Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2004(8): 1129-1146
DOI: 10.1055/s-2004-822385
DOI: 10.1055/s-2004-822385
REVIEW
© Georg Thieme Verlag Stuttgart · New YorkSynthetic Ion Channels
Further Information
Received
4 March 2004
Publication Date:
19 May 2004 (online)
Publication History
Publication Date:
19 May 2004 (online)
Abstract
Progress in the synthesis of membrane-bound ion channels is reviewed. Important results from several groups are highlighted and contributions from the authors’ group are summarized. Topics covered include synthetic approaches towards oligo-THF amino acids, oligopyrrolidines and gramicidin hybrid channels. Points of interest are the importance of self-assembly systems, the functional analysis (ion selectivity, gating, asymmetric insertion and asymmetric function) and the structural characterization of the channel.
1 Introduction
2 Polyether-Containing Ion Channels
3 Peptide β-Helix as Ion Channel Motif
4 Ion Selectivity in Synthetic Ion Channels
5 THF-Gramicidin Hybrid Channels and Asymmetric Insertion into the Membrane
6 Minigramicidins: Hydrophobic Match/Mismatch with the Membrane and a Conformational Switch
7 Synthetic Ion Channels by Self-Assembly of the Pore
8 Outlook
Key words
synthetic ion channels - gramicidin hybrids - amino acids - bioorganic chemistry - supramolecular chemistry
- 1a
Hille B. Ion Channels of Excitable Membranes 3rd Ed: Sinauer; Sunderland MA: 2001. - 1b
Skou JC. Angew. Chem. Int. Ed. 1998, 37: 2320 - 2a
Doyle D.Cabral JM.Pfuetzner RA.Kuo A.Gulbis JM.Cohen SL.Chait BT.MacKinnon R. Science 1998, 280: 69 - 2b
Toyoshima C.Nakasako M.Nomura H.Ogawa H. Nature 2000, 405: 647 - 2c
Jiang Y.Lee A.Chen J.Cadene M.Chait BT.MacKinnon R. Nature 2002, 417: 523 - 2d
Jiang Y.Lee A.Chen J.Cadene M.Chait BT.MacKinnon R. Nature 2002, 417: 515 - 2e
Dutzler R.Campbell EB.Cadene M.Chait BT.MacKinnon R. Nature 2002, 415: 287 - 2f
Ruta V.Jiang Y.Lee A.Chen J.MacKinnon R. Nature 2003, 422: 180 - 2g
Jiang Y.Lee A.Ruta V.Cadene M.Chait BT.MacKinnon R. Nature 2003, 423: 33 - 2h
Jiang Y.Ruta V.Chen J.Lee A.MacKinnon R. Nature 2003, 423: 42 - 2i
Miyazawa A.Fujiyoshi Y.Unwin N. Nature 2003, 423: 949 - 2j
Dutzler R.Campbell EB.MacKinnon R. Science 2003, 300: 108 - 2k
Valiyaveetil FI.MacKinnon R.Muir TW. J. Am. Chem. Soc. 2002, 124: 9113 - 3a
Gokel GW.Mukhopadhyay A. Chem. Soc. Rev. 2001, 30: 274 - 3b
Kobuke Y. In Advances in Supramolecular Chemistry Vol. 4:Gokel GW. JAI-Press; Greenwich: 1997. p.163-210 - 3c
