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Kobuke, Y.1
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Fyles, T. M.; van Straaten-Nijenhuis, W.F. In Comprehensive Supramolecular Chemistry; Reinhoudt, D.N., Ed.; Elsevier Science: Oxford, 1996; Vol. 10, pp 53-77.
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Recent contributions: (a) Schrey, A.; Vescovi, A.; Knoll, A.; Rickert, C.; Koert, U. Angew. Chem., Int. Ed. Engl. 2000, 39, 900-902.
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(h) Murillo, O.; Suzuki, I.; Abel, E.; Murray, C.L.; Meadows, E.S.; Jin, T.; Gokel, G.W. J. Am. Chem. Soc. 1997, 119, 5540-5549.
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(i) Murray, C.L.; Meadows, E.S.; Murillo, O.; Gokel, G.W. J. Am. Chem. Soc. 1997, 119, 7887-7888.
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(j) Weiss, L.A.; Sakai, N.; Ghabremariam, B.; Ni, C.; Matile, S. J. Am. Chem. Soc. 1997, 119, 12142-12149.
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(l) Pechulis, A.D.; Thompson, R.J.; Fojtik, J.P.; Schwartz, H.M.; Lisek, C.A.; Frye, L.L. Biorg. Med. Chem. 1997, 5, 1893-1901.
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(m) Fyles, T.M.; Loock, D.; van Straaten-Nijenhuis, W.F.; Zhou, X. J. Org. Chem. 1996, 61, 8866-8874.
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The spontaneous incorporation of 1a-1f in lipid membranes is caused by both the hydrophobic section of the fatty acid chain and the cationic π-interaction of the benzyl groups with the choline group of the lipid: Renkes, T.; Shäfer, H.J.; Siemens, P.M.; Neumann, E. Angew. Chem.. Int. Ed. Engl. 2000, 39, 2512-2516.
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Length was calculated by molecular modeling and refers to the distance among pyran oxygens in fully extended polyoxyethylene chains
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Length was calculated by molecular modeling and refers to the distance among pyran oxygens in fully extended polyoxyethylene chains.
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2O (86.8 mL), pH 7.67), and then vortexed to suspend the lipid. The suspension was sonicated using a probe for 30-60 min until clarity was obtained. The untrapped dye was removed by size-exclusion chromatography (Sepharose CL 4B) using the same phosphate buffer. The lipid concentration of the resulting vesicle solution was estimated by measuring the phosphate content after digestion (Steward, J.H. Anal. Biochem. 1980, 104, 10-14) and the enclosed HPTS concentration by fluorescence spectroscopy by comparing the emission with known concentrations of free HPTS. Transport was initiated by an imposed pH gradient (pH 7.67 inside, pH 6.4 outside). Control experiments established that there was no proton flux without the addition of transporter, no detergent effect of the transporter on the vesicles, and that vesicles remained intact at the end of each experiment.
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2O (86.8 mL), pH 7.67), and then vortexed to suspend the lipid. The suspension was sonicated using a probe for 30-60 min until clarity was obtained. The untrapped dye was removed by size-exclusion chromatography (Sepharose CL 4B) using the same phosphate buffer. The lipid concentration of the resulting vesicle solution was estimated by measuring the phosphate content after digestion (Steward, J.H. Anal. Biochem. 1980, 104, 10-14) and the enclosed HPTS concentration by fluorescence spectroscopy by comparing the emission with known concentrations of free HPTS. Transport was initiated by an imposed pH gradient (pH 7.67 inside, pH 6.4 outside). Control experiments established that there was no proton flux without the addition of transporter, no detergent effect of the transporter on the vesicles, and that vesicles remained intact at the end of each experiment.
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For representative examples of this approach, see the monomer systems of Tabushi (Tabushi, I.; Kuroda, Y.; Yokota, K. Tetrahedron Lett. 1982, 4601-4604); Menger (Menger, F.M.; Davis, D.S.; Persichetti, R.A.; Lee, J.-J. J. Am. Chem. Soc. 1990, 112, 2451-2452), Kobuke (Tanaka, Y.; Kobuke, Y.; Sokabe, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 693-694); Regen (Deng, G.; Merritt, M.; Yamashita, K.; Janout, V.; Sadownik, A.; Regen, S.L. J. Am. Chem. Soc. 1996, 118, 3307-3308).
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Tabushi, I.1
Kuroda, Y.2
Yokota, K.3
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35
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0025246133
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For representative examples of this approach, see the monomer systems of Tabushi (Tabushi, I.; Kuroda, Y.; Yokota, K. Tetrahedron Lett. 1982, 4601-4604); Menger (Menger, F.M.; Davis, D.S.; Persichetti, R.A.; Lee, J.-J. J. Am. Chem. Soc. 1990, 112, 2451-2452), Kobuke (Tanaka, Y.; Kobuke, Y.; Sokabe, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 693-694); Regen (Deng, G.; Merritt, M.; Yamashita, K.; Janout, V.; Sadownik, A.; Regen, S.L. J. Am. Chem. Soc. 1996, 118, 3307-3308).
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J. Am. Chem. Soc.
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Menger, F.M.1
Davis, D.S.2
Persichetti, R.A.3
Lee, J.-J.4
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36
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33745145455
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For representative examples of this approach, see the monomer systems of Tabushi (Tabushi, I.; Kuroda, Y.; Yokota, K. Tetrahedron Lett. 1982, 4601-4604); Menger (Menger, F.M.; Davis, D.S.; Persichetti, R.A.; Lee, J.-J. J. Am. Chem. Soc. 1990, 112, 2451-2452), Kobuke (Tanaka, Y.; Kobuke, Y.; Sokabe, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 693-694); Regen (Deng, G.; Merritt, M.; Yamashita, K.; Janout, V.; Sadownik, A.; Regen, S.L. J. Am. Chem. Soc. 1996, 118, 3307-3308).
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Angew. Chem., Int. Ed. Engl.
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Tanaka, Y.1
Kobuke, Y.2
Sokabe, M.3
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37
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0030567334
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For representative examples of this approach, see the monomer systems of Tabushi (Tabushi, I.; Kuroda, Y.; Yokota, K. Tetrahedron Lett. 1982, 4601-4604); Menger (Menger, F.M.; Davis, D.S.; Persichetti, R.A.; Lee, J.-J. J. Am. Chem. Soc. 1990, 112, 2451-2452), Kobuke (Tanaka, Y.; Kobuke, Y.; Sokabe, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 693-694); Regen (Deng, G.; Merritt, M.; Yamashita, K.; Janout, V.; Sadownik, A.; Regen, S.L. J. Am. Chem. Soc. 1996, 118, 3307-3308).
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J. Am. Chem. Soc.
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Deng, G.1
Merritt, M.2
Yamashita, K.3
Janout, V.4
Sadownik, A.5
Regen, S.L.6
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39
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