Helical pores self-assembled from homochiral dendritic dipeptides based on L-Tyr and nonpolar α-amino acids

Journal of the American Chemical Society

Volumn 129, Issue 18, 2007, Pages 5992-6002

  Percec, Virgil ^a   Dulcey, Andrés E ^a   Peterca, Mihai ^a   Adelman, Peter ^a   Samant, Ritika ^a   Balagurusamy, Venkatachalapathy S K ^a   Heiney, Paul A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CRYSTAL STRUCTURE; MOLAR MASS; POROUS MATERIALS; SELF ASSEMBLY; SUBSTITUTION REACTIONS;

HELICAL POROUS COLUMNS; HOMOCHIRAL DENDRITIC DIPEPTIDES; PERIODIC ARRAYS; RETROSTRUCTURAL ANALYSIS;

PEPTIDES;

ALPHA AMINO ACID; DIPEPTIDE;

ARTICLE; CHANNEL GATING; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; PEPTIDE SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY; X RAY DIFFRACTION;

AMINO ACIDS; CALORIMETRY, DIFFERENTIAL SCANNING; DIPEPTIDES; PROTEIN CONFORMATION; SPECTRUM ANALYSIS; TYROSINE; X-RAY DIFFRACTION;

EID: 34248578788     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071088k     Document Type: Article

References (61)

