tsau J (1972) Solvolyses of cytosine and cytidine. J Pharm Sci 61:1052-1061
10. Keefe AD, Newton GL, Miller SL (1995) A possible prebiotic synthesis of pantetheine, a precursor to coenzyme A. Nature 373:683-685
11. Kirk RE, Othmer DF (1951) Encyclopedia of chemical technology, vol. 7. Interscience Encyclopedia, New York, p 326
12. Limbach PA, Crain PF, McCloskey JA (1994) Summary: the modified nucleosides of RNA. Nucleic Acids Res 22:2183-2196
13. Lohrmann R (1972) Formation of urea and guanidine by irradiation of ammonium cyanide. J Mol Evol 1:263-269
14. 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 199:219-222
15. Miller SL (1957) The mechanism of synthesis of amino acids by electric discharges. Biochim Biophys Acta 23:480-489
16. Miller SL, Orgel LE (1974) The origins of life on the earth. Prentice-Hall, Englewood Cliffs, NJ, pp 129-134
17. Piccirilli JA, Krauch T, Moroney SE, Benner SA (1990) Enzymatic incorporation of a new base pair into DNA and RNA extends the genetic alphabet. Nature 343:33-37
18. Reid EE (1963) Organic chemistry of bivalent sulfur. vol. 5. Chemical Publishing Co. Inc., New York, pp 11-17
19. Robertson MP, Miller SL (1995a) An efficient prebiotic synthesis of cytosine and uracil. Nature 375:772-774
20. Robertson MP, Miller SL (1995b) Prebiotic synthesis of 5-substituted uracils: a bridge between the RNA world and the DNA-protein world. Science 268:702-705
21. Sanchez, RA, Ferris JP, Orgel LE (1966) Cyanoacetylene in prebiotic synthesis. Science 154:784-785
22. Shapiro R (1995) The prebiotic role of adenine: a critical analysis. Orig Life Evol Biosph 25:83-98
23. Shapiro R, Klein RS (1966) The deamination of cytidine and cytosine by acidic buffer solutions. Mutagenic implications. Biochemistry 5:2358-2362
24. Shaw WHR, Walker DG (1958) Kinetic studies of thiourea derivatives. IV. The methylated thioureas. Conclusions. J Am Chem Soc 80: 5337-5342
25. Shnidman L (1933) The solubility of thiourea in water, methanol, and ethanol. J Phys Chem 37:693-700
26. Switzer C, Moroney SE, Benner SA (1989) Enzymatic incorporation of a new base pair into DNA and RNA. J Am Chem Soc 111:8322-8323