高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (01): 153.doi: 10.3969/j.issn.0251-0790.2012.01.026

• 物理化学 • 上一篇    下一篇

群多普利溶液构象的NMR研究

沈莉1, 姜金良2, 余亦华3, 吴艳波4, 孙秀燕5, 顾谦群1   

  1. 1. 中国海洋大学医药学院, 教育部海洋药物重点实验室, 青岛 266003;
    2. 中国科学院研究生院化学与化学工程学院, 北京 100049;
    3. 华东师范大学物理系, 上海市磁共振重点实验室, 上海 200062;
    4. 山西大学分子科学研究所, 太原 030006;
    5. 烟台大学药学院, 烟台 264005
  • 收稿日期:2011-03-25 出版日期:2012-01-10 发布日期:2011-12-20
  • 通讯作者: 顾谦群,女,教授,博士生导师,主要从事海洋天然产物研究.E-mail:guqianq@ouc.edu.cn E-mail:guqianq@ouc.edu.cn
  • 基金资助:

    国家自然科学基金(批准号: 20804016, 20874029)资助.

Conformational Analysis of Trandolapril in Solution by NMR

SHEN Li1, JIANG Jin-Liang2, YU Yi-Hua3, WU Yan-Bo4, SUN Xiu-Yan5, GU Qian-Qun1   

  1. 1. Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China;
    2. College of Chemistry and Chemical Engineering, Graduate University of Chinese Academy of Sciences, Beijing 100049, China;
    3. Shanghai Key Laboratory of Magnetic Resonance, Department of Physics, East China Normal University, Shanghai 200062, China;
    4. Institute of Molecular Science, Shanxi University, Taiyuan 030006, China;
    5. School of Pharmacy, Yantai University, Yantai 264005, China
  • Received:2011-03-25 Online:2012-01-10 Published:2011-12-20

摘要: 采用1D和2D NMR技术对血管紧张素转化酶抑制剂群多普利在CDCl3溶液中存在的两种构象进行了结构解析, 并结合分子动力学和密度泛函理论方法对其进行了结构的几何优化和能量计算. 结果表明, 群多普利因分子中酰胺键的旋转而形成反式构象A和顺式构象B, 两种构象的能量差为6.35 kJ/mol, 且顺式构象为该药物的优势构象.

关键词: 群多普利, 核磁共振, 构象, 优势构象

Abstract: Trandolapril, a potent inhibitor of angiotensin converting enzyme, was studied by nuclear magnetic resonance(NMR) spectroscopy. It was found that trandolapril had two conformations in CDCl3, and conformer A could converted gradually into conformer B at room temperature. The two conformations of trandolapril were elucidated by NMR spectroscopy and in combination with structural simulation based on density function theory(DFT). The results show that the two conformers of trandolapril interchange via rotation about the amide bond, and the conformer B(cis) is the preferred conformation. The energy difference of two conformers is 6.35 kJ/mol.

Key words: Trandolapril, Nuclear magnetic resonance, Conformation, Preferred conformation

中图分类号: 

TrendMD: