Separation of enantiomers and racemate formation in two-dimensional crystals at the water surface from racemic α-amino acid amphiphiles: Design and structure

Journal of the American Chemical Society

Volumn 119, Issue 5, 1997, Pages 933-942

  Weissbuch, Isabelle ^a   Berfeld, Maria ^a   Bouwman, Wim ^b   Kjaer, Kristian ^b   Als Nielsen, Jens ^c   Lahav, Meir ^a   Leiserowitz, Leslie ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID ANALYSIS; ARTICLE; CRYSTALLIZATION; DRUG PURIFICATION; ENANTIOMER; TECHNIQUE;

EID: 0031025230     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9613926     Document Type: Article

References (52)

1. Pasteur, L. Ann. Phys. 1848, 24, 442.
2. Havinga, E. Biochem. Biophys. Acta 1954, 13, 171.
3. Wald, G. N. Y. Acad. Sci. 1957, 69, 352.
4. Addadi, L.; Lahav, M. In Origins of Optical Activity in Nature; Walker, D. C., Ed.; Elsevier: New York, 1979; p 179.
5. Weissbuch, I.; Addadi, L.; Berkovitch-Yellin, Z.; Gati, E.; Lahav, M.; Leiserowitz, L. Nature 1984, 310, 161.
6. Weissbuch, I.; Popovitz-Biro, R.; Leiserowitz, L.; Lahav, M. In The Lock and-Key Principle; Behr, J. P., Ed.; John Wiley & Sons Ltd.: 1994; p 173.
7. Rose, P. L.; Harvey, N. G.; Arnett, E. M. In Advances in Physical Organic Chemistry; Academic Press Limited: 1993; Vol. 28, p 45.
8. Lösche, M.; Sackmann, E.; Möhwald, H. Ber. Bunsenges. Phys. Chem. 1983, 87, 848.
9. Weiss, R. M.; McConnell, H. M. Nature 1984, 310, 47.
10. Rietz, R.; Brezesinski, G.; Möhwald, H. Ber. Bunsenges. Phys. Chem. 1993, 97, 1394.
11. Brezesinski, G.; Rietz, R.; Kjaer, K.; Bouwman, W. G.; Möhwald, H. Nuovo Cimento D 1994, 16, 1487.
12. Scalas, E.; Brezesinski, G.; Bouwman, W. G.; Kjaer, K.; Möhwald, H. Proc. XXX the Rencontres de Moriond 1995, 165.
13. Scalas, E.; Brezesinski, G.; Möhwald, H.; Kaganer, V. M.; Bouwman, W. G.; Kjaer, K., Thin Solid Films; 1996, Proceedings of the LB7 Conference, Ancona, 1996, 284/285, 56.
14. Scalas, E.; Brezesinski, G.; Möhwald, H.; Kaganer, V. M.; Bouwman, W. G.; Kjaer, K., Thin Solid Films; 1996, Proceedings of the LB7 Conference, Ancona, 1996, 284/285, 56.
15. Rietz, R.; Rettig, W.; Brezesinski, G.; Bouwman, W. G.; Kjaer, K.; Möhwald, H., Thin Solid Films; 1996, Proceedings of the LB7 Conference, Ancona, 1996, 284/285, 211.
16. Rietz, R.; Rettig, W.; Brezesinski, G.; Bouwman, W. G.; Kjaer, K.; Möhwald, H., Thin Solid Films; 1996, Proceedings of the LB7 Conference, Ancona, 1996, 284/285, 211.
17. Gehlert, U.; Weidemann, G.; Volhardt, D.; Bringezu, F.; Struth, B.; Scalas, E.; Brezesinski, G.; Möhwald, H. HASYLAB, DESY, Annual Report; 1994; p 421.
18. Nassoy, P.; Goldmann, M.; Bouloussa, O.; Rondelez, F. Phys. Rev. Lett. 1995, 75, 457.
19. Echardt, C. J.; Peachey, N. M.; Swanson, D. R.; Takacs, J. M.; Khan, M. A.; Gong, X.; Kim, J.-H.; Wang, J.; Uphaus, R. A. Nature 1993, 362, 614.
20. Stevens, F.; Dyer, D. J.; Walba, D. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 900.
21. Weissbuch, I.; Addadi, L.; Lahav, M.; Leiserowitz, L. J. Am. Chem. Soc. 1988, 110, 561-567.
22. Torii, K.; Iitaka, Y. Acta Crystallogr. 1970, B26, 1317.
23. Torii, K.; Iitaka, Y. Acta Crystallogr. 1971, B27, 2237.
