PMID: 11325262Apr 28, 2001Paper

Molecular design and synthesis of artificial ion channels based on cyclic peptides containing unnatural amino acids

The Journal of Organic Chemistry
H IshidaY Inoue

Abstract

A series of novel cyclic peptides composed of 3 to 5 dipeptide units with alternating natural-unnatural amino acid units, have been designed and synthesized, employing 5-(N-alkanoylamino)-3-aminobenzoic acid with a long alkanoyl chain as the unnatural amino acid. All cyclic peptides with systematically varying pore size, shape, and lipophilicity are found to form ion channels with a conductance of ca. 9 pS in aqueous KCl (500 mM) upon examination by the voltage clamp method. These peptide channels are cation selective with the permeability ratio P(Cl(-))/P(K(+)) of around 0.17. The ion channels formed by the neutral, cationic, and anionic cyclic peptides containing L-alanine, L-lysine, and L-aspartate, respectively, show the monovalent cation selectivity with the permeability ratio P(Na(+))/P(K(+)) of ca. 0.39. On the basis of structural information provided by voltage-dependent blockade of the single channel current of all the tested peptides by Ca(2+), we inferred that each channel is formed from a dimer of the peptide with its peptide ring constructing the channel entrance and its alkanoyl chains lining across the membrane to build up the channel pore. The experimental results are consistent with an idea that the rate of ion...Continue Reading

References

Jan 30, 1991·Biochimica Et Biophysica Acta·C J StankovicS L Schreiber
Oct 1, 1991·The Journal of Membrane Biology·K Nomura, M Sokabe
Jan 1, 1986·Annual Review of Biophysics and Biophysical Chemistry·D G Levitt
Jun 1, 1973·The Journal of General Physiology·A M Woodhull
Jan 23, 1997·Nature·A J MinnC B Thompson
May 1, 1997·Biophysical Journal·C KadukM Bienert

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Citations

Dec 16, 2004·Angewandte Chemie·Lei Wang, Peter G Schultz
Sep 17, 2008·Journal of Molecular Modeling·Gopalan Praveena, Ponmalai Kolandaivel
Mar 10, 2005·Chemical Communications : Chem Comm·Tomoko OkadaMitsuhiko Shionoya
May 9, 2012·IET Nanobiotechnology·H Pradeep, G K Rajanikant
Jun 6, 2009·Journal of Biomolecular Structure & Dynamics·G Praveena, P Kolandaivel
Mar 11, 2010·IEEE Transactions on Nanobioscience·Gopalan Praveena, Ponmalai Kolandaivel
Dec 10, 2016·Journal of the American Chemical Society·Tanmoy SahaPinaki Talukdar
Aug 18, 2006·Chembiochem : a European Journal of Chemical Biology·Hitoshi IshidaShigero Oishi
Sep 21, 2007·Molecular BioSystems·Naomi SakaiStefan Matile
Nov 27, 2002·Science Progress·Peter J Cragg
Aug 18, 2005·Chemistry : a European Journal·Manuel AmorínJuan R Granja
Oct 26, 2005·Angewandte Chemie·Nandita MadhavanMary S Gin
Jan 31, 2006·Angewandte Chemie·Susan E Gibson, Cristina Lecci
Apr 23, 2011·Physical Chemistry Chemical Physics : PCCP·Bin ZhuDongsheng Xu
Jun 22, 2011·Chemical Society Reviews·Jonathan K W Chui, Thomas M Fyles
Jan 27, 2009·Chemical Society Reviews·Stefan Kubik
Apr 29, 2008·Journal of the American Chemical Society·Akiharu SatakeYoshiaki Kobuke
Sep 8, 2011·Journal of the American Chemical Society·Rami HouraniTing Xu
Sep 10, 2014·Journal of the American Chemical Society·Tanmoy SahaPinaki Talukdar
Oct 20, 2005·Journal of the American Chemical Society·Christine A WinschelVladimir Sidorov
Sep 27, 2003·The Journal of Organic Chemistry·Hai HuangJin-Pei Cheng
Aug 18, 2001·Science·M SanoS Shinkai

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