Abstract
From a chemical point of view, it seems likely that peptides and smaller proteins were the first biomolecules which may have formed on the prebiotic Earth. In the presence of sodium chloride and copper ions, amino acids are readily connected to oligomers via the Salt-Induced Peptide Formation (SIPF) reaction mechanism in aqueous solution under locally conceivable primitive Earth conditions. The SIPF reaction shows some specific properties suggesting a close relationship to modern life forms, like a preference for α-amino acids and even stereospecific differentiation in favour of the l-forms of some amino acids. Furthermore, the amino acid sequences which are preferably formed by this reaction can still be found with a probability much above average in proteins of still existing life forms, like archaea and other prokaryotic cells. Once formed, even short peptides have a number of highly interesting abilities pointing towards possible further evolutionary pathways: chain elongation on the surface of clay minerals, formation of nanovesicles with membrane-like structure, autocatalytic self-replication from fragments, stabilisation of phosphate ions against precipitation, etc.
When at a later stage of chemical evolution the RNA/DNA based replication mechanism began to establish, initially it would probably just have reproduced and gradually replaced peptides and proteins which had existed before and already had exerted some biochemical impact on the environment. By splicing preexisting peptides to larger proteins, the complexity and diversity of biomolecules could have undergone a tremendous progress at that period of evolution towards the highly complex life forms populating the Earth nowadays.
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References
Al-Farawati R, van den Berg CMG (1999) Metal-sulfide complexation in seawater. Mar Chem 63:331–352
Andini S, Benedetti E, Ferrara L, Paolillo L, Temussi PA (1975) NMR studies of prebiotic polypeptides. Orig Life Evol Biosph 6:147–153
Bada JL, Lazcano A (2003) Prebiotic soup – revisiting the Miller experiment. Science 300:745–746
Barks HL, Buckley R, Grieves GA, Di Mauro E, Hud NV, Orlando TM (2010) Guanine, adenine, and hypoxanthine production in UV-irradiated formamide solutions: Relaxation of the requirements for prebiotic purine nucleobase formation. Chembiochem 11:1240–1243
Basiuk VA, Gromovoy TY, Golovaty VG, Glukhoy AM (1990) Mechanisms of amino acid polycondensation on silica and alumina surfaces. Orig Life Evol Biosph 20:483–498
Berger R, Quack M (2000) Electroweak quantum chemistry of alanine: parity violation in gas and condensed phase. Chemphyschem 1:57–60
Brack A, Louembe D, Spach G (1975) Polymerization of amino acid methyl esters via their copper complexes. Orig Life 6:407–411
Breslow R (1959) On the mechanism of the formose reaction. Tetrahedron Lett 21:22–26
Bujdak J, Rode BM (1996) The effect of Smectite composition on the catalysis of peptide bond formation. J Mol Evol 43:326–333
Bujdak J, Rode BM (1997) Silica, alumina, and clay-catalyzed alanine peptide bond formation. J Mol Evol 45:457–466
Bujdak J, Rode BM (1999) Silica, alumina and clay catalyzed peptide bond formation: enhanced efficiency of alumina catalyst. Orig Life Evol Biosph 29:451–461
Bujdak J, Rode BM (2001) Activated alumina as an energy source for peptide bond formation: consequences for mineral-mediated prebiotic processes. Amino Acids 21:281–291
Bujdak J, Rode BM (2003) Alumina catalyzed reactions of amino acids. J Therm Anal Calorim 73:797–805
Bujdak J, Slosiarikove H, Texler N, Schwendinger MG, Rode BM (1994) On the possible role of montmorillonite in prebiotic peptide formation. Monatsh Chem 125:1033–1039
Bujdak J, Faybikova K, Eder AH, Yongyai Y, Rode BM (1995) Peptide chain elongation: a possible role of montmorillonite in prebiotic synthesis of protein precursors. Orig Life Evol Biosph 25:431–441
