Primordial oil slick and the formation of hydrophobic tetrapyrrole macrocycles

Astrobiology

Volumn 12, Issue 11, 2012, Pages 1055-1068

  Soares, Ana R M ^a   Taniguchi, Masahiko ^a   Chandrashaker, Vanampally ^a   Lindsey, Jonathan S ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OIL; PORPHYRIN; TETRAPYRROLE DERIVATIVE; WATER;

ARTICLE; CHEMICAL PHENOMENA; CHEMISTRY; KINETICS; PH; PHOTOSYNTHESIS; SOLUTION AND SOLUBILITY; SYNTHESIS;

HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; KINETICS; OILS; PHOTOSYNTHESIS; PORPHYRINS; SOLUTIONS; TETRAPYRROLES; WATER;

EID: 84868383598     PISSN: 15311074     EISSN: None     Source Type: Journal    
DOI: 10.1089/ast.2012.0857     Document Type: Article

References (75)

1. Adam, I., Orain, D., and Meier, P. (2004) Concise synthesis of 1H-pyrazin-2-ones and 2-aminopyrazines. Synlett 2004:2031- 2033
2. Apel, C.L., Deamer, D.W., and Mautner, M.N. (2002) Selfassembled vesicles of monocarboxylic acids and alcohols: Conditions for stability and for the encapsulation of biopolymers. Biochim Biophys Acta 1559:1-9
3. Avissar, Y.J. and Moberg, P.A. (1995) The common origins of the pigments of life - early steps of chlorophyll biosynthesis. Photosynth Res 44:221-242
4. Beale, S.I., Gold, M.H., and Granick, S. (1979) Chemical synthesis of 4,5-dioxovaleric acid and its nonenzymatic transamination to 5-aminolevulinic acid. Phytochemistry 18:441-444
5. Bothner-By, A.A., Dadok, J., Johnson, T.E., and Lindsey, J.S. (1996) Molecular dynamics of covalently-linked multiporphyrin arrays. J Phys Chem 100:17551-17557
6. Chan, Y.A., Podevels, A.M., Kevany, B.M., and Thomas, M.G. (2009) Biosynthesis of polyketide synthase extender units. Nat Prod Rep 26:90-114
7. Chang, S. (1993) Prebiotic synthesis in planetary environments. In The Chemistry of Life's Origins, Vol. 416, edited by J.M.
8. Greenberg, C.X. Mendoza-Go'mez, and V. Pirronello, NATO ASI Series C: Mathematical and Physical Sciences, Kluwer Academic Publishers, Dordrecht, pp 259-299
9. Cleaves, H.J. and Miller, S.L. (1998) Oceanic protection of prebiotic organic compounds from UV radiation. Proc Natl Acad Sci USA 95:7260-7263
10. Coster, H.G.L. (2003) Dielectric and electrical properties of lipid bilayers in relation to their structure. In Planar Lipid Bilayers (BLM) and their Applications, edited by H.T. Tien and A. Ottova- Leitmannova, Elsevier, Amsterdam, pp 75-108
11. de Duve, C. (1991) Blueprint for a Cell: The Nature and Origin of Life, Carolina Biological Supply Company, Neil Patterson Publishers, Burlington, NC, pp 133-136
12. Dobson, C.M., Ellison, G.B., Tuck, A.F., and Vaida, V. (2000) Atmospheric aerosols as prebiotic chemical reactors. Proc Natl Acad Sci USA 97:11864-11868
13. Ehrenfreund, P., Rasmussen, S., Cleaves, J., and Chen, L. (2006) Experimentally tracing the key steps in the origin of life: The aromatic world. Astrobiology 6:490-520
14. Eschenmoser, A. (1988) Vitamin B12: Experiments concerning the origin of its molecular structure. Angew Chem Int Ed Engl 27:5-39
15. Eschenmoser, A. (2007a) The search for the chemistry of life's origin. Tetrahedron 63:12821-12844
