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Title: Design, synthesis and structural analysis of mixed α/β-peptides that adopt stable cyclic hairpin-like conformations
Authors: Van Der Knaap, M.
Otero, J.M.
Llamas-Saiz, A.
Van Raaij, M.J.
Lageveen, L.I.
Busscher, H.J.
Grotenbreg, G.M. 
Van Der Marel, G.A.
Overkleeft, H.S.
Overhand, M.
Keywords: Cyclic mixed α/β-peptides
H-bonding pattern
Hairpin-like structure
Issue Date: 11-Mar-2012
Citation: Van Der Knaap, M., Otero, J.M., Llamas-Saiz, A., Van Raaij, M.J., Lageveen, L.I., Busscher, H.J., Grotenbreg, G.M., Van Der Marel, G.A., Overkleeft, H.S., Overhand, M. (2012-03-11). Design, synthesis and structural analysis of mixed α/β-peptides that adopt stable cyclic hairpin-like conformations. Tetrahedron 68 (10) : 2391-2400. ScholarBank@NUS Repository.
Abstract: The strategic replacement of four α-amino acid residues of a cyclo-(ααααα) 2 peptide by β-, β 2- or β 3-amino acids residues provided a series of novel 2:1 α/β-mixed peptides that were designed to adopt cyclic hairpin-like structures. It was shown that conformationally stable cyclo-(αβαβα) 2 isomers can be obtained using both enantiomers of the central two basic α-amino acid residues, a known α-amino acid turn sequence and several combinations of facing β-amino acid residues with no side chain or a hydrophobic side chain having specific regio- and stereochemistry. The X-ray analysis of two derivatives provides molecular details of the intra-molecular hydrogen bonding interaction, dihedral angles of the backbone and side chain positioning of the novel cyclic hairpin-like structures. One of these isomers forms an unprecedented hexagon-shaped nano-channel assembly in the crystal structure. Well-defined cyclic hairpin-like structures as described here and derivatives that can be readily designed based on this research can be used as scaffolds onto which functional groups can be grafted in a spatially controlled manner and as β-hairpin mimics with specific biological properties. © 2012 Elsevier Ltd. All rights reserved.
Source Title: Tetrahedron
ISSN: 00404020
DOI: 10.1016/j.tet.2012.01.015
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