Design, synthesis, and structural analysis of turn modified cyclo-(αβ3αβ2α)2 peptide derivatives toward crystalline hexagon-shaped cationic nanochannel assemblies
作者： José M Otero , Matthijs van der Knaap , Antonio L Llamas-Saiz , Mark J van Raaij , Manuel Amorín
DOI: 10.1021/CG4007108
关键词:
摘要: Intrigued by the not fully extended hairpin monomeric structure of previously reported cyclo-(αβ3αβ 2α)2 peptide 2, as well its nanochannel crystallographic assembly, we here investigate structural properties a series turn derivatives (3-17). Five structures symmetric and asymmetric cyclo- (αβ3αβ2α)2 peptides 3-17 are found; novel saddlelike (4 16) twisted (6) conformers, hairpins 7 14. The pentafluorophenyl/1-naphthyl pentafluorophenyl/9-phenanthryl 14, respectively, adopt anticipated hexagon-shaped crystalline nanotube assemblies, resembling crystal packing parent 2. analysis compounds described can serve basis for biological applications, such design β-sheet mimics or development functional nanomaterials. © 2013 American Chemical Society.
acs.org
sci-hub.se 参考文章(50)
Rituparna S. Roy, Hosahudya N. Gopi, S. Raghothama, Richard D. Gilardi, Isabella L Karle, Padmanabhan Balaram, Peptide Hairpins with Strand Segments Containing α- and β- Amino Acid Residues : Cross – Strand Aromatic Interactions of Facing Phe Residues. Biopolymers. ,vol. 80, pp. 787- 799 ,(2005) , 10.1002/BIP.20294
Robert Günther, Hans-Jörg Hofmann, Krzysztof Kuczera, Searching for Periodic Structures in β-Peptides Journal of Physical Chemistry B. ,vol. 105, pp. 5559- 5567 ,(2001) , 10.1021/JP010021V
Jinghui Luo, José M Otero, Chien‐Hung Yu, Sebastian KTS Wärmländer, Astrid Gräslund, Mark Overhand, Jan Pieter Abrahams, None, Inhibiting and reversing amyloid-β peptide (1-40) fibril formation with gramicidin S and engineered analogues. Chemistry: A European Journal. ,vol. 19, pp. 17338- 17348 ,(2013) , 10.1002/CHEM.201301535
G. F. GAUSE, M. G. BRAZHNIKOVA, Gramicidin S and its use in the Treatment of Infected Wounds Nature. ,vol. 154, pp. 703- 703 ,(1944) , 10.1038/154703A0
Susanne Krauthäuser, Laurie A. Christianson, Douglas R. Powell, Samuel H. Gellman, Antiparallel Sheet Formation in β-Peptide Foldamers: Effects of β-Amino Acid Substitution on Conformational Preference1 Journal of the American Chemical Society. ,vol. 119, pp. 11719- 11720 ,(1997) , 10.1021/JA9730627
Xavier Daura, Karl Gademann, Heiko Schäfer, Bernhard Jaun, Dieter Seebach, Wilfred F. van Gunsteren, The beta-peptide hairpin in solution: conformational study of a beta-hexapeptide in methanol by NMR spectroscopy and MD simulation. Journal of the American Chemical Society. ,vol. 123, pp. 2393- 2404 ,(2001) , 10.1021/JA003689G
Alan C. Gibbs, Leslie H. Kondejewski, Wolfram Gronwald, Alex M. Nip, Robert S. Hodges, Brian D. Sykes, David S. Wishart, Unusual β-sheet periodicity in small cyclic peptides Nature Structural & Molecular Biology. ,vol. 5, pp. 284- 288 ,(1998) , 10.1038/NSB0498-284
M. Reza Ghadiri, Juan R. Granja, Ronald A. Milligan, Duncan E. McRee, Nina Khazanovich, Self-assembling organic nanotubes based on a cyclic peptide architecture Nature. ,vol. 366, pp. 324- 327 ,(1993) , 10.1038/366324A0
Rituparna S. Roy, Hosahudya N. Gopi, Srinivasarao Raghothama, Isabella L. Karle, Padmanabhan Balaram, Hybrid Peptide Hairpins Containing α‐ and ω‐Amino Acids: Conformational Analysis of Decapeptides with Unsubstituted β‐, γ‐, and δ‐Residues at Positions 3 and 8 Chemistry: A European Journal. ,vol. 12, pp. 3295- 3302 ,(2006) , 10.1002/CHEM.200500742
John A. Robinson, β-Hairpin Peptidomimetics: Design, Structures and Biological Activities Accounts of Chemical Research. ,vol. 41, pp. 1278- 1288 ,(2008) , 10.1021/AR700259K