Conformational Analysis of Trandolapril in Solution by NMR

doi:10.3969/j.issn.0251-0790.2012.01.026

Chem. J. Chinese Universities ›› 2012, Vol. 33 ›› Issue (01): 153.doi: 10.3969/j.issn.0251-0790.2012.01.026

• Physical Chemistry • Previous Articles Next Articles

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. 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

Abstract

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

CLC Number:

O641
O657

TrendMD:

SHEN Li, JIANG Jin-Liang, YU Yi-Hua, WU Yan-Bo, SUN Xiu-Yan, GU Qian-Qun. Conformational Analysis of Trandolapril in Solution by NMR[J]. Chem. J. Chinese Universities, 2012, 33(01): 153.

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Conformational Analysis of Trandolapril in Solution by NMR

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