Voyer N. Top. Curr. Chem. 1996, 184: 1 - 3d
Bayley H.Martin CR. Chem. Rev. 2000, 100: 2575 - 3e
Koert U. Chem. unserer Zeit 1997, 31: 20 - 3f
Cross GG.Fyles TM.James TD.Zojaji M. Synlett 1993, 449 - 3g
Ackerfeldt KS.Lear JD.Wasserman ZR.Chung LA.DeGrado WF. Acc. Chem. Res. 1993, 26: 191 - 4
Gokel G. Crown Ethers & Cryptands, Monographs in Supramolecular ChemistryStoddart JF. Royal Society; Birmingham: 1994. - 5a
Gokel GW.Ferdani R.Liu J.Pajewski R.Shabany H.Utrecht P. Chem.-Eur. J. 2001, 7: 33 - 5b
Schlesinger PH.Ferdani R.Liu J.Pajewska J.Pajewski R.Saito M.Shabany H.Gokel GW. J. Am. Chem. Soc. 2002, 124: 1848 - 6
Leevy WM.Donato GM.Ferdani R.Goldman WE.Schlesinger PH.Gokel GW. J. Am. Chem. Soc. 2002, 124: 9022 - 7a
Meillon J.-C.Voyer N. Angew. Chem., Int. Ed. Engl. 1997, 36: 967 - 7b
Voyer N.Robitaille M. J. Am. Chem. Soc. 1995, 117: 6599 - 8
Hall AC.Suarez C.Hom-Choudry A.Manu ANA.Hall CD.Kirkovits GJ.Ghirivaga I. Org. Biomol. Chem. 2003, 1: 2973 - 9a
Lehn J.-M.Potvin PG. Can. J. Chem. 1988, 66: 195 - 9b
Pregel MJ.Jullien L.Lehn J.-M. Angew. Chem., Int. Ed. Engl. 1992, 31: 1637 - 9c
Canceill J.Jullien J.Lacomne L.Lehn J.-M. Helv. Chim. Acta 1992, 75: 791 - 10a
Fyles TM.Loock D.Zhou X. J. Am. Chem. Soc. 1998, 120: 2997 - 10b
Fyles TM.Loock D.Zhou X. Can. J. Chem. 1998, 76: 1015 - 10c
Fyles TM.Hu C.-W.Knoy R. Org. Lett. 2001, 3: 1335 - 10d
Cameron LM.Fyles TM.Hu C.-W. J. Org. Chem. 2002, 67: 1548 - 11
Tabushi I.Kuroda Y.Yokota K. Tetrahedron Lett. 1982, 23: 4601 - 12
Koert U.Stein M.Harms K. Angew. Chem., Int. Ed. Engl. 1994, 33: 1180 - 13a
Koert U.Stein M.Harms K. Tetrahedron Lett. 1993, 34: 2299 - 13b
Koert U.Stein M.Harms K. Liebigs Ann. 1995, 1415 - 14
Wagner H.Koert U. Angew. Chem., Int. Ed. Engl. 1994, 33: 1873 - 15
Koert U.Stein M.Wagner H. Chem.-Eur. J. 1997, 3: 1170 - 16
Koert U. Synthesis 1995, 115 - 17
Wagner H.Harms K.Koert U.Meder S.Boheim G. Angew. Chem., Int. Ed. Engl. 1996, 35: 2643 - 18
Schrey A.Osterkamp F.Straudi A.Rickert C.Wagner H.Koert U.Herrschaft B.Harms K. Eur. J. Org. Chem. 1999, 64: 2977 - 19
Arndt H.-D.Polborn K.Koert U. Tetrahedron Lett. 1997, 38: 3879 - 20
Arndt H.-D.Welz R.Müller S.Ziemer B.Koert U. Chem.-Eur. J. accepted for publication - 21
Urry DW. Proc. Natl. Acad. Sci. U.S.A. 1971, 68: 672 - 22
Gramicidin and Related Ion Channel-Forming Peptides
Chadwick DJ.Cardew G. Wiley; Chichester: 1999. - 23a
