Abstract
The salt-induced peptide formation (SIPF) reaction takes place readily under mild reaction conditions and proceeds via a copper complex. Its ease of reaction and the universality for prebiotic scenarios add weights to the arguments in favour of the importance of peptide and proteins in the tug of war with the RNA world hypothesis. In addition, the SIPF reaction has a preference for l-form amino acids in dipeptide formation, casting light on the puzzle of biohomochirality, especially for the amino acids with aliphatic side chains. A detailed investigation on the behaviour of aliphatic leucine in the SIPF reaction is presented in this paper, including the catalytic effects of glycine, l- and d-histidine as well as the stereoselectivity under all the reaction conditions above. The results show a relatively low reactivity and stereoselectivity of leucine in the SIPF reaction, while both glycine and histidine enantiomers remarkably increase the yields of dileucine by factors up to 40. Moreover, a comparative study of the effectiveness of l- and d-histidine in catalysing the formation of dimethionine was also carried out and extends the scope of mutual catalysis by amino acid enantiomers in the SIPF reaction.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Barron LD (1994) CP violation and molecular physics. Chem Phys Lett 221:311–316. doi:10.1016/0009-2614(94)00253-3
Berger R, Quack M (2000) Electroweak quantum chemistry of alanine: parity violation in gas and condensed phases. Chem Phys Chem 1:57–60. doi:10.1002/1439-7641(20000804)1:1<57::AID-CPHC57>3.0.CO;2-J
Carver J (1981) Prebiotic atmospheric oxygen levels. Nature 292:136–138. doi:10.1038/292136a0
Fitz D, Reiner H, Plankensteiner K et al (2007) Possible origins of biohomochirality. Curr Chem Biol 1:41–52. doi:10.2174/187231307779813995
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. doi:10.1016/j.jinorgbio.2008.07.010
Fox SW, Harada K (1960) The thermal copolymerization of amino acids common to protein. J Am Chem Soc 82:3745–3751. doi:10.1021/ja01499a069
Hofmann HJ, Grey K, Hickman AH et al (1999) Origin of 3.45 Ga coniform stromatolites in Warrawoona Group, Western Australia. Geol Soc Am Bull 111:1256–1262. doi:10.1130/0016-7606(1999)111<1256:OOGCSI>2.3.CO;2
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. doi:10.1126/science.281.5377.670
Imai E, Honda D, Hatori K, Brack A et al (1999) Elongation of oligopeptides in a simulated submarine hydrothermal system. Science 283:831–833. doi:10.1126/science.283.5403.831
Laerdahl JK, Wesendrup R, Schwerdtfeger P (2000) d- or l-alanine: that is the question. Chem Phys Chem 1:60–62. doi:10.1002/1439-7641(20000804)1:1<60::AID-CPHC60>3.0.CO;2-M
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. doi:10.1126/science.663639
Lambert JF (2008) Adsorption and polymerization of amino acids on mineral surfaces: a review. Orig Life Evol Biosph 38:211–242. doi:10.1007/s11084-008-9128-3
Lee TD, Yang CN (1956) Question of parity conservation in weak interactions. Phys Rev 104:254–258. doi:10.1103/PhysRev.104.254
Leman L, Orgel L, Chadiri MR (2004) Carbonyl sulfide-mediated prebiotic formation of peptides. Science 306:283–286. doi:10.1126/science.1102722
Levine JS, Augustsson TR, Natarajan M (1982) The prebiological paleoatmosphere: stability and composition. Orig Life 12:245–259. doi:10.1007/BF00926894
Li F, Fitz D, Fraser DG et al (2008) Methionine peptide formation under primordial earth conditions. J Inorg Biochem 102:1212–1217. doi:10.1016/j.jinorgbio.2007.12.020
Liedl KR, Rode BM (1992) Ab initio calculations concerning the reaction mechanism of the copper(II) catalyzed glycine condensation in aqueous sodium chloride solution. Chem Phys Lett 197:181–186. doi:10.1016/0009-2614(92)86044-I
Limtrakul JP, Rode BM (1985) Solvent structures around Na+ and Cl− ions in water. Monatsh Chem 116:1377–1383. doi:10.1007/BF00810478
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. doi:10.2116/analsci.1.29
Mason SF, Tranter GE (1983) Energy inequivalence of peptide enantiomers from parity non-conservation. J Chem Soc Chem Commun 117–119. doi:10.1039/c39830000117
Mason SF, Tranter GE (1984) The parity-violating energy difference between enantiomeric molecules. Mol Phys 53:1091–1111. doi:10.1080/00268978400102881
Miller SL (1953) A production of amino acids under possible primitive earth conditions. Science 117:528–529. doi:10.1126/science.117.3046.528