16. Eschenmoser, A. (2007b) On a hypothetical generational relationship between HCN and constituents of the reductive citric acid cycle. Chem Biodivers 4:554-573
17. Geier, G.R., III, and Lindsey, J.S. (2001) Investigation of porphyrin-forming reactions. Part 2. Examination of the reaction course in two-step, one-flask syntheses of mesosubstituted porphyrins. J Chem Soc Perkin Trans 2, 687-700
18. Granick, S. (1950) The structural and functional relationships between heme and chlorophyll. Harvey Lect 44:220-245
19. Guzman, M.I. and Martin, S.T. (2008) Oxaloacetate-to-malate conversion by mineral photoelectrochemistry: Implications for the viability of the reductive tricarboxylic acid cycle in prebiotic chemistry. Int J Astrobiol 7:271-278
20. Holliday, G.L., Thornton, J.M., Marquet, A., Smith, A.G., Ré- beillé, F., Mendel, R., Schubert, H.L., Lawrence, A.D., and Martin, M.J. (2007) Evolution of enzymes and pathways for the biosynthesis of cofactors. Nat Prod Rep 24:972-987
21. Huang, Y., Wang, Y., Alexandre, M.R., Lee, T., Rose-Petruck, C., Fuller, M., and Pizzarello, S. (2005) Molecular and compoundspecific isotopic characterization of monocarboxylic acids in carbonaceous meteorites. Geochim Cosmochim Acta 69: 1073-1084
22. Hud, N.V. and Anet, F.A.L. (2000) Intercalation-mediated synthesis and replication: A new approach to the origin of life. J Theor Biol 205:543-562
23. Jaffé, H.H. and Orchin, M. (1962) Theory and Applications of Ultraviolet Spectroscopy, John Wiley and Sons, Inc., New York, pp 178-182
24. Jeandon, C. and Callot, H.J. (1993) Cyclotetramerization of modified Knorr pyrroles into porphyrins. A reinvestigation. Bull Soc Chim Fr 13:625-629
25. Keefe, A.D., Newton, G.L., and Miller, S.L. (1995) A possible prebiotic synthesis of pantetheine, a precursor to coenzyme A. Nature 373:683-685
26. Komiya, M. and Shimoyama, A. (1996) Organic compounds from insoluble organic matter isolated from the Murchison carbonaceous chondrite by heating experiments. Bull Chem Soc Jpn 69:53-58
27. Lahav N. (1999) Biogenesis - Theories of Life's Origin, Oxford University Press, New York, pp 160-162
28. Lasaga, A.C., Holland, H.D., and Dwyer, M.J. (1971) Primordial oil slick. Science 174:53-55
29. Lawless, J.G. and Yuen, G.U. (1979) Quantification of monocarboxylic acids in the Murchison carbonaceous meteorite. Nature 282:396-398
30. Lee, C.-H., Li, F., Iwamoto, K., Dadok, J., Bothner-By, A.A., and Lindsey, J.S. (1995) Synthetic approaches to regioisomerically pure porphyrins bearing four different meso-substituents. Tetrahedron 51:11645-11672
31. Li, F., Yang, K., Tyhonas, J.S., MacCrum, K.A., and Lindsey, J.S. (1997) Beneficial effects of salts on an acid-catalyzed condensation leading to porphyrin formation. Tetrahedron 53:12339- 12360
32. Lindsey, J.S. (2000) Synthesis of meso-substituted porphyrins. In The Porphyrin Handbook, Vol. 1, edited by K.M. Kadish, K.M. Smith, and R. Guilard, Academic Press, San Diego, CA, pp 45- 118
33. Lindsey, J.S. and Wagner, R.W. (1989) Investigation of the synthesis of ortho-substituted tetraphenylporphyrins. J Org Chem 54:828-836
34. Lindsey, J.S., Schreiman, I.C., Hsu, H.C., Kearney, P.C., and Marguerettaz, A.M. (1987) Rothemund and Adler-Longo reactions revisited: Synthesis of tetraphenylporphyrins under equilibrium conditions. J Org Chem 52:827-836
