Autopoietic self-reproduction of chiral fatty acid vesicles

Journal of the American Chemical Society

Volumn 119, Issue 2, 1997, Pages 292-301

  Morigaki, Kenichi ^a   Dallavalle, Sabrina ^b   Walde, Peter ^a   Colonna, Stefano ^b   Luisi, Pier Luigi ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLDODECANOIC ACID; FATTY ACID; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; DRUG STRUCTURE; DRUG SYNTHESIS; LIPID VESICLE; MICROSCOPY; MOLECULAR DYNAMICS; PARTICLE SIZE; THERMAL ANALYSIS;

EID: 0031047258     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961728b     Document Type: Article

References (52)

1. (a) Walde, P.; Wick, R.; Fresta, M.; Mangone, A.; Luisi, P. L. J. Am. Chem. Soc. 1994, 116, 11649-11654.
2. (b) Wick, R.; Walde, P.; Luisi, P. L. J. Am. Chem. Soc. 1995, 117, 1435-1436.
3. (c) Bachmann, P. A.; Luisi, P. L.; Lang, J. Nature 1992, 357, 57-59.
4. 1a The term self-replication is limited to linear structures whose replication is based on the template chemistry of nucleic acids; the term self-reproduction is a more general one, valid for all structures including micelles and vesicles; and the term autopoietic self-reproduction is for the particular case in which reactions leading to self-reproduction take place within the boundary of the reproductive unit (e.g., within the boundary of a vesicle).
5. 1a we use for simplicity the term fatty acid independent of the protonation degree. Therefore, a "fatty acid vesicle" is composed of a mixture of fatty acid molecules and soap molecules.
6. Maturana, H. R.; Varela, F. J. Autopoiesis and Cognition: The Realization of the Living; D. Reidel Publishing Co.: Boston, MA, 1980.
7. (a) Walde, P.; Goto, A.; Monnard, P.-A.; Wessicken, M.; Luisi, P. L. J. Am. Chem. Soc. 1994, 116, 7541-7547.
8. (b) Oberholzer, T.; Wick, R.; Luisi, P. L.; Biebricher, C. K. Biochem. Biophys. Res. Commun. 1995, 207, 250-257.
9. (c) Oberholzer, T.; Albrizio, M.; Luisi, P. L. Chem. Biol. 1995, 2, 677-682.
10. With homochiral vesicles we mean vesicles formed by one pure enantiomer; with racemic vesicles we mean vesicles composed of the racemic mixture of the two enantiomers.
11. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 83-91.
12. Evans, D. A.; Britton, T. C.; Eliman, J. A. Tetrahedron Lett. 1987, 28, 6141-6144.
13. Meyers, A. I.; Poindexter, G. S.; Brich, Z. J. Org. Chem. 1978, 43, 892-898.
14. Sonnet, P. E.; Baillangeon, M. W. Lipids 1991, 26, 295-300.
15. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
16. Archibald, S. C.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1993, 751-754.
17. Pfeffer, P. E.; Sibert, L. S.; Chirinko, J. M. J. Org. Chem. 1972, 37, 451-458.
18. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Wiley-Interscience: New York, 1980.
19. (a) Gebicki, J. M.; Hicks, M. Nature 1973, 243, 232-234.
20. (b) Gebicki, J. M.; Hicks, M. Chem. Phys. Lipids 1976, 16, 142-160.
21. (c) Hargreaves, W. R.; Deamer, D. W. Biochemistry 1978, 17, 3759-3768.
22. (a) Cistola, D. P.; Atkinson, D.; Hamilton, J. A.; Small, D. M. Biochemistry 1986, 25, 2804-2812.
23. (b) Cistola, D. P.; Hamilton, J. A.; Jackson, D.; Small, D. M. Biochemistry 1988, 27, 1881-1888.
24. (c) Cistola, D. P.; Small, D. M. J. Am. Chem. Soc. 1990, 112, 3214-3215.
25. Rosano, H. L.; Chistodoulou, A. P.; Feinstein, M. E. J. Colloid Interface Sci. 1969, 29, 335-344.
26. (a) Haines, T. H. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 160-164.
27. (b) Li, W.; Haines, T. H. Biochemistry 1986, 25, 7477-7483.
28. The cmc values for 7, 4(R), and 4(rac) are listed in Table 1. The cmc values of 4 are lower than the cmc value of the linear n-dodecanoic acid 7. This can be understood on the basis of the fact that 2-methyldodecanoic acid has a larger hydrophobic part than n-dodecanoic acid. The cmc value was the same for 4(R), 4(S), and 4(rac).