Butlerow AM (1861) Formation synthetique d’une substance sucree. C R Acad Sci 53:145–147
Carny O, Gazit E (2005) A model for the role of short self-assembled peptides in the very early stages of the origin of life. FASEB J 19:1051–1055
Chung N, Lohrmann R, Orgel LE, Rabinowitz J (1971) The mechanism of the trimetaphosphate-induced peptide synthesis. Tetrahedron 27:1205–1210
Cleaves HJ, Miller SL (1998) Oceanic protection of prebiotic organic compounds from UV radiation. Proc Natl Acad Sci USA 95:7260–7263
Cody GD, Boctor NZ, Filley TR, Hazen RM, Scott JH, Sharma A, Yoder HS Jr (2000) Primordial carbonylated iron-sulfur compounds and the synthesis of pyruvate. Science 289:1337–1340
Decker P, Schweer H, Pohlmann R (1982) Bioids: X. Identification of formose sugars, presumable prebiotic metabolites, using capillary gas chromatography/gas chromatography-mass spectrometry of n-butoxime trifluoroacetates on OV-225. J Chromatogr A 244:281–291
Delano JW (2001) Redox history of the Earth’s interior since 3900 Ma: implications for prebiotic molecules. Orig Life Evol Biosph 31:311–341
Dyson F (1999) Origins of life. Cambridge University Press, Cambridge
Eder AH, Rode BM (1994) Influence of alkali- and alkaline-earth-metal cations on the ‘salt-induced peptide formation’ reaction. J Chem Soc Dalton Trans. doi:10.1039/DT9940001125
Eigen M, Schuster P (1977) A principle of natural self-organization. Naturwissenschaften 64:541–565
Eschenmoser A (1999) Chemical etiology of nucleic acid structure. Science 284:2118–2124
Ferris JP (1999) Prebiotic synthesis on minerals: bridging the prebiotic and RNA worlds. Biol Bull 196:311–314
Ferris JP, Hagan WJ Jr (1984) HCN and chemical evolution: the possible role of cyano compounds in prebiotic synthesis. Tetrahedron 40:1093–1120
Ferris JP, Orgel LE (1965) Aminomalononitrile and 4-amino-5-cyanoimidazole in hydrogen cyanide polymerization and adenine synthesis. J Am Chem Soc 87:4976–4977
Ferris JP, Orgel LE (1966) An unusual photochemical rearrangement in the synthesis of adenine from hydrogen cyanide. J Am Chem Soc 88:1074–1074
Ferris JP, Donner DB, Lotz W (1972) The mechanism of the oligomerization of hydrogen cyanide and its possible role in the origins of life. J Am Chem Soc 94:6968–6974
Fitz D, Reiner H, Plankensteiner K, Rode BM (2007) Possible origins of biohomochirality. Curr Chem Biol 1:41–52
Fitz D, Jakschitz T, Rode BM (2008) The catalytic effect of L- and D-histidine on alanine and lysine peptide formation. J Inorg Biochem 102:2097–2102
Flores JJ, Bonner WA (1974) On the asymmetric polymerization of aspartic acid enantiomers by kaolin. J Mol Evol 3:49–56
Flores JJ, Leckie JO (1973) Peptide formation mediated by cyanate. Nature 244:435–437
Fox SW, Harada K (1958) Thermal copolymerization of amino acids to a product resembling protein. Science 128:1214–1214
Fox SW, Harada K (1960) The thermal copolymerization of amino acids common to protein. J Am Chem Soc 82:3745–3751
Gibson LJ (1993) Did life begin in an RNA world? Origins 20:45–52
Harada K, Fox SW (1958) The thermal condensation of glutamic acid and glycine to linear peptides. J Am Chem Soc 80:2694–2697
Holland HD (1984) The chemical evolution of the atmosphere and oceans. Princeton University Press, Princeton
Huber C, Wächtershäuser G (1997) Activated acetic acid by carbon fixation on (Fe, Ni)S under primordial conditions. Science 276:245–247
Huber C, Wächtershäuser G (1998) Peptides by activation of amino acids with CO on (Ni, Fe)S surfaces: implications for the origin of life. Science 281:670–672
Huber C, Eisenreich W, Hecht S, Wächtershäuser G (2003) A possible primordial peptide cycle. Science 301:938–940
Imai E, Honda H, Hatori K, Brack A, Matsuno K (1999) Elongation of oligopeptides in a simulated submarine hydrothermal system. Science 283:831–833
