Homochirality in an early peptide world

Astrobiology

Volumn 7, Issue 5, 2007, Pages 725-732

  Brandenburg, Axel ^a,b   Lehto, Harry J ^a,c   Lehto, Kirsi M ^a,d  

^a NORDITA   (Denmark)

^b ALBANOVA UNIVERSITY CENTER   (Sweden)

^c UNIVERSITY OF TURKU   (Finland)

^d UNIVERSITY OF TURKU   (Finland)

Author keywords

Asymmetric synthesis; Autocatalysis; Prebiotic chemistry

Indexed keywords

AMINO ACID; DIPEPTIDE;

BIOGENESIS; CHEMICAL MODEL; CHEMISTRY; CONFERENCE PAPER; CONFORMATION; MOLECULAR EVOLUTION; SYNTHESIS; TIME;

AMINO ACIDS; BIOGENESIS; DIPEPTIDES; EVOLUTION, MOLECULAR; MODELS, CHEMICAL; MOLECULAR CONFORMATION; TIME FACTORS;

EID: 35548943649     PISSN: 15311074     EISSN: None     Source Type: Journal    
DOI: 10.1089/ast.2006.0093     Document Type: Conference Paper

References (24)

1. Avetisov, V.A., Goldanskii, V.I., and Kuz'min, V.V. (1991) Handedness, origin of life and evolution. Phys. Today 44, 33-41.
2. Bada, J.L. (1995) Origins of homochirality. Nature 374, 594-595.
3. Bada, J.L., Luyendyk, B.P., and Maynard, J.B. (1970) Marine sediments: dating by the racemization of amino acids. Science 170, 730-732.
4. Bartlett, P.D. and Jones, R.H. (1957) A kinetic study of the Leuchs anhydrides in aqueous solution. I. J. Am. Chem. Soc. 79, 2153-2159.
5. Blackmond, D.G. (2004) Asymmetric autocatalysis and its implications for the origin of homochirality. Proc. Natl. Acad. Sci. USA 101, 5732-5736.
6. Brandenburg, A., Andersen, A.C., Höfner, S., and Nilsson, M. (2005) Homochiral growth through enantiomeric cross-inhibition. Orig. Life Evol. Biosph. 35, 225-242.
7. Caglioti, L., Holczknecht, O., Fujii, N., Zucchi, C., and Palyi, G. (2006) Astrobiology and biological chirality, Orig. Life Evol. Biosph. 36, 459-466.
8. Cintas, P. (2002) Chirality of living systems: a helping hand from crystals and oligopeptides. Angew. Chem. Int. Ed. Engl. 41, 1139-1145.
9. Commeyras, A., Collet, H., Boiteau, L., Taillades, J., Vandenabeele-Trambouze, O., Cottet, H., Biron, J.-P., Plasson, R., Mion, L., Lagrille, O., Martin, H., Selsis, F., Dobrijevic, M. (2002) Prebiotic synthesis of sequential peptides on the Hadean beach by a molecular engine working with nitrogen oxides as energy sources. Polymer International 51, 661-665.
10. Frank, F.C. (1953) On spontaneous asymmetric synthesis. Biochim. Biophys. Acta 11, 459-464.
11. Hare, P.E. and Mitterer, R.M. (1967) Nonprotein amino acids in fossil shells. Yearbook Carnegie Institution of Washington 65, 362-364.
12. Joyce, G.F., Visser, G.M., van Boeckel, C.A.A., van Boom, J.H., Orgel, L.E., and Westrenen, J. (1984) Chiral selection in poly(C)-directed synthesis of oligo(G). Nature 310, 602-603.
13. Keszthelyi, L. (1995) Origin of the homochirality of biomolecules. Q. Rev. Biophys. 28, 473-507.
14. Kriausakul, N. and Mitterer, R.M. (1980) Comparison of isoleucine epimerization in a model dipeptide fossil protein. Geochim. Cosmochim. Acta 44, 753-757.
15. Kriausakul, N. and Mitterer, R.M. (1983) Epimerization of COOH-terminal isoleucine in fossil dipeptides. Geochim. Cosmochim. Acta 47, 963-966.
16. Lundberg, R.D. and Doty, P. (1956) Polypeptides. X. Configurarional and stereochemical effects in the amine-initiated polymerization of N-carboxy-anhydrides. J. Am. Chem. Soc. 78, 4810-4812.
17. Palyi, G., Zucchi, C., and Caglioti, L., editors. (1999) Advances in Biochirality, Elsevier, Amsterdam.
18. Palyi, G., Zucchi, C., and Caglioti L., editors. (2004) Progress in Biological Chirality, Elsevier, Oxford.
19. Plasson, R. (2003) Life: Study of the Polymerization of alpha-amino acid N-carboxyanhydrides under Prebiotic Conditions by Capillary Electrophoresis. PhD thesis, Université Montpellier II, Montpellier, France.
20. Plasson, R., Bersini, H., and Commeyras, A. (2004) Recycling Frank: spontaneous emergence of homochirality in noncatalytic systems. Proc. Natl. Acad. Sci. U.S.A. 101, 16733-16738.
21. Sandars, P.G.H. (2003) A toy model for the generation of homochirality during polymerization. Orig. Life Evol. Biosph. 33, 575-587.
22. Schwartz, A.W. (1996) Did minerals perform prebiotic combinatorial chemistry? Chem. Biol. 3, 515-518.
23. Soai, K., Shibata, T., Morioka, H., and Choji, K. (1995) Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule. Nature 378, 767-768.
24. Yu, C.-H., Newton, S.Q., Miller, D.M., Teppen, B.J., and Schäfer, L. (2001) Ab initio study of the nonequivalence of adsorption of D- and L-peptides on clay mineral surfaces. Structural Chemistry 12, 393-398.