29. c is higher than room temperature. It has been generally noted that chain substitution of lipids changes their thermal properties. (Menger, F. M.; Wood, M. G., Jr.; Zhou, Q. Z.; Hopkins, H. P.; Fumero, J. J. Am. Chem. Soc. 1988, 110, 6804-6810).
30. 22b
31. (a) Talmon, Y.; Evans, D. F.; Ninham, B. W. Science 1983, 221, 1047-1048.
32. (b) Hauser, H.; Gains, N.; Müller, M. Biochemistry 1983, 22, 4775-4781.
33. (c) Kaler, E. W.; Murthy, A. K.; Rodriguez, B. E.; Zasadzinski, J. A. N. Science 1989, 245, 1371-1374.
34. (d) Safran, S. A.; Pincus, P.; Andelman, D. Science 1990, 248, 354-356.
35. (e) Cantu, L.; Corti, M.; Musolino, M.; Salina, P. Prog. Colloid Polym. Sci. 1991, 84, 21-23.
36. The carboxyl group of monomers in the aqueous phase is thought to be mostly ionized, since the solubility of protonated fatty acid in water is much lower than ionized fatty acid. For example, the solubility of n-dodecanoic acid in water is 12 μM (Bell, G. H. Chem. Phys. Lipids 1973, 10, 1-10), whereas the monomer solubility of sodium n-dodecanoate is approximately 25 mM (cmc, Table 1).
37. Similar dependence of optical activity on the protonation of carboxyl groups has been studied for amino acids and hydroxy acids. (a) Jirgensons, B. Optical Activity of Proteins and Other Macromolecules; Springer-Verlag: Berlin, 1973. (b) Katzin, L. I.; Gulyas, E. J. Am. Chem. Soc. 1968, 90, 247-251.
38. Similar dependence of optical activity on the protonation of carboxyl groups has been studied for amino acids and hydroxy acids. (a) Jirgensons, B. Optical Activity of Proteins and Other Macromolecules; Springer-Verlag: Berlin, 1973. (b) Katzin, L. I.; Gulyas, E. J. Am. Chem. Soc. 1968, 90, 247-251.
39. It is important to notice that this effect is not due to solvent perturbation effects on the chromophore, as the UV absorption spectrum in methanol (data not shown) is the same as that in water solution.
40. Colombo, L. M.; Nastruzzi, C.; Luisi, P. L.; Thomas, R. M. Chirality 1991, 3, 495-502.
41. Some giant vesicles with diameters considerably larger than 1 μm were also present after the reaction (data not shown).
42. The gradual change of the absorbance in Figure 9 is presumably due to the constraints of experimental setup. We conducted the experiment in the spectrophotometer using a round glass tube in order to make efficient mixing of the aqueous phase possible. Consequently, we could obtain only poor transmission of light through the cell. Furthermore, the rather vigorous stirring of the aqueous phase during the reaction might have caused formation of oil emulsions of 8 in the aqueous phase during the reaction, which would have influenced the turbidity.
43. Gerrand, W.; Thrush, A. M. J. Chem. Soc. 1953, 2117-2120.
44. (a) Mukerjee, P.; Mysels, K. J. Critical Micelle Concentrations of Aqueous Surfactant Systems; NSRDS-NBS, 1971.
45. (b) Campbell, A. N.; Lakshminarayana, G. R. Can. J. Chem. 1965, 43, 1729-1737.
46. (c) Harva, O. Recl. Trav. Chim. 1956, 75, 112-116.
47. (d) Markina, Z. N.; Tsikurina, N. N.; Kostova, N. Z.; Rebinder, P. A. Kolloid Zh. 1964, 26, 76-82.
48. (a) Corrin, M. L.; Klevens, H. B.; Harkins, D. J. Chem. Phys. 1946, 14, 480-486.
49. (b) Menger, F. M.; Portnoy, C. E. J. Am. Chem. Soc. 1967, 89, 4698-4703.
50. Mayer, L. D.; Hope, M. J.; Cullis, P. R. Biochim. Biophys. Acta 1986, 858, 161-168.
51. Egelhaaf, S. U.; Wehrli, E.; Müller, M.; Adrian, M.; Schurtenberger, P. J. Microsc. In press.
52. Weissmann, G.; Collins, T.; Evers, A.; Dunham, P. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 510-514.