1. (a) Klug, A. Angew. Chem., Int. Ed. Engl. 1983, 22, 565-582.
2. (b) Klug, A. Philos. Trans. R. Soc. London, Ser. B 1999, 354, 531-535.
3. (a) MacKinnon, R. Angew. Chem., Int. Ed. 2004, 43, 4265-4277.
4. (b) Agre, P. Angew. Chem., Int. Ed. 2004, 43, 4278-4290.
5. Wallace, B. A. Biophys. J. 1986, 49, 295-306.
6. (a) Zasloff, M. Nature 2002, 415, 389-395.
7. (b) White, S. H.; Winley, W. C.; Selsted, M. E. Curr. Opin. Struct. Biol. 1995, 5, 521-527.
8. (a) Gouaux, E. J. Struct. Biol. 1998, 121, 110-122.
9. (b) Gouaux, E. Curr. Opin. Struct. Biol. 1997, 7, 566-573.
10. Bayley, H.; Cremer, P. S. Nature 2001, 413, 226-230.
11. (a) Ishii, D.; Kinbara, K.; Ishida, Y.; Ishii, N.; Okochi, M.; Yohda, M.; Aida, T. Nature 2003, 423, 628-632.
12. (b) Douglas, T.; Young, M. Science 2006, 312, 873-875.
13. (a) Nolte, R. J. M.; van Beijnen, A. J. M.; Neevel, J. G.; Zwikker, J. W.; Verkley, A. J.; Drenth, W. Isr. J. Chem. 1984, 24, 297-301.
14. (b) Jullien, L.; Lehn, J.-M. Tetrahedron Lett. 1988, 29, 3803-3806.
15. (c) Cross, G. G.; Fyles, T. M.; James, T. D.; Zojaji, M. Synlett 1993, 7, 449-460.
16. (d) Gokel, G. W.; Ferdani, R.; Liu, J.; Pajewski, R.; Shabany, H.; Uetrecht, P. Chem. - Eur. J. 2001, 7, 33-39.
17. (e) Bong, D. T.; Clark, T. D.; Granja, J. R.; Ghadiri, M. R. Angew. Chem., Int. Ed. 2001, 40, 988-1011.
18. (f) Sakai, N.; Mareda, J.; Matile, S. Acc. Chem. Res. 2005, 38, 79-87.
19. (g) Rosselli, S.; Ramminger, A.-D.; Wagner, T.; Silier, B.; Wiegand, S.; Haussler, W.; Lieser, G.; Scheumann, V.; Hoger, S. Angew. Chem., Int. Ed. 2001, 40, 3138-3141.
20. (h) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001. 101, 3893-4012.
21. (i) Fenniri, H.; Deng, B.-L.; Ribbe, A. E. J. Am. Chem. Soc. 2002, 124, 11064-11072.
22. (j) Hecht, S.; Khan, A. Angew. Chem., Int. Ed. 2003, 42, 6021-6024.
23. (k) Couet, J.; Jeyaprakash, J. D.; Samuel, S.; Kopyshev, A.; Santer, S.; Biesalski, M. Angew. Chem., Int. Ed. 2005, 44, 3297-3301.
24. (a) Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Nature 1993, 366, 324-327.
25. (b) Petitjean, A.; Cuccia, L. A.; Lehn, J.-M.; Nierengarten, H.; Schmutz, M. Angew. Chem., Int. Ed. 2002, 41, 1195-1198.
26. (c) Ohkita, M.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. - Eur. J. 1999, 5, 3471-3481.
27. (d) Schmitt, J.-L.; Stadler, A.-M.; Kyritsakas, N.; Lehn, J.-M. Helv. Chim. Acta 2003, 86, 1598-1624.
28. (e) Schmitt, J.-L.; Lehn, J.-M. Helv. Chim. Acta 2003, 86, 3417-3426.
29. (a) Percec, V.; Dulcey, A. E.; Balagurusamy, V. S. K.; Miura, Y.; Smidrkal, J.; Peterca, M.; Nummelin, S.; Edlund, U.; Hudson, S. D.; Heiney, P. A.; Duan, H.; Magonov, S. N.; Vinogradov, S. A. Nature 2004, 430, 764-768.
30. (b) Rouhi, M. Chem. Eng. News 2004, 82 (33). 4.
31. (c) Borman, S. Chem. Eng. News 2004, 82 (51), 53-61.
32. (a) Percec, V.; Dulcey, A. E.; Peterca, M.; Hies, M.; Ladislaw, J.; Rosen, B. M.; Edlund, U.; Heiney, P. A. Angew. Chem., Int. Ed. 2005, 44, 6516-6521.
33. (b) Percec, V.; Dulcey, A. E.; Peterca, M.; Hies, M.; Sienkowska, M. J.; Heiney, P. A. J. Am. Chem. Soc. 2005, 127, 17902-17909.
34. (c) Percec, V.; Dulcey, A. E.; Peterca, M.; Hies, M.; Nummelin, S.; Sienkowska, M. J.; Heiney, P. A. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 2518-2523.
35. (d) Percec, V.; Dulcey, A. E.; Peterca, M.; Ilies, M.; Miura, Y.; Edlund, U.; Heiney, P. A. Aust. J. Chem. 2005, 58, 472-482.
36. (e) Peterca, M.; Percec, V.; Dulcey, A. E.; Nummelin, S.; Korey, S.; Hies, M.; Heiney, P. A. J. Am. Chem. Soc. 2006, 128, 6713-6720.
37. (a) Monod, J.; Changeux, J.-P.; Jacob, F. J. Mol. Biol. 1963, 6, 306-329.
38. (b) Perutz, M. Mechanisms of Cooperativity and Allosteric Regulation in Proteins; Cambridge University Press: Cambridge, U.K., 1990.
39. (c) Evans, P. R. Curr. Opin. Struct. Biol. 1991, 1, 773-779.
40. Kronin, J. S.; Ginah, F. O.; Murray, A. R.; Copp, J. D. Synth. Commun. 1996, 26, 3491-3494.
41. Mitsunobu, O. Synthesis 1981, 1-28.
42. (a) Percec, V.; Cho, W.-D.; Ungar, G.; Yeardley, D. J. P. J. Am. Chem. Soc. 2001, 123, 1302-1315.
43. (b) Percec, V.; Mitchell, C. M.; Cho, W.-D.; Uchida, S.; Glodde, M.; Ungar, G.; Zeng, X.; Liu, Y.; Balagurusamy, V. S. K.; Heiney, P. A. J. Am. Chem. Soc. 2004, 126, 6078-6094.
44. (a) Kwon, Y. K.; Chvalun, S.; Schneider, A.-I.; Blackwell, J.; Percec, V.; Heck, J. A. Macromolecules 1994, 27, 6129-6132.
45. (b) Kwon, Y. K.; Chvalun, S. N.; Blackwell, J.; Percec, V.; Heck, J. A. Macromolecules 1995, 28, 1552-1558.
46. (c) Percec, V.; Glodde, M.; Bera, T. K.; Miura, Y.; Shiyanovskaya, I.; Singer, K. D.; Balagurusamy, V. S. K.; Heiney, P. A.; Schnell, I.; Rapp, A.; Spiess, H.-W.; Hudson, S. D.; Duan, H. Nature 2002, 419, 384-387.
47. (d) Percec, V.; Glodde, M.; Peterca, M.; Rapp, A.; Schnell, I.; Spiess, H. W.; Bera, T. K.; Miura, Y.; Balagurusamy, V. S. K.; Aqad, E.; Heiney, P. A. Chem. - Eur. J. 2006, 12, 6298-6314.
48. (e) Percec, V.; Peterca, M.; Sienkowska, M. J.; Hies, M. A.; Aqad, E.; Smidrkal, J.; Heiney, P. A. J. Am. Chem. Soc. 2006, 128, 3324-3334.
49. (a) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4012.
50. (b) Brunsveld, L.; Zhang, H.; Glasbeek, M.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 6175-6182.
51. (c) Percec, V.; Rudick, J. G.; Peterca, M.; Wagner, M.; Obata, M.; Mitchell, C. M.; Cho, W.-D.; Balagurusamy, V. S. K.; Heiney, P. A. J. Am. Chem. Soc. 2005, 127, 15257-15264.
52. (d) Jin, W. I.; Fukushima, T.; Niki, M.; Kosaka, A. I.; Ishii, N. I.; Aida, T. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 10801-10806.
53. (a) Green, M. M.; Park, J.-W.; Sato, T. I.; Teramoto, A. I.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3139-3154.
54. (b) Jonkheijm, P.; van der Schoot, P.; Schenning, A. P. H. J.; Meijer, E. W. Science 2006, 313, 80-83.
55. (c) Percec, V.; Ungar, G.; Peterca, M. Science 2006, 313, 55-56.
56. (a) Percec, V.; Ahn, C.-H.; Ungar, G.; Yeardley, D. J. P.; Möller, M.; Sheiko, S. S. Nature 1998, 391, 161-164.
57. (b) Percec, V.; Ahn, C.-H.; Cho, W.-D.; Jamieson, A. M.; Kim, J.; Leman, T.; Schmidt, M.; Gerle, M.; Möller, M.; Prokhorova, S. A.; Sheiko, S. S.; Cheng, S. Z. D.; Zhang, A.; Ungar, G.; Yeardley, D. J. P. J. Am. Chem. Soc. 1998, 120, 8619-8613.
58. (a) Emrick, T.; Fréchet, J. M. J. Curr. Opin. Colloid Interface Sci. 1999, 4, 15-23.
59. (b) Tomalia, D. A. Mater. Today 2005, 8, 34-46.
60. (c) Hecht, S. Mater. Today 2005, 8, 48-55.
61. (d) Lehn, J.-M. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4763-4768.