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Title: Molecular binding behavior of pyridine-2,6-dicarboxamide-bridged bis(β-cyclodextrin) with oligopeptides : switchable molecular binding mode
Authors: Liu, Yu
Chen, Guo Song
Chen, Yong
Ding, Fei
Liu, Tao
Zhao, Yanli
Keywords: DRNTU::Science::Biological sciences::Biochemistry
Issue Date: 2004
Source: Liu, Y., Chen, G. S., Chen, Y., Ding, F., Liu, T., & Zhao, Y. L. (2004). Molecular Binding Behavior of Pyridine-2,6-dicarboxamide-Bridged Bis(β-cyclodextrin) with Oligopeptides: Switchable Molecular Binding Mode. Bioconjugate Chemistry, 15(2), 300-306.
Series/Report no.: Bioconjugate chemistry
Abstract: Bridged bis(β-cyclodextrin) 1 with a pyridine-2,6-dicarboxamide linker was synthesized, and its inclusion complexation behavior with some aliphatic oligopeptides was investigated in aqueous buffer solution of pH 2.0 and 7.2 at 25 °C by means of circular dichroism, fluorescence, and 2D NMR techniques. The results show that the resulting inclusion complexes of 1 with oligopeptides adopt a cooperative “cyclodextrin-guest-cyclodextrin” sandwich binding mode in a neutral media, but a “guest-linker-cyclodextrin” coinclusion binding mode in an acidic media. These switchable binding modes consequently rationalize the binding ability of bis(β -cyclodextrin) 1 at different pH values; that is, 1 shows the stronger association with oligopeptides in a neutral media. Because of the simultaneous contributions of hydrophobic, hydrogen bond, and electrostatic interactions, bis(β-cyclodextrin) 1 affords length-selectivity up to 4.7 for the Gly-Gly/Gly-Gly-Gly pair at pH 2.0 and sequence-selectivity up to 4.2 for the Gly-Leu/Leu-Gly pair at pH 7.2. These phenomena are discussed from the viewpoint of the size-fit concept and the multipoint recognitions between host and guest.
DOI: 10.1021/bc034230p
Rights: © 2004 American Chemical Society.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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