Irving H, Williams RJP (1948) Order of stability of metal complexes. Nature 162:746–747
Isaac R, Chmielewski J (2002) Approaching exponential growth with a self-replicating peptide. J Am Chem Soc 124:6808–6809
Joyce GF (1989) RNA evolution and the origins of life. Nature 338:217–224
Joyce GF, 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 84:4398–4402
Krishnamurthy RV, Epstein S, Cronin JR, Pizzarello S, Yuen GU (1992) Isotopic and molecular analyses of hydrocarbons and monocarboxylic acids of the Murchison meteorite. Geochim Cosmochim Acta 56:4045–4058
Kvenvolden K, Lawless J, Pering K, Peterson E, Flores J, Ponnamperuma C, Kaplan IR, Moore C (1970) Evidence for extraterrestrial amino-acids and hydrocarbons in the Murchison meteorite. Nature 228:923–926
Kvenvolden KA, Lawless JG, Ponnamperuma C (1971) Nonprotein amino acids in the Murchison meteorite. Proc Natl Acad Sci USA 68:486–490
Laerdahl JK, Wesendrup R, Schwerdtfeger P (2000) D- or L-alanine: that is the question. Chemphyschem 1:60–62
Lahav N, White D, Chang S (1978) Peptide formation in the prebiotic era: thermal condensation of glycine in fluctuating clay environments. Science 201:67–69
Lanyi JK (1974) Salt-dependent properties of proteins from extremely halophilic bacteria. Bacteriol Rev 38:272–290
Larralde R, Robertson MP, Miller SL (1995) Rates of decomposition of ribose and other sugars: implications for chemical evolution. Proc Natl Acad Sci USA 92:8158–8160
Lazcano A, Miller SL (1996) The origin and early evolution of life: prebiotic chemistry, the pre-RNA world, and time. Cell 85:793–798
Lee TD, Yang CN (1956) Question of parity conservation in weak interactions. Phys Rev 104:254–258
Lee DE, Granja JR, Martinez JA, Severin K, Ghadiri MR (1996) A self-replicating peptide. Nature 382:525–528
Levine J, Augustsson T, Natarajan M (1982) The prebiological paleoatmosphere: stability and composition. Orig Life Evol Biosph 12:245–259
Levy M, Miller SL (1998) The stability of the RNA bases: implications for the origin of life. Proc Natl Acad Sci USA 95:7933–7938
Levy M, Miller SL, Oro J (1999) Production of guanine from NH4CN polymerizations. J Mol Evol 49:165–168
Li F, Fitz D, Fraser DG, Rode BM (2008) Methionine peptide formation under primordial earth conditions. J Inorg Biochem 102:1212–1217
Li F, Fitz D, Fraser DG, Rode BM (2010) Catalytic effects of histidine enationmers and glycine on the formation of dileucine and dimethionine in the salt-induced peptide formation reaction. Amino Acids 38:287–294
Limtrakul JP, Rode BM (1985) Solvent structures around sodium and chloride ions in water. Monatsh Chem 116:1377–1383
Limtrakul JP, Fujiwara S, Rode BM (1985) A quantum chemical analysis of the structural entities in aqueous sodium chloride solution and their concentration dependence. Anal Sci 1:29–32
Miller SL (1953) A production of amino acids under possible primitive earth conditions. Science 117:528–529
Miller SL (1955) Production of some organic compounds under possible primitive Earth conditions. J Am Chem Soc 77:2351–2361
Milner-White EJ, Russell MJ (2008) Predicting the conformations of peptides and proteins in early evolution. Biol Direct 3:3
Mizuno T, Weiss AH (1974) Synthesis and utilization of formose sugars. Adv Carbohydr Chem Biochem 29:173–227
Niesert U, Harnasch D, Bresch C (1981) Origin of life between Scylla and Charybdis. J Mol Evol 17:348–353
Nutman AP, McGregor VR, Friend CRL, Bennett VC, Kinny PD (1996) The Itsaq Gneiss Complex of southern West Greenland; The world’s most extensive record of early crustal evolution (3900–3600 Ma). Precambrian Res 78:1–39
Ochiai E (1978) The evolution of the environment and its influence on the evolution of life. Orig Life 9:81–91
Ochiai E (1983) Copper and the biological evolution. BioSystems 16:81–86
