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Title: Binding behavior of aliphatic oligopeptides by bridged and metallobridged bis(β-cyclodextrin)s bearing an oxamido bis(2-benzoic) carboxyl linker
Authors: Liu, Yu
Zhao, Yanli
Chen, Yong
Ding, Fei
Chen, Guo Song
Keywords: DRNTU::Science::Biological sciences::Biochemistry
Issue Date: 2004
Source: Liu, Y., Zhao, Y. L., Chen, Y., Ding, F., & Chen, G. S. (2004). Binding Behavior of Aliphatic Oligopeptides by Bridged and Metallobridged Bis(β-cyclodextrin)s Bearing an Oxamido Bis(2-benzoic) Carboxyl Linker. Bioconjugate Chemistry, 15(6), 1236-1245.
Series/Report no.: Bioconjugate Chemistry
Abstract: β-Cyclodextrin dimers bearing an oxamido bis(2-benzoic) carboxyl linker (1) or its metal complexes (2) and 3) were newly synthesized, and their inclusion complexation behavior with a series of representative aliphatic oligopeptides, i.e., Leu-Gly, Gly-Leu, Gly-Pro, Glu-Glu, Gly-Gly, Gly-Gly- Gly, and Glu(Cys-Gly), was elucidated by means of UV/vis, circular dichroism, fluorescence, and 2D NMR spectroscopy in Tris-HCl buffer solution (pH 7.4) at 25 °C. The results obtained indicated that metallobridged bis(β-cyclodextrin)s 2 or 3 could significantly enhance the original molecular binding abilities of parent bis(β-cyclodextrin) 1 toward model substrates through the cooperative binding of two cyclodextrin moieties and the additional chelation effect supplied by the coordinated metal centers. It is interesting that hosts 2 and 3 displayed an entirely different fluorescence behavior upon complexation with guest oligopeptides. Among the guest peptides examined, 3 showed the highest complex formation constant of 68 200 M-1 for Glu-Glu, up to 510-fold as compared with 1 (135 M-1), while 1 gave excellent molecular selectivity for Glu(Cys-Gly)/Glu-Glu pair, up to 51-fold. The molecular binding ability and selectivity were discussed from the viewpoints of the induced-fit and multiple recognition mechanism between host and guest.
DOI: 10.1021/bc049870m
Rights: © 2004 American Chemical Society.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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