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Design of a turn-linker-turn foldamer by incorporating meta-amino benzoic acid in the middle of a helix forming hexapeptide sequence: A helix breaking approach

Dutta, A., Drew, M. G. B. and Pramanik, A. (2009) Design of a turn-linker-turn foldamer by incorporating meta-amino benzoic acid in the middle of a helix forming hexapeptide sequence: A helix breaking approach. Journal of Molecular Structure, 930 (1-3). pp. 55-59. ISSN 0022-2860

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To link to this item DOI: 10.1016/j.molstruc.2009.04.037

Abstract/Summary

Single crystal X-ray diffraction studies reveal that the incorporation of meta-amino benzoic acid in the middle of a helix forming hexapeptide sequence such as in peptide I Boc-Ile(1)-Aib(2)-Val(3)-m-ABA(4)-Ile(5)-Aib(6)-Leu(7)-OMe (Aib: alpha-amino isobutyric acid: m-ABA: meta-amino benzoic acid) breaks the helix propagation to produce a turn-linker-turn (T-L-T) foldamer in the solid state. In the crystalline state two conformational isomers of peptide I self-assemble in antiparallel fashion through intermolecular hydrogen bonds and aromatic pi-pi interactions to form a molecular duplex. The duplexes are further interconnected through intermolecular hydrogen bonds to form a layer of peptides. The layers are stacked one on top of the other through van der Waals interactions to form hydrophilic channels filled with solvent methanol. (C) 2009 Elsevier B.V. All rights reserved.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11237
Uncontrolled Keywords:Peptide, beta-Turn, Foldamer, Self-assembly, Duplex, Channels, CRYSTAL-STRUCTURES, PEPTIDE HELICES, MODEL PEPTIDES, AMINOISOBUTYRIC-ACID, CORNER RESIDUES, SOLID-STATE, TRIPEPTIDES, PROTEINS, CONFORMATIONS, SEGMENTS

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