Cyclohexylether δ-Amino Acids: New Leads for Selectivity Filters in Ion Channels

Angewandte Chemie - International Edition

Volumn 40, Issue 11, 2001, Pages 2076-2078

  Arndt, Hans Dieter ^a   Knoll, Andrea ^a   Koert, Ulrich ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345880684     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20010601)40:11<2076::AID-ANIE2076>3.0.CO;2-G     Document Type: Article

References (51)

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26. β-Peptides: a) D. Seebach, J. L. Matthews, Chem. Commun. 1997, 21, 2015-2022; b) S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180; γ-peptides: c) T. Hintermann, K. Gademann, B. Jaun, D. Seebach, Helv. Chim. Acta 1998, 81, 983-1002; d) S. Hanessian, X. L. Luo, R. Schaum, S. Michnick, J. Am. Chem. Soc. 1998, 120, 8569-8570.
27. β-Peptides: a) D. Seebach, J. L. Matthews, Chem. Commun. 1997, 21, 2015-2022; b) S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180; γ- peptides: c) T. Hintermann, K. Gademann, B. Jaun, D. Seebach, Helv. Chim. Acta 1998, 81, 983-1002; d) S. Hanessian, X. L. Luo, R. Schaum, S. Michnick, J. Am. Chem. Soc. 1998, 120, 8569-8570.
28. β-Peptides: a) D. Seebach, J. L. Matthews, Chem. Commun. 1997, 21, 2015-2022; b) S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180; γ- peptides: c) T. Hintermann, K. Gademann, B. Jaun, D. Seebach, Helv. Chim. Acta 1998, 81, 983-1002; d) S. Hanessian, X. L. Luo, R. Schaum, S. Michnick, J. Am. Chem. Soc. 1998, 120, 8569-8570.
29. As opposed to their β- and γ-counterparts, δ-peptides should generally interact easily with the "natural" α-peptide world. In essence, the α-peptides form a subset of all possible δ-peptides. Examples for δ-peptides can be found in: a) U. Koert, J. Prakt. Chem. 2000, 342, 325-333; b) F. Machetti, A. Ferrali, G. Menchi, E. G. Occhiato, A. Guarna, Org. Lett. 2000, 2, 3987-3990, and references therein.
30. As opposed to their β- and γ-counterparts, δ-peptides should generally interact easily with the "natural" α-peptide world. In essence, the α-peptides form a subset of all possible δ-peptides. Examples for δ-peptides can be found in: a) U. Koert, J. Prakt. Chem. 2000, 342, 325-333; b) F. Machetti, A. Ferrali, G. Menchi, E. G. Occhiato, A. Guarna, Org. Lett. 2000, 2, 3987-3990, and references therein.
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34. Modifications of the sequence and terminal groups of gramicidin A are well studied: a) P. Läuger, Angew. Chem. 1985, 97, 939-959; Angew. Chem. Int. Ed. Engl. 1985, 24, 905-925; b) C.J. Stankovic, S. L. Schreiber, Chemtracts: Org. Chem. 1991, 4, 1-19; c) R. E. Koeppe II, O. S. Andersen, Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 231-258; d) V. Borisenko, D. C. Burns, Z. Zhang, G. A. Woolley, J. Am. Chem. Soc. 2000, 122, 6364-6370. The state of research in the field is presented in Gramicidin and Related Ion Channel-Forming Peptides (Eds.: D. J. Chadwick, G. Cardew), Wiley, Chichester, 1999.
35. Modifications of the sequence and terminal groups of gramicidin A are well studied: a) P. Läuger, Angew. Chem. 1985, 97, 939-959; Angew. Chem. Int. Ed. Engl. 1985, 24, 905-925;
