Structural and Energetic Basis of Carbohydrate-Aromatic Packing Interactions in Proteins

被引:82
作者
Chen, Wentao [1 ,2 ,3 ]
Enck, Sebastian [2 ,3 ]
Price, Joshua L. [1 ,2 ]
Powers, David L. [4 ]
Powers, Evan T. [2 ,3 ]
Wong, Chi-Huey [2 ,3 ,5 ]
Dyson, H. Jane [6 ]
Kelly, Jeffery W. [1 ,2 ,3 ]
机构
[1] Scripps Res Inst, Dept Mol & Expt Med, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[4] Clarkson Univ, Dept Math, Potsdam, NY 13676 USA
[5] Acad Sinica, Genom Res Ctr, Taipei 115, Taiwan
[6] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
基金
美国国家卫生研究院;
关键词
HEAT-CAPACITY CHANGES; MOLECULAR RECOGNITION; PI INTERACTIONS; GLYCOSYLATION; STABILITY; BINDING; NMR; STABILIZATION; SURFACE; LECTIN;
D O I
10.1021/ja4040472
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Carbohydrate aromatic interactions Mediate many biological processes. However, the stnicture-energy relationships underpinning direct carbohydrate-aromatic packing interactions in aqueous solution have been,difficult to assess experimentally and remain elusive. Here, we determine the structures and folding energetics of chemically synthesized glycoproteins to quantify the contributions of the hydrophobic effect and CH-pi interactions to carbohydrate-aromatic packing interactions in proteins. We find that the hydrophobic effect contributes significantly to protein-carbohydrate interactions. Interactions between carbohydrates and aromatic amino acid side chains, however, are supplemented by CH-pi interactions. The strengths of experimentally determined carbohydrate CH-pi interactions do not correlate with the electrostatic properties of the involved aromatic residues, suggesting that the electrostatic component of CH-pi interactions in aqueous solution is small. Thus, tight binding of carbohydrates and aromatic residues is driven by the hydrophobic effect and CH-pi interactions featuring a dominating dispersive component.
引用
收藏
页码:9877 / 9884
页数:8
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