Ohara S, Cody GD (2010) Surface catalyzed peptide formation on sulfide minerals. Astrobiology Science Conference 2010. http://www.lpi.usra.edu/meetings/abscicon2010/pdf/5309.pdf. Accessed 30 September 2010
Oro J (1960) Synthesis of adenine from ammonium cyanide. Biochem Biophys Res Commun 2:407–412
Oro J (1961a) Comets and the formation of biochemical compounds on the primitive earth. Nature 190:389–390
Oro J (1961b) Mechanism of synthesis of adenine from hydrogen cyanide under possible primitive earth conditions. Nature 191:1193–1194
Oro J, Kimball AP (1961) Synthesis of purines under possible primitive earth conditions. I. Adenine from hydrogen cyanide. Arch Biochem Biophys 94:217–227
Oro J, Kimball AP (1962) Synthesis of purines under possible primitive earth conditions: II. Purine intermediates from hydrogen cyanide. Arch Biochem Biophys 96:293–313
Pizzarello S, Huang Y, Fuller M (2004) The carbon isotopic distribution of Murchison amino acids. Geochim Cosmochim Acta 68:4963–4969
Plankensteiner K, Righi A, Rode BM (2002) Glycine and diglycine as possible catalytic factors in the prebiotic evolution of peptides. Orig Life Evol Biosph 32:225–236
Plankensteiner K, Reiner H, Schranz B, Rode BM (2004a) Prebiotic formation of amino acids in a neutral atmosphere by electric discharge. Angew Chem Int Ed 43:1886–1888
Plankensteiner K, Righi A, Rode BM, Gargallo R, Jaumot J, Tauler R (2004b) Indications towards a stereoselectivity of the salt-induced peptide formation reaction. Inorg Chim Acta 357:649–656
Plankensteiner K, Reiner H, Rode BM (2005a) Catalytically increased prebiotic peptide formation: ditryptophan, dilysine, and diserine. Orig Life Evol Biosph 35:411–419
Plankensteiner K, Reiner H, Rode BM (2005b) Stereoselective differentiation in the salt-induced peptide formation reaction and its relevance for the origin of life. Peptides 26:535–541
Plankensteiner K, Reiner H, Rode BM (2005c) Catalytic effects of glycine on prebiotic divaline and diproline formation. Peptides 26:1109–1112
Plankensteiner K, Reiner H, Rode BM (2006) Amino acids on the rampant primordial earth: electric discharges and the hot salty ocean. Mol Divers 10:3–7
Powner MW, Gerland B, Sutherland JD (2009) Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions. Nature 459:239–242
Quigley MN, Vernon F (1996) Determination of trace metal ion concentrations in seawater. J Chem Educ 73:671–675
Reiner H, Plankensteiner K, Fitz D, Rode BM (2006) The possible influence of L-histidine on the origin of the first peptides on the primordial earth. Chem Biodivers 3:611–621
Rode BM (1999) Peptides and the origin of life. Peptides 20:773–786
Rode BM, Schwendinger MG (1990) Copper-catalyzed amino acid condensation in water – a simple possible way of prebiotic peptide formation. Orig Life Evol Biosph 20:401–410
Rode BM, Eder AH, Yongyai Y (1997) Amino acid sequence preferences of the salt-induced peptide formation reaction in comparison to archaic cell protein composition. Inorg Chim Acta 254:309–314
Rode BM, Flader W, Sotriffer C, Righi A (1999a) Are prions a relic of an early stage of peptide evolution? Peptides 20:1513–1516
Rode BM, Son HL, Suwannachot Y, Bujdak J (1999b) The combination of salt induced peptide formation reaction and clay catalysis: a way to higher peptides under primitive earth conditions. Orig Life Evol Biosph 29:273–286
Saetia S, Liedl KR, Eder AH, Rode BM (1993) Evaporation cycle experiments – a simulation of salt-induced peptide synthesis under possible prebiotic conditions. Orig Life Evol Biosph 23:167–176
Santoso S, Hwang W, Hartman H, Zhang S (2002) Self-assembly of surfactant-like peptides with variable glycine tails to form nanotubes and nanovesicles. Nano Lett 2:687–691
Sawai H, Orgel LE (1975) Prebiotic peptide-formation in the solid state. J Mol Evol 6:185–197