Koeppe RE.Andersen OS. Annu. Rev. Biophys. Biomol. Struct. 1996, 25: 231 - 23b
Schreiber SL.Stankovich CJ.Heinemann S.Delfino JM.Sigworth FJ. Science 1989, 244: 813 - 23c
Stankovic CJ.Schreiber SL. Chemtracts: Org. Chem. 1991, 4: 1 - 23d
Läuger P. Angew. Chem., Int. Ed. Engl. 1985, 24: 905 - 23e
Barsukov IL.Lomize AL.Arseniev AS.Bystrov VF. Biol. Membr. 1987, 4: 171 - 24a
Ivanov VT.Fonina LA.Savelov IS.Demina AM.Havalachek YA.Sychev SV.Irkhyn AI.Kaplanskaya MB.Melnik EI.Ochinnikow YA. Pept. Struct. Biol. Funct., Proc. Am. Pept. Symp., 6th 1979, 655 - 24b
Arseniev AS.Barsukov IL.Byrstrov VF.Lomize AL.Ovchinnikov YA. FEBS Lett. 1985, 186: 168 - 24c
Andersen OS.Apell HJ.Bamberg E.Busath DD.Koeppe RE.Sigworth FJ.Szabo G.Urry DW.Woolley A. Nat. Struct. Biol. 1999, 6: 609 - 24d
Cross TA.Arseniev A.Cornell BA.Davis JH.Killian JA.Koeppe RE.Nicholson LK.Separovic F.Wallace BA. Nat. Struct. Biol. 1999, 6: 610 - 24e
Burkhart BM.Duax WL. Nat. Struct. Biol. 1999, 6: 611 - 24f
Wallace BA. J. Struct. Biol. 1998, 121: 123 - 25a
Ketchem RR.Hu W.Cross TA. Science 1993, 261: 1457 - 25b
Kovacs F.Quine J.Cross TA. Proc. Natl. Acad. Sci. U.S.A. 1999, 96: 7910 - 25c
Allen TW.Andersen OS.Roux B. J. Am. Chem. Soc. 2003, 125: 9868 - 26
Arndt H.-D.Knoll A.Koert U. Angew. Chem. Int. Ed. 2001, 40: 2076 - 27
Tanaka Y.Kobuke Y.Sokabe M. Angew. Chem., Int. Ed. Engl. 1995, 34: 693 - 28
Yoshino N.Satake A.Kobuke Y. Angew. Chem. Int. Ed. 2001, 40: 457 - 29
Wright AJ.Matthews SE.Fischer WB.Beer PD. Chem.-Eur. J. 2001, 7: 3474 - 30a
Vescovi A.Knoll A.Koert U. Org. Biomol. Chem. 2003, 1: 2983 - 30b
Schrey A.Vescovi A.Knoll A.Rickert C.Koert U. Angew. Chem. Int. Ed. 2000, 39: 900 - 30c
Fidzinski P.Knoll A.Rosenthal R.Schrey A.Vescovi A.Koert U.Wiederholt M.Strauß O. Chem. Biol. 2003, 10: 35 - 31
Arndt H.-D.Vescovi A.Schrey A.Pfeifer JR.Koert U. Tetrahedron 2002, 58: 2789 - 32
Arndt H.-D.Knoll A.Koert U. ChemBioChem 2001, 221 - 33
Arndt H.-D.Bockelmann D.Knoll A.Lamberth S.Griesinger C.Koert U. Angew. Chem. Int. Ed. 2002, 41: 4062 - 34
Borisenko V.Burns DC.Zhang Z.Woolley GA. J. Am. Chem. Soc. 2000, 122: 6364 - 35
Lougheed T.Borisenko V.Hand CE.Woolley GA. Bioconjugate Chem. 2001, 12: 594 - 36
Lien L.Jaikaran DC.Zhang Z.Woolley GA. J. Am. Chem. Soc. 1996, 118: 12222 - 37
Sun X.Lorenzi GP. Helv. Chim. Acta 1994, 77: 1520 - 38a
Ghadiri MR.Granja JR.Buehler LK. Nature 1994, 369: 301 - 38b
Clark TD.Buehler LK.Ghadiri MR. J. Am. Chem. Soc. 1998, 120: 651 - 39