Nutman AP, McGregor VR, Friend CRL et al (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. doi:10.1016/0301-9268(95)00066-6
Ochiai E (1978) Evolution of the environment and its influence on the evolution of life. Orig Life 9:81–91. doi:10.1007/BF00931406
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. doi:10.1023/A:1016523207700
Plankensteiner K, Reiner H, Schranz B et al (2004a) Prebiotic formation of amino acids in a neutral atmosphere by electric discharge. Angew Chem Int Ed 43:1886–1888. doi:10.1002/anie.200353135
Plankensteiner K, Righi A, Rode BM et al (2004b) Indications towards a stereoselectivity of the salt-induced peptide formation reaction. Inorg Chim Acta 357:649–656. doi:10.1016/j.ica.2003.06.012
Plankensteiner K, Reiner H, Rode BM (2005a) Catalytic effects of glycine on prebiotic divaline and diproline formation. Peptides 26:1109–1112. doi:10.1016/j.peptides.2005.01.007
Plankensteiner K, Reiner H, Rode BM (2005b) Catalytically increased prebiotic peptide formation: ditryptophan, dilysine, and diserine. Orig Life Evol Biosph 35:411–419. doi:10.1007/s11084-005-1971-x
Plankensteiner K, Reiner H, Rode BM (2005c) Stereoselective differentiation in the salt-induced peptide formation reaction and its relevance for the origin of life. Peptides 26:535–541. doi:10.1016/j.peptides.2004.11.019
Ponnamperuma C, Peterson E (1965) Peptide synthesis from amino acids in aqueous solution. Science 147:1572–1574. doi:10.1126/science.147.3665.1572
Rabinovitz J (1971) Note on the role of cyanides and polyphosphates in the formation of peptides in aqueous solutions of amino acids, at room temperature, as a possible prebiotic process. Helv Chim Acta 54:1483–1485. doi:10.1002/hlca.19710540532
Reiner H, Plankensteiner K, Fitz D, Rode BM (2006) The possible influence of l-histidine on the origin of first peptides on the primordial earth. Chem Biodivers 3:611–621. doi:10.1002/cbdv.200690064
Rode BM (1999) Peptides and the origin of life. Peptides 20:773–786. doi:10.1016/S0196-9781(99)00062-5
Rubbia C (1985) Experimental observation of the intermediate vector bosons W +, W −, and Z 0. Rev Mod Phys 57:699–722. doi:10.1103/RevModPhys.57.699
Schwendinger MG, Rode BM (1989a) Possible role of copper and sodium chloride in prebiotic evolution of peptides. Anal Sci 5:411–414. doi:10.2116/analsci.5.411
Schwendinger MG, Rode BM (1989b) A Monte Carlo simulation of a supersaturated sodium chloride solution. Chem Phys Lett 155:527–532. doi:10.1016/0009-2614(89)87467-6
Schwendinger MG, Tauler R, Saetia S et al (1995) Salt induced peptide formation: on the selectivity of the copper induced peptide formation under possible prebiotic conditions. Inorg Chim Acta 228:207–214. doi:10.1016/0020-1693(94)04186-Y
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. doi:10.1023/A:1006503928834
Suwannachot Y, Rode BM (1999) Mutual amino acid catalysis in salt-induced peptide formation supports this mechanism’s role in prebiotic peptide evolution. Orig Life Evol Biosph 29:463–471. doi:10.1023/A:1006583311808
Tranter GE (1985) The parity violating energy differences between the enantiomers of agr-amino acids. Mol Phys 56:825–838. doi:10.1080/00268978500102741
Weinberg S (1980) Conceptual foundations of the unified theory of weak and electromagnetic interactions. Rev Mod Phys 52:515–523. doi:10.1103/RevModPhys.52.515
Wu CS, Ambler E, Hayward RW et al (1957) Experimental test of parity conservation in beta decay. Phys Rev 105:1413–1415. doi:10.1103/PhysRev.105.1413
Yanagawa H, Nishizawa M, Kojima K (1984) A possible prebiotic peptide formation from glycinamide and related compounds. Orig Life 14:267–272. doi:10.1007/BF00933667
Acknowledgments
This work was financially supported by the Austrian Ministry of Education, Science and Culture (BMWF, Grant No. 45.530/0003-11/6a/2007) and by the Austrian Science Foundation (Fonds zur Förderung der wissenschaftlichen Forschung, Projekt P19334-N17). The support offered to Feng Li by the Overseas Research Students Awards Scheme (United Kingdom), the Scatcherd European Scholarship (University of Oxford) and the Hester Cordelia Parsons Fund (University of Oxford) are also gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Li, F., Fitz, D., Fraser, D.G. et al. Catalytic effects of histidine enantiomers and glycine on the formation of dileucine and dimethionine in the salt-induced peptide formation reaction. Amino Acids 38, 287–294 (2010). https://doi.org/10.1007/s00726-009-0249-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00726-009-0249-4