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化学学报
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化学学报 ›› 2006, Vol. 64 ›› Issue (1): 22-26. 上一篇    下一篇

研究论文

分子亲脂-亲水性的量子化学描述II. 氨基酸侧链的亲水指标和亲脂指标

杜奇石*,1,2，刘朋军1，孙浩2，李大鹏2，谢军民2   

  1. (1海南师范大学化学系 海口 571158 )
    (2天津师范大学生物信息与药物开发研究所 天津 300074)
  • 投稿日期:2005-05-21 修回日期:2005-09-20 发布日期:2006-01-14
  • 通讯作者: 杜奇石

Quantum Chemical Description for Molecular Lipophilicity and Hydrophilicity: II. Lipophilic Indices and Hydrophilic Indices of Aminoacid Side Chains

DU Qi-Shi*,1,2, LIU Peng-Jun1, SUN Hao2, LI Da-Peng2, XIE Jun-Min2   

  1. (1 Department of Chemistry, Hainan Normal University, Haikou 571158)
    (2 Institute of Bioinformatics and Drug Discovery, Tianjin Normal University, Tianjin 300074)
  • Received:2005-05-21 Revised:2005-09-20 Published:2006-01-14
  • Contact: DU Qi-Shi

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在启发式亲脂势HMLP (heuristic molecular lipophilicity potential)的基础上提出了分子、分子片段和原子的亲水指标和亲脂指标. 计算出了20个天然氨基酸侧链的亲水、亲脂指标和亲水、亲脂表面积, 并用线性自由能函数表达氨基酸侧链的溶剂化自由能, ΔGsol,iθ＝b0＋b1Li＋b2Hi＋b3Si＋＋b4Si－. . 应用线性自由能函数和氨基酸侧链的亲水和亲脂指标, 计算了20个氨基酸残基的3种相转移自由能(蒸气-水、蒸气-正辛醇、正辛醇-水)和正辛醇-水分配系数logPow, 取得了与实验值高度一致的良好效果. HMLP的亲水和亲脂指标是HMLP的指标化, 扩展了这一方法的使用范围. 氨基酸侧链的亲水、亲脂指标和线性自由能函数有望用于生物大分子受体与配体的结合自由能的估算、蛋白质的结构与功能、蛋白-蛋白相互作用和识别的研究.

关键词: 启发式亲脂势(HMLP), 亲脂指标, 蛋白质, 氨基酸, 生物信息学

Heuristic molecular lipophilicity potential (HMLP) was applied to the study of lipophilicity and hydrophilicity of 20 natural aminoacid side chains. The HMLP parameters, surface area Ai, lipophilic indices Li and hydrophilic indices Hi of aminoacid side chains were derived from lipophilicity potential L(r). The parameters were correlated with the experimental data of phase transfer free energies of vapor-to-water, vapor-to-octanol, and octanol-to-water through a linear free energy equation ΔGsol,iθ＝b0＋b1Li＋b2Hi＋b3Si＋＋b4Si－. For all above 3 types of transfer free energies between different medium phases, the HMLP parameters of 20 aminoacid side chains provided good descriptions. HMLP is an ab initio quantum chemical approach and a structure-based technique. Except for atomic van der Waals radii, there was no other empirical parameter used. The computational results of HMLP have clear physical and chemical meaning and could provide useful lipophilic and hydrophilic parameters for the studies of proteins and peptides.

Key words: heuristic molecular lipophilicity potential (HMLP), lipophilicity index, protein, aminoacid, biological informatics