35. Lindsey, J.S., MacCrum, K.A., Tyhonas, J.S., and Chuang, Y.-Y. (1994) Investigation of a synthesis of meso-porphyrins employing high concentration conditions and an electron transport chain for aerobic oxidation. J Org Chem 59:579-587
36. Lindsey, J.S., Ptaszek, M., and Taniguchi, M. (2009) Simple formation of an abiotic porphyrinogen in aqueous solution. Orig Life Evol Biosph 39:495-515
37. Lindsey, J.S., Chandrashaker, V., Taniguchi, M., and Ptaszek, M. (2011) Abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants. New J Chem 35:65-75
38. Martin, W. and Russell, M.J. (2007) On the origin of biochemistry at an alkaline hydrothermal vent. Philos Trans R Soc Lond B Biol Sci 362:1887-1925
39. Mauzerall, D. (1960) The thermodynamic stability of porphyrinogens. J Am Chem Soc 82:2601-2605
40. Mauzerall, D. (1962) The photoreduction of porphyrins: Structure of the products. J Am Chem Soc 84:2437-2445
41. Mauzerall, D. (1976) Chlorophyll and photosynthesis. Philos Trans R Soc Lond B Biol Sci 273:287-294
42. Mauzerall, D. and Granick, S. (1958) Porphyrin biosynthesis in erythrocytes III. Uroporphyrinogen and its decarboxylase. J Biol Chem 232:1141-1162
43. Mauzerall, D. and Sun, K. (2003) Photoinduced charge separation in lipid bilayers. In Planar Lipid Bilayers (BLM) and Their Applications, edited by H.T. Tien and A. Ottova-Leitmannova, Elsevier, Amsterdam, pp 963-979
44. Mauzerall, D.C. (1990) The photochemical origins of life and photoreaction of ferrous ion in the Archaean oceans. Orig Life Evol Biosph 20:293-302
45. Mauzerall, D.C. (1998) Evolution of porphyrins. Clin Dermatol 16:195-201
46. Mercer-Smith, J.A. and Mauzerall, D.C. (1984) Photochemistry of porphyrins: A model for the origin of photosynthesis. Photochem Photobiol 39:397-405
47. Mercer-Smith, J.A., Raudino, A., and Mauzerall, D.C. (1985) A model for the origin of photosynthesis-III. The ultraviolet photochemistry of uroporphyrinogen. Photochem Photobiol 42:239-244
48. Miller, S.L. and Orgel L.E. (1974) The Origins of Life on the Earth, Prentice-Hall, Inc., Englewood Cliffs, NJ, pp 185-188
49. Morton, M.A. and Rosney, W.C.V. (1926) XCVII.-Absorption spectra and tautomerism. Part I. Keto-enol tautomerisation. Ethyl acetoacetate, acetylacetone, and a-benzoylcamphor. J Chem Soc 129:706-713
50. Moss, G.P. (1987) Nomenclature of tetrapyrroles. Pure Appl Chem 59:779-832
51. Nguyen, L.T. and Smith, K.M. (1996) Syntheses of type-I porphyrins via monopyrrole tetramerization. Tetrahedron Lett 37:7177-7180
52. Nilson, F.P.R. (2002) Possible impact of a primordial oil slick on atmospheric and chemical evolution. Orig Life Evol Biosph 32:247-253
53. Olson, J.M. and Pierson, B.K. (1987) Origin and evolution of photosynthetic reaction centers. Orig Life 17:419-430
54. Orgel, L.E. (2008) The implausibility of metabolic cycles on the prebiotic Earth. PLoS Biol 6, e18
55. Owen, O.E., Kalhan, S.C., and Hanson, R.W. (2002) The key role of anaplerosis and cataplerosis for citric acid cycle function. J Biol Chem 277:30409-30412