Seebach D.Matthews JL.Meden A.Wessels T.Baerlocher C.McCusker LB. Helv. Chim. Acta 1997, 80: 173 - 40
Amorin M.Castedo L.Granja JR. J. Am. Chem. Soc. 2003, 125: 2844 - 41a
Das S.Seebach D.Reusch RN. Biochemistry 2002, 41: 5307 - 41b
Seebach D.Brunner A.Bürger HM.Reusch RN.Bramble LL. Helv. Chim. Acta 1996, 79: 507 - 42a
Sakai N.Matile S. Chem. Commun. 2003, 2514 - 42b
Matile S. Chem. Soc. Rev. 2001, 30: 158 - 43a
Baumeister B.Sakai N.Matile S. Angew. Chem. Int. Ed. 2000, 39: 1955 - 43b
Sakai N.Matile S. J. Am. Chem. Soc. 2002, 124: 1184 - 43c
Sakai N.Sorde N.Das G.Perrottet P.Gerard D.Matile S. Org. Biomol. Chem. 2003, 1: 1226 - 44
Winum JY.Matile S. J. Am. Chem. Soc. 1999, 121: 7961 - 45a
Fyles TM.Loock D.Zhou X. J. Am. Chem. Soc. 1998, 120: 2997 - 45b
Fyles TM.Loock D.Zhou X. Can. J. Chem. 1998, 76: 1015 - 46
Fyles TM.Hu C.-W.Knoy R. Org. Lett. 2001, 3: 1335 - 47
Cameron LM.Fyles TM.Hu C.-W. J. Org. Chem. 2002, 67: 1548 - 48a
Kobuke Y.Nagatani T. J. Org. Chem. 2001, 66: 5094 - 48b
Goto C.Yamamura M.Satake A.Kobuke Y. J. Am. Chem. Soc. 2001, 123: 12152 - 49
Kobuke Y.Ueda K.Sokabe M. Chem. Lett. 1995, 435 - 50a
Yamaji N.Matsumori N.Matsuoka S.Oishi T.Murata M. Org. Lett. 2002, 4: 2087 - 50b
Matsumori N.Yamaji N.Matsuoka S.Oishi T.Murata . J. Am. Chem. Soc. 2002, 124: 4180 - 50c
Mickus DE.Levitt DG.Rychnovsky SC. J. Am. Chem. Soc. 1992, 114: 359 - 50d
Stadler E.Dedek P.Yamashita K.Regen SL. J. Am. Chem. Soc. 1994, 116: 6677 - 51a
Perez C.Espinola CG.Foces-Foces C.Nunez-Coello P.Carrasco H.Martin JD. Org. Lett. 2000, 2: 1185 - 51b
Renkes T.Schäfer HJ.Siemens PM.Neumann E. Angew. Chem. Int. Ed. 2000, 39: 2512 - 52
Sidorov V.Kotch FW.Abdrakhmanova G.Mizani R.Fettinger JC.Davis JT. J. Am. Chem. Soc. 2002, 124: 2267 - 53
Terrettaz S.Ulrich W.-P.Guerrini R.Verdini A.Vogel H. Angew. Chem. 2001, 113: 1788 - 54a
Futaki S.Fukuda M.Omote M.Yamauchi K.Yagami T.Niwa M.Sugiura Y. J. Am. Chem. Soc. 2001, 123: 12127 - 54b
You S.Peng S.Lien L.Breed J.Sansom MSP.Woolley GA. Biochemistry 1996, 35: 6225 - 54c
Wassner AJ.Hurt JA.Lear JD.Akerfeldt KS. Org. Lett. 2002, 4: 1647 - 54d
Kaduk C.Duclohier H.Dathe M.Wenschuh H.Beyermann M.Molle G.Bienert M. Biophys. J. 1997, 72: 2151 - 55
Cornell BA.Braach-Maksvytis VLB.King LG.Osman PDJ.Raguse B.Wieczorek L.Pace RJ. Nature 1997, 387: 580 - 56a
Gu LQ.Braha O.Conlan S.Cheley S.Bayley H. Nature 1999, 398: 686 - 56b
Bayley H.Cremer PS. Nature 2001, 413: 226 - 57
Das G.Talukdar P.Matile S. Science 2002, 298: 1600