Molecular recognition of aliphatic oligopeptides by aromatic diamine-bridged bis(beta-cyclodextrin)

作者：Zhao Yan^*; Gu Juan; Yang Yong Cun; Shi Hao; Zhu Hong You; Huang Rong; Jing Bi

来源：Research on Chemical Intermediates, 2009, 35(5): 597-605.

DOI：10.1007/s11164-009-0064-2

• Bridged bis(beta-cyclodextrin)s
• Aliphatic oligopeptides
• Fluorescence spectroscopy
• Molecular recognition
• Inclusion complexation

Binding behavior of 4,4'-diaminodiphenyl ether-bridged-bis (6-amino-6-deoxy-beta-cyclodextrin) 1 with the aliphatic oligopeptides, i.e., Leu-Gly, Gly-Leu, Glu-Glu, Met-Met, Gly-Gly, Gly-Gly-Gly, and Gly-Pro was investigated at 25A degrees C in phosphate buffer (pH 7.20) by fluorescence and 2-D NMR spectroscopy. Owing to the cooperative "cyclodextrin-guest-cyclodextrin" sandwich binding mode, bis(beta-cyclodextrin) 1 not only afford high binding constants of up to 10(3)-10(4) M(-1) for guest oligopeptides, but can also recognize the size and hydrophobicity of oligopeptides. As a result of multiple recognition mechanisms, bis(beta-cyclodextrin) 1 gives high length-selectivity up to 5.8 for the Gly-Gly-Gly/Gly-Gly pair and sequence-selectivity up to 2.8 for the Gly-Leu/Leu-Gly pair, respectively. The molecular binding ability and selectivity are discussed from the viewpoints of induced-fit and multiple recognition between host and guest.

• 出版日期2009-5
• 单位云南师范大学; 云南大学