TFE solution of the crown peptide nanostructures (5–40 mM)
was added. Then, after 400 s, a 10% Triton X-100 solution was
added and the experiment was terminated after 500 s.
7 Y. R. Vandenburg, B. D. Smith, E. Biron and N. Voyer, Chem.
Commun., 2002, 16, 1694–1695.
8 N. Voyer and M. Robitaille, J. Am. Chem. Soc., 1995, 117, 6599–6600.
9 J.-C. Meillon and N. Voyer, Angew. Chem., Int. Ed. Engl., 1997, 36,
967–969.
10 N. Voyer, L. Potvin and E. Rousseau, J. Chem. Soc., Perkin Trans. 2,
Acknowledgements
1997, 1469–1471.
11 E. Biron, N. Voyer, J.-C. Meillon, M.-E. Cormier and M. Auger,
Biopolymers, 2000, 55, 364–372.
12 E. Biron, F. Otis, J. C. Meillon, M. Robitaille, J. Lamothe, P. Van Hove,
M. C. Cormier and N. Voyer, Bioorg. Med. Chem., 2004, 6, 1279–
1290.
This work was supported by the NSERC of Canada, the FQRNT
of Quebec, and the Universite´ Laval. Pierre-Luc Boudreault
thanks the NSERC and FQRNT for postgraduate scholarships
and Marc-Andre´ Laliberte´ for illustrations.
13 M. Ouellet, F. Otis, N. Voyer and M. Auger, Biochim. Biophys. Acta,
2006, 1758, 1235–1244.
14 For other works involving crown ethers and crown modified peptides
see: G. W. Gokel, W. M. Leevy and M. E. Weber, Chem. Rev., 2004,
104, 2723–2750; J.-P. Mazaleyrat, Y. Goubard, M.-V. Azzani, M.
Wakselman, C. Peggion, F. Formaggio and C. Toniolo, Eur. J. Org.
Chem., 2002, 2002, 1232–1247; K. Wright, F. Melandri, C. Cannizzo,
M. Wakselman and J.-P. Mazaleyrat, Tetrahedron, 2002, 58, 5811–5820;
F. Formaggio, S. Oancea, C. Peggion, M. Crisma, C. Toniolo, K.
Wright, M. Wakselman and J.-P. Mazaleyrat, Biopolymers, 2003, 71,
667–674; J. P. Mazaleyrat, K. Wright, M.-V. Azzini, A. Gaucher and
M. Wakselman, Tetrahedron Lett., 2003, 44, 1741–1745; A. Gaucher, O.
Barbeau, W. Hamchaoui, L. Vandromme, K. Wright, M. Wakselman
and J.-P. Mazaleyrat, Tetrahedron Lett., 2002, 43, 8241–8244; A.
Gaucher, L. Dutot, O. Barbeau, M. Wakselman and J.-P. Mazaleyrat,
Tetrahedron: Asymmetry, 2005, 16, 857–864.
References
1 I. Cornut, E. Thiaudie`re and J. Dufourcq, in The Amphipathic Helix, ed.
R.M. Epand, CRC Press, Boca Raton, 1993, pp 173–219; G. Saberwal
and R. Nagaraj, Biochim. Biophys. Acta, 1994, 1197, 109–131; W. L.
Maloy and U. P. Kari, Biopolymers, 1995, 37, 105–122; R. M. Kini and
H. J. Evans, Int. J. Pept. Protein Res., 1989, 34, 277–286; A. Tossi, L.
Sandri and A. Giangaspero, Biopolymers, 2000, 55, 4–30.
2 M. Dathe, H. Nikolenko, J. Meyer, M. Beyermann and M. Bienert,
FEBS Lett., 2001, 501, 146–150; M. Dathe, M. Schu¨mann, T. Wieprech,
A. Winkler, M. Beyermann, E. Krause, K. Matsuzaki, O. Murase and
M. Bienert, Biochemistry, 1996, 35, 12612–12622; M. Sharon, Z. Oren,
Y. Shai and J. Anglister, Biochemistry, 1999, 38, 15305–15316; T. Tachi,
R. F. Epand, R. M. Epand and K. Matsuzaki, Biochemistry, 2002, 41,
10723–10731.
