高等学校化学学报

高等学校化学学报 ›› 1993, Vol. 14 ›› Issue (6): 795.

• 研究论文 • 上一篇    下一篇

腺嘌呤核苷3',5'-环烷基膦酸类似物的立体化学研究

杨宪斌, 陈欣, 王春光, 张礼和   

  1. 北京医科大学天然药物及仿生药物国家重点实验室, 北京 100083
  • 收稿日期:1992-09-25 修回日期:1993-02-18 出版日期:1993-06-24 发布日期:1993-06-24
  • 通讯作者: 张礼和
  • 基金资助:

    国家自然科学基金

Studies on Stereochemistry of Adenosine 3', 5'-Cycloalkylphosphonate

YANG Xian-Bin, CHEN Xin, WANG Chun-Guang, ZHANG Li-He   

  1. National Research Labaratorits of Natural and Biominetic Drngs.Reijing Medical University, Beijing, 100083
  • Received:1992-09-25 Revised:1993-02-18 Online:1993-06-24 Published:1993-06-24

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摘要： 利用一维NOE差谱技术确定了2'-对甲苯磺酰基-腺嘌呤核苷3',5'-环甲基和环正丁基膦酸类似物磷原子的绝对构型。二维(J,δ)分解谱分析表明,它们的膦酸环的构象为椅式和扭船式并存,以椅式为主,扭船式构象的分数随溶剂极性的增加或随温度的升高而增加;它们的碱性水解开环产物以磷原子连在5'-OH为主。

关键词: 腺嘌呤核苷3', 5'-环烷基膦酸, 立体化学, 二维核磁共振

Abstract: The configuration of phosphorus in2'-toluenesulfonyl-adenosine-;3',5,'-cydlc methyl phos-phonate (Ⅰ) and cyciic-R-butylphosphonate (Ⅰ) were determined by using NOEtechnique, The data indicate that they are Sforms.The conformations of cyeloalkylphosphonate moieties were identified by two dimension HOM2 DJspectroscopy which shows that there exists an equilibrium between chair and twist forms in the solution.The population of chair conformation is higher than that of twist conformation and the ratio increased with increase of the polarity of solvent and temperature.The main hydrolysates of Ⅰ and Ⅱ in NH4OHand CH3OHare derivatives of nucleoside 5'-alkylphosphonate.

Key words: Adenosine 3',5'-cycloalkylphosphonate, Stereochemistry, Two-demension NMR

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