24. Torii, K.; Iitaka, Y. Acta Crystallogr. 1973, B29, 2799.
25. Harding, M. M.; Howieson, R. M. Acta Crystallogr. 1976, B32, 2799.
26. In systems with two independent molecules per asymmetric unit the molecules are related by pseudo-translation.
27. Legros, J.-P.; Kvick, Å. Acta Crystallogr. 1980, B36, 3052-3059.
28. Weissbuch, I.; Frolow, F.; Addadi, L.; Lahav, M.; Leiserowitz, L. J. Am. Chem. Soc. 1990, 112, 7718.
29. Mallikarjunan, M.; Rao, S. T. Acta Crystallogr. 1969, B25, 296.
30. Benedetti, E.; Pedone, C.; Sirigu, A. Acta Crystallogr. 1973, B29 730.
31. diBlasio, B.; Pedone, C.; Sirigu, A. Acta Crystallogr. 1975, B31, 601.
32. Nakata, K.; Y. Takaki; Sakurai; K., Acta Crystallogr. 1980, B36, 504.
33. Mathieson, A. M. Acta Crystallogr. 1952, 5, 332.
34. Mathieson, A. M. Acta Crystallogr. 1953, 6, 399.
35. 36-38 led to the present reexamination of such types of α-amino acid molecules.
36. Wolf, S. G.; Leiserowitz, L.; Lahav, M.; Deutsch, M.; Kjaer, K.; Als-Nielsen, J. Nature 1987, 328, 63.
37. Jacquemain, D.; Grayer Wolf, S.; Leveiller, F.; Deutsch, M.; Kjaer, K.; Als-Nielsen, J.; Lahav, M.; Leiserowitz, L. Angew. Chem., Int. Ed. Engl. 1992, 31, 130.
38. Als-Nielsen, J.; Jacquemain, D.; Kjaer, K.; Leveiller, F.; Lahav, M.; Leiserowitz, L. Physics Reports 1994, 246, 251.
39. Als-Nielsen, J.; Kjaer, K.; Linderholm, J.; Bang, S.; Skaarup, P.; Vogeley, E.; Hansen, E. In Annual Progress Report of the Department of Solid State Physics 1991; Als-Nielsen, J., Skov Pedersen, J., Lebech, B., Eds.; Risø National Laboratory: Roskilde, Denmark, 1992; p 10.
40. Kjaer, K.; Majewski, J.; Schulte-Schrepping, H.; Weigelt, J. In Annual Progress Report of the Department of Solid State Physics 1992; Skov Pedersen, J., Lebech, B., Lindgaard, P.-A., Eds.; Risø National Laboratory: Roskilde, Denmark, 1993; p 131.
41. Bernstein, J.; Etter, M. C.; Leiserowitz, L. In Structure Correlation; Bürgi, H. B., Dunitz, H. D., Eds.; VCH: Weinheim, 1994; Vol. 2, p 431.
42. Landau, E. M.; Grayer Wolf, S.; Levanon, M.; Leiserowitz, L.; Lahav, M.; Sagiv, J. J. Am. Chem. Soc. 1989, 111, 1436.
43. Leveiller, F.; Jacquemain, D.; Leiserowitz, L.; Kjaer, K.; Als-Nielsen, J. J. Phys. Chem. 1992, 96, 10380.
44. Weissbuch, I.; Addadi, L.; Berkovitch-Yellin, Z.; Gati, E.; Weinstein, S.; Lahav, M.; Leiserowitz, L. J. Am. Chem. Soc. 1983, 105, 6613.
45. hk. (See: Kjaer, K. Physica B 1994, 198, 100).
46. The film thickness w(Å) ≃ 0.9*2π/FWHM, the Scherrer formula.
47. These split peaks indicate the presence of two to three different yet similar phases, arising presumably from small differences in molecular conformation.
48. n-AA.
49. 2, Molecular Modeling Software for materials research produced by BIOSYM/Molecular Simulations Inc., San Diego, CA and Cambridge, UK.
50. -1, yields a layer "repeat" distance of ∼20 Å and so a maximum number of three layers (the molecular length is ∼23 Å).
51. 50
52. Kjaer, K.; Bouwman, W. G. In Annual Progress Report of the Department of Solid State Physics 1994; Lindgaard, P.-A., Bechgaard, K., Clausen, K. N., Feidenhans'l, R., Eds.; Risø National Laboratory: Roskilde, Denmark, 1995; p 79.