Sawai H, Lohrmann R, Orgel LE (1975) Prebiotic peptide-formation in the solid state. II. Reaction of glycine with adenosine 5′-triphosphate and P1, P2-diadenosine-pyrophosphate. J Mol Evol 6:165–184
Schwendinger MG, Rode BM (1989) Possible role of copper and sodium chloride in prebiotic evolution of peptides. Anal Sci 5:411–414
Schwendinger MG, Tauler R, Saetia S, Liedl KR, Kroemer RT, Rode BM (1995) Salt induced peptide formation: on the selectivity of the copper induced peptide formation under possible prebiotic conditions. Inorg Chim Acta 228:207–214
Shapiro R (1988) Prebiotic ribose synthesis: a critical analysis. Orig Life Evol Biosph 18:71–85
Shapiro R (1995) The prebiotic role of adenine: a critical analysis. Orig Life Evol Biosph 25:83–98
Sleep NH (2010) The Hadean-Archaean environment. Cold Spring Harb Perspect Biol 2:a002527
Son HL, Suwannachot Y, Bujdak J, Rode BM (1998) Salt-induced peptide formation from amino acids in the presence of clays and related catalysts. Inorg Chim Acta 272:89–94
Spitzer J, Poolman B (2009) The role of biomacromolecular crowding, ionic strength, and physicochemical gradients in the complexities of life’s emergence. Microbiol Mol Biol Rev 73:371–388
Steinman G, Cole MN (1967) Synthesis of biologically pertinent peptides under possible primordial conditions. Proc Natl Acad Sci USA 58:735–742
Steinman G, Lemmon RM, Calvin M (1964) Cyanamide: a possible key compound in chemical evolution. Proc Natl Acad Sci USA 52:27–30
Suwannachot Y, Rode BM (1998) Catalysis of dialanine formation by glycine in the salt-induced peptide formation reaction. Orig Life Evol Biosph 28:79–90
Texler NR, Holdway S, Neilson GW, Rode BM (1998) Monte Carlo simulations and neutron diffraction studies of the peptide forming system 0.5 mol kg−1 CuCl2-5 mol kg−1 NaCl-H2O at 293 and 353 K. J Chem Soc. Faraday Trans 94:59–65
Tranter GE (1985) The parity violating energy differences between the enantiomers of α-amino acids. Mol Phys 56:825–838
Vauthey S, Santoso S, Gong H, Watson N, Zhang S (2002) Molecular self-assembly of surfactant-like peptides to form nanotubes and nanovesicles. Proc Natl Acad Sci USA 99:5355–5360
Wächtershäuser G (1990) Evolution of the first metabolic cycles. Proc Natl Acad Sci USA 87:200–204
Wächtershäuser G (2000) Origin of life. Life as we don’t know it. Science 289:1307–1308
Weber LA, Caroon JM, Warden JT, Lemmon RM, Calvin M (1977) Simultaneous peptide and oligonucleotide formation in mixtures of amino acid, nucleoside triphosphate, imidazole, and magnesium ion. Biosystems 8:277–286
Wesendrup R, Laerdahl JK, Compton RN, Schwerdtfeger P (2003) Biomolecular homochirality and electroweak interactions. I. The Yamagata hypothesis. J Phys Chem A 107:6668–6673
Wilde SA, Valley JW, Peck WH, Graham CM (2001) Evidence from detrital zircons for the existence of continental crust and oceans on the Earth 4.4 Gyr ago. Nature 409:175–178
Wu CS, Ambler E, Hayward R, Hoppes D, Hudson RP (1957) Experimental test of parity conservation in beta decay. Phys Rev 105:1413–1415
Yao S, Ghosh I, Zutshi R, Chmielewski J (1998) Selective amplification by auto- and cross-catalysis in a replicating peptide system. Nature 396:447–450
Zhang S, Holmes T, Lockshin C, Rich A (1993) Spontaneous assembly of a self-complementary oligopeptide to form a stable macroscopic membrane. Proc Natl Acad Sci USA 90:3334–3338
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Fitz, D., Jakschitz, T., Rode, B.M. (2011). Salt-Induced Peptide Formation in Chemical Evolution: Building Blocks Before RNA – Potential of Peptide Splicing Reactions. In: Egel, R., Lankenau, DH., Mulkidjanian, A. (eds) Origins of Life: The Primal Self-Organization. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-21625-1_5
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