波谱学杂志 ›› 2016, Vol. 33 ›› Issue (2): 281-287.doi: 10.11938/cjmr20160210

• 研究论文 • 上一篇    下一篇

胞苷盐酸盐的质子化位置研究

王强1, 李玉江1, 陶乐1, 郭晓河1, 董黎红1, 宋传君2, 常俊标2   

  1. 1. 河南省科学院 高新技术研究中心, 河南 郑州 450002;
    2. 郑州大学 化学与分子工程学院, 河南 郑州 450001
  • 收稿日期:2015-06-01 修回日期:2016-04-12 出版日期:2016-06-05 发布日期:2016-06-05
  • 通讯作者: 王强,电话:0371-65511776,E-mail:wangqiangno1@hotmail.com;常俊标,电话:0371-67781588,E-mail:changjunbiao@zzu.edu.cn. E-mail:wangqiangno1@hotmail.com;changjunbiao@zzu.edu.cn
  • 作者简介:王强(1977-),男,河南孟州人,博士,副研究员,药物化学专业.
  • 基金资助:

    国家自然科学基金资助项目(21172202);河南省重点科技攻关资助项目(152102210379).

Positions of Protonation in Cytidine Hydrochloride Revealed by NMR Spectroscopy

WANG Qiang1, LI Yu-jiang1, TAO Le1, GUO Xiao-he1, DONG Li-hong1, SONG Chuan-jun2, CHANG Jun-biao2   

  1. 1. High & New Technology Research Center of Henan Academy of Science, Zhengzhou 450002, China;
    2. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China
  • Received:2015-06-01 Revised:2016-04-12 Online:2016-06-05 Published:2016-06-05

摘要:

含有羧酸或碱性基团的药物成盐后具有药物水溶性提高、易于结晶纯化、稳定性增强等优点.胞苷类药物具有碱性中心,成盐后的质子化位置是在N-3还是NH2的研究还未见报道.X-射线单晶衍射因不能够对质子位置进行测定而无法对胞苷盐的质子化位置进行确定.该文利用核磁共振氢谱(1H NMR)、碳谱(13C NMR)研究了胞苷成盐前后的化学位移变化,推断出胞苷成盐位置在N-3而非NH2,此外胞嘧啶碱基C-4和NH2之间的键在成盐后具有部分双键性质.

关键词: 1H NMR, 13C NMR, 胞苷盐, 质子化位置

Abstract:

Compared to their parent forms of bases or acids, drugs in the form of salts have improved solubility, chemical stability, and capability for recrystallization. For the drug cytidine hydrochloride, whether the protonation position is at N-3 or NH2 remains unclear, and X-ray crystallography cannot provide this information. In this study, 1H and 13C NMR spectroscopy was used to study the exact protonation position in cytidine hydrochloride. It was shown clearly by chemical shift changes that the protonation position is at N-3 rather than NH2. It was further confirmed that the chemical bond between C-4 and NH2 in cytidine salts has double bond-like properties.

Key words: 1H NMR, 13C NMR, cytidine hydrochloride, protonation position

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