56. Pichon-Santander, C. and Scott, A.I. (2002) Studies on the tetramerization of substituted monopyrroles to type I porphyrins. Tetrahedron Lett 43:6967-6969
57. Riddick, J.A. and Bunger, W.B. (1970) Organic Solvents. Physical Properties and Methods of Purification, 3rd ed., Wiley-Interscience, New York
58. Rimington, C. (1960) Spectral-absorption coefficients of some porphyrins in the Soret-band region. Biochem J 75:620-623
59. Rimington, C. and Benson, A. (1967) Partition of porphyrins between cyclohexanone and aqueous sodium acetate as a function of pH. Biochem J 105:1085-1090
60. Ross, D.S. (2008) A quantitative evaluation of the iron-sulfur world and its relevance to life's origins. Astrobiology 8:267-272
61. Scheer, H. (2003) The pigments. In Light-Harvesting Antennas in Photosynthesis, edited by B.R. Green and W.W. Parson, Kluwer Academic Publishers, Dordrecht, pp 29-81
62. Scheer, H. (2006) An overview of chlorophylls and bacteriochlorophylls: biochemistry, biophysics, functions and applications. In Chlorophylls and Bacteriochlorophylls. Biochemistry, Biophysics, Functions and Applications, Vol. 25, edited by B
63. Grimm, R.J. Porra, W. Rü diger, and H. Scheer, Advances in Photosynthesis and Respiration, Springer, Dordrecht, pp 1-26
64. Sephton, M.A. (2002) Organic compounds in carbonaceous meteorites. Nat Prod Rep 19:292-311
65. Sivash, A.A., Masinovsky, Z., and Lozovaya, G.I. (1991) Surfactant micelles containing protoporphyrin IX as models of primitive photocatalytic systems: A spectral study. Biosystems 25:131-140
66. Smith, S. and Tsai, S.-C. (2007) The type I fatty acid and polyketide synthases: A tale of two megasynthases. Nat Prod Rep 24:1041-1072
67. Soares, A.R.M., Taniguchi, M., Chandrashaker, V., and Lindsey, J.S. (2012) Self-organization of tetrapyrrole constituents to give a photoactive protocell. Chem Sci 3:1963-1974
68. Sun, K. and Mauzerall, D. (1996) A simple light-driven transmembrane proton pump. Proc Natl Acad Sci USA 93:10758- 10762
69. Taniguchi, M. and Lindsey, J.S. (2012a) Diversity, isomer composition, and design of combinatorial libraries of tetrapyrrole macrocycles. J Porphyr Phthalocyanines 16:1-13
70. Taniguchi, M. and Lindsey J.S. (2012b) Enumeration of isomers of substituted tetrapyrrole macrocycles: From classical problems in biology to modern combinatorial libraries. In Handbook of Porphyrin Science, Vol. 23, edited by K.M. Kadish, K.M. Smith, and R. Guilard, World Scientific, Singapore, pp 1-80
71. Taniguchi, M., Du, H., and Lindsey, J.S. (2011) Virtual libraries of tetrapyrrole macrocycles. Combinatorics, isomers, product distributions, and data mining. J Chem Inf Model 51:2233- 2247
72. Taniguchi, M., Soares, A.R.M., Chandrashaker, V., and Lindsey, J.S. (2012) Tandem combinatorial model for the prebiogenesis of diverse tetrapyrrole macrocycles. New J Chem 36:1057-1069
73. Tien, H.T. (1974) Bilayer Lipid Membranes (BLM): Theory and Practice, Marcel Dekker, New York.
74. Tuck, A. (2002) The role of atmospheric aerosols in the origin of life. Surveys in Geophysics 23:379-409
75. Wä chtershä user, G. (2006) From volcanic origins of chemoautotrophic life to Bacteria, Archaea and Eukarya. Philos Trans R Soc Lond B Biol Sci 361:1787-1808