3 H. M. Chen, W. Wang, D. Smith and S. C. Chan, Biochim. Biophys.
Acta, 1997, 1336, 171–179; A. Okada, K. Wakamatsu, T. Miyazawa
and T. Higashijima, Biochemistry, 1994, 33, 9438–9448; H. G. Boman,
D. Wade, I. A. Boman, B. Wahlin and R. B. Merrifield, FEBS Lett.,
1989, 259, 103–106; D. Andreu, J. Ubach, A. Boman, B. Wahlin, D.
Wade, R. B. Merrifield and H. G. Boman, FEBS Lett., 1992, 296, 190–
194; D. Wade, D. Andreu, S. A. Mitchell, A. M. V. Silveira, A. Boman,
H. G. Boman and R. B. Merrifield, Int. J. Pept. Protein Res., 1992, 40,
429–436; S. Y. Shin, S.-H. Lee, S.-T. Yang, E. J. Park, D. G. Lee, M. K.
Lee, S. H. Eom, W. K. Song, Y. Kim, K.-S. Hahm and J. I. Kim, J. Pept.
Res., 2001, 58, 504–514.
15 For reviews involving other synthetic ion channels and pores see: G. W.
Gokel and A. Mukhopadhyay, Chem. Soc. Rev., 2001, 30, 274–286;
I. I. Stoikov, I. S. Antipin and A. I. Konovalov, Usp. Khim., 2003, 72,
1190–1214; Koert, L. Al-Momani and J. R. Pfeifer, Synthesis, 2004,
1129–1146; S. Matile, A. Som and N. Sorde, Tetrahedron, 2004, 60,
´
6405–6435.
16 M. Arseneault, F. Otis and N. Voyer, Proc. SPIE-Int. Soc. Opt. Eng.,
2005, 5469, 126–132; F. Otis, N. Voyer, A. Polidori and B. Pucci,
New J. Chem., 2006, 30, 185–190.
17 J. M. Stewart and J. D. Young, in Solid Phase Peptide Synthesis,
ed. J. M. Stewart and J. Dillaha, Pierce Chemical Company, Rockfort,
Illinois, USA, 2nd edn, 1984, page 235.
4 R. P. Cheng, S. H. Gellman and W. F. Degrado, Chem. Rev., 2001,
101, 3219–3232; E. A. Porter, X. Wang, H.-S. Lee, B. Weisblum and
S. H. Gellman, Nature, 2000, 404, 565; E. A. Porter, B. Weisblum and
S. H. Gellman, J. Am. Chem. Soc., 2002, 124, 7324–7330; X. Wang, J. F.
Espinosa and S. H. Gellman, J. Am. Chem. Soc., 2000, 122, 4821–4822.
5 S. Fernandez-Lopez, H.-S. Kim, E. C. Choi, M. Delgado, J. R. Granja,
A. Khasanov, K. Kraehenbuehl, G. Long, D. A. Weinburger, K. M.
Wilcoxen and M. R. Ghadiri, Nature, 2001, 412, 452–455.
6 L. Beven, S. Castano, J. Dufourcq, A. Wieslander and H. Wroblewski,
Eur. J. Biochem., 2003, 270, 2207–2217; S. Castano, B. Desbat and J.
Dufourcq, Biochim. Biophys. Acta, 2000, 1463, 65–80; J. Dufourcq, S.
Castano, I. Cornut, K. Bu¨ttner and J. L. Dasseux, Biochim. Biophys.
Acta, 1999, 1416, 161–175.
18 T. H. Black, Aldrichimica Acta, 1983, 16, 3.
19 S. Takahashi, E.-H. Kim, T. Hibino and T. Ooi, Biopolymers, 1989, 28,
995–1009.
20 T. Benachir and M. Lafleur, Biochim. Biophys. Acta, 1995, 1235, 452–
460.
21 Y. Shai, Biochim. Biophys. Acta, 1999, 1462, 55–70.
22 P. Juwadi, S. Vunnam and R. B. Merrifield, J. Am. Chem. Soc., 1996,
118, 8989–8997.
23 N. Sakai, D. Gerard and S. Matile, J. Am. Chem. Soc., 2001, 123,
2517–2524.
24 W. F. DeGrado and E. T. Kaiser, J. Org. Chem., 1980, 45, 1295–1300;
W. F. DeGrado and E. T. Kaiser, J. Org. Chem., 1982, 47, 3258–
3260.
This journal is
The Royal Society of Chemistry 2007
Org. Biomol. Chem., 2007, 5, 1459–1465 | 1465
©