36. Modifications of the sequence and terminal groups of gramicidin A are well studied: a) P. Läuger, Angew. Chem. 1985, 97, 939-959; Angew. Chem. Int. Ed. Engl. 1985, 24, 905-925; b) C.J. Stankovic, S. L. Schreiber, Chemtracts: Org. Chem. 1991, 4, 1-19; c) R. E. Koeppe II, O. S. Andersen, Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 231-258; d) V. Borisenko, D. C. Burns, Z. Zhang, G. A. Woolley, J. Am. Chem. Soc. 2000, 122, 6364-6370. The state of research in the field is presented in Gramicidin and Related Ion Channel-Forming Peptides (Eds.: D. J. Chadwick, G. Cardew), Wiley, Chichester, 1999.
37. Modifications of the sequence and terminal groups of gramicidin A are well studied: a) P. Läuger, Angew. Chem. 1985, 97, 939-959; Angew. Chem. Int. Ed. Engl. 1985, 24, 905-925; b) C.J. Stankovic, S. L. Schreiber, Chemtracts: Org. Chem. 1991, 4, 1-19; c) R. E. Koeppe II, O. S. Andersen, Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 231-258; d) V. Borisenko, D. C. Burns, Z. Zhang, G. A. Woolley, J. Am. Chem. Soc. 2000, 122, 6364-6370. The state of research in the field is presented in Gramicidin and Related Ion Channel-Forming Peptides (Eds.: D. J. Chadwick, G. Cardew), Wiley, Chichester, 1999.
38. Modifications of the sequence and terminal groups of gramicidin A are well studied: a) P. Läuger, Angew. Chem. 1985, 97, 939-959; Angew. Chem. Int. Ed. Engl. 1985, 24, 905-925; b) C.J. Stankovic, S. L. Schreiber, Chemtracts: Org. Chem. 1991, 4, 1-19; c) R. E. Koeppe II, O. S. Andersen, Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 231-258; d) V. Borisenko, D. C. Burns, Z. Zhang, G. A. Woolley, J. Am. Chem. Soc. 2000, 122, 6364-6370. The state of research in the field is presented in Gramicidin and Related Ion Channel-Forming Peptides (Eds.: D. J. Chadwick, G. Cardew), Wiley, Chichester, 1999.
39. d) V. Borisenko, D. C. Burns, Z. Zhang, G. A. Woolley, J. Am. Chem. Soc. 2000, 122, 6364-6370. The state of research in the field is presented in Gramicidin and Related Ion Channel-Forming Peptides (Eds.: D. J. Chadwick, G. Cardew), Wiley, Chichester, 1999.
40. THF-δ-AAs give functional ion channels: A. Schrey, A. Vescovi, A. Knoll, C. Rickert, U. Koert, Angew. Chem. 2000, 112, 928-931; Angew. Chem. Int. Ed. 2000, 39, 900-902.
41. THF-δ-AAs give functional ion channels: A. Schrey, A. Vescovi, A. Knoll, C. Rickert, U. Koert, Angew. Chem. 2000, 112, 928-931; Angew. Chem. Int. Ed. 2000, 39, 900-902.
42. Short minigramicidins from the terminal 11-mer of gA form ion channels dependent on membrane thickness: H.-D. Arndt, A. Knoll, U. Koert, ChemBioChem 2001, 2, 221-223.
43. S.E. Schaus, J.F. Larrow, E. N. Jacobsen, J. Org. Chem. 1997, 62, 4197-4199.
44. M. Pietraszkiewicz, J. Jurczak, Tetrahedron 1984, 40, 2967-2970.
45. 2O).
46. [15| P. Mueller, D, Rudin, Nature 1968, 217, 713-719.
47. 4) did not affect the reversal potentials.
48. Distinct proton-channel activity was only observed at high concentrations, which could indicate that aggregates of these compounds form the active channels. This possibility is under active investigation.
49. + (169 pm).
50. gA proton channels are long lived: S. Cukierman, E. P. Quigley, D. S. Crumrine, Biophys. J. 1997, 73, 2489-2502.
51. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-154390. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (-44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).