Liposome-assisted selective polycondensation of α-amino acids and peptides

Macromolecules

Volumn 32, Issue 21, 1999, Pages 7332-7334

  Blocher, Markus ^a   Liu, Daojun ^a   Walde, Peter ^a   Luisi, Pier Luigi ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001076409     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma990917m     Document Type: Article

References (41)

1. Brack, A. Origins Life 1984, 14, 229-236.
2. Oro, J. J. Biol. Phys. 1994, 20, 135-147.
3. Fox, S. W.; Dose, K. Molecular Evolution and the Origin of Life; W. H. Freeman and Company: San Francisco, CA, 1972; pp 134-191.
4. Yanagawa, H.; Ogawa, Y.; Kojima, K.; Ito, H. Origins Life Evol. Biosphere 1987, 18, 179-207.
5. Barlett, P. D.; Jones, R. H. J. Am. Chem. Soc. 1957, 79, 2159-2197.
6. Ehler, K. W.; Orgel, L. E. Biochim. Biophys. Acta 1976,434, 233-243.
7. Ehler, K. W.; Girard, E.; Orgel, L. E. Biochim. Biophys. Acta 1977, 491, 253-264.
8. Brack, A. Origins Life Evol. Biosphere 1984, 14, 229-236.
9. Brack, A. Origins Life Evol. Biosphere 1987, 17, 367-379.
10. Hill, A. R., Jr.; Orgel, L. E. Origins Life Evol. Biosphere 1996, 26, 539-545.
11. Liu, R.; Orgel, L. E. Origins Life Evol. Biosphere 1998,28, 47-60.
12. Taillades, J.; Beuzelin, I.; Garrel, L.; Tabacik, V.; Bied, C.; Commeyras, A. Origins Life Evol. Biosphere 1996,28, 6177.
13. Huber, C.; Wächtershäuser, G. Science 1998, 281, 66-68.
14. Ferris, J. P.; Hill, A. R., Jr.; Liu, R.; Orgel, L. E. Nature 1996, 381, 59-61.
15. Liu, R.; Orgel, L. E. Origins Life Evol. Biosphere 1998, 28, 245-257.
16. Hill, A. R., Jr.; Böhler, C.; Orgel, L. E. Origins Life Evol. Biosphere 1998, 28, 47-60.
17. Böhler, C.; Hill, A. R., Jr.; Orgel, L. E. Origins Life Evol. Biosphere 1996, 26, 1-5.
18. Fukada, K.; Shibasaki, Y.; Nakahara, H. J. Macromol. Sei.Chem. 1981, 5, 999-1014.
19. Kunieda, N.; Watanabe, M.; Okamoto, K.; Kinoshita, M. Makromol. Chem. 1981, 182, 211-214.
20. Folda, T.; Gros, L.; Ringsdorf, H. Makromol. Chem. Rapid Commun. 1982, 3,167-174.
21. Laschewsky, A.; Ringsdorf, H.; Schmidt, G.; Schneider, J. J. Am. Chem. Soc. 1987, 709, 788-796.
22. Neumann, R.; Ringsdorf, H.; Patton, E. V.; O'Brien, D. F. Biochim. Biophys. Acta 1987, 898, 338-348.
23. Shibata, A.; Yamashita, S.; Ito, Y.; Yamashita, T. Biochim. Biophys. Acta 1986, 854, 147-150.
24. Shibata, A.; Yamashita, S.; Ueno, S.; Yamashita, T. Bull. Chem. Soc. Jpn. 1989, 62, 257-261.
25. Nishikawa, N.; Arai, M.; Ono, M.; Itoh, I. Chem. Lett. 1993, 2017-2020.
26. Nishikawa, N.; Miyasaka, T.; Ono, M.; Itho, I. J. Synth. Org. Chem. Jpn. 1995, 53, 275-283.
27. Li, Z.-C.; He, W.; Li, F.-M. React. Fund. Polym. 1996, 30, 299-308.
28. Loomis, F. W. Four Billion Years; Sinauer Associates, Inc.: Massachusetts, 1988.
29. Morowitz, H. J. Beginnings of Cellular Life; Yale University Press: London, 1992.
30. Ourisson, G.; Nakatani, Y. C. R. Acad. Sei. Paris, lib 1996, 332,323-334. Ourisson, G.; Nakatani, Y. Tetrahedron 1999, 55, 3183-3190.
31. Orô, J.; Lazcano, A. In Prebiological Self-Organization of Matter; Ponnamperuma, C., Eirich, F. R., Eds.; Deepak Publishing: Hampton, VA, 1990.
32. Bachmann, P. A.; Luisi, P. L.; Lang, J. Nature 1992, 357, 57-59.
33. Walde, P.; Goto, A.; Monnard, P.-A.; Wessicken, M.; Luisi, P. L. J. Am. Chem. Soc. 1994, 116, 7541-7547.
34. Walde, P.; Wick, R.; Fresta, M.; Mangone, A.; Luisi, P. L. J. Am. Chem. Soc. 1994, 116, 11649-11654.
35. Belleau, B.; Malek, G. J. Am. Chem. Soc. 1968, 90, 16511652.
36. H-Trp-OH in a 0.4 M imidazole buffer pH 6.80 was incubated with a 2.5-fold excess of carbonyldiimidazole (GDI) at 0 C for 2 min. Yields up to 95% of NCA-Trp-OH and N-[imidazolyl-(l)-carbonyl]tryptophan were obtained, as documented also for other amino acids.6'7'10'11-14"17 This resulting NCA-Trp-OH solution was mixed 1:1 with an aqueous suspension of "100 nm liposomes" (50 mM POPC) in a 0.4 M imidazole buffer pH 6.80 prepared by the extrusion technique, using for final extrusions polycarbonate membranes with 100 nm pore diameter.37 Then it 'was incubated on a shaker (VORTEX-Genie 2, Scientific Industries) for 12 h at room temperature.
37. Mayer, L. D.; Hope, M. J.; Cullis, P. R. Biochim. Biophys. Acta 1986, 858, 161-168.
38. White, S. H.; Wimley, W. C. Biochim. Biophys. Acta 1998, 1376, 339-352.
39. Yau, W.-M.; Wimley, W. C.; Gawrisch, K.; White, S. H. Biochemistry 1998, 37, 14713-14718.
40. After 26 h incubation of 10 mM H-Trp2-OH, 2 mM EEDQ in 50 mM phosphate buffer, 1.2% v/v ACN, pH 5.90, at room temperature in the presence of "100 nm liposomes" (25 mM POPC) or reference (without liposomes), 25 fiL of the reaction mixture was analyzed by HPLC (HP1100 LC, buffers as above, starting with 30% up to 95% B, gradient: 1.625% B/min, 1 mL/min) using a C18 column (MachereyNagel, ET 250/4 Nucleosil 100-5) and a diode array detector (HP1100 DAD) in series with a single quadrupole mass spectrometry detector (HP1100 MSD). Quantification has been performed using absorbance at 280 nm.
41. Haugland, R. P. Handbook of Fluorescent Probes and Research Chemicals, 6th ed.; Molecular Probes: Leiden, The Netherlands, 1996; pp 72-73.