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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (08): 1192-1200. 上一篇    下一篇

研究论文

叶绿素-a及其降解产物的化学修饰与二氢卟吩醇类衍生物的合成

王进军*，张朋，王朋，陈冠龙，李付国   

  1. (1烟台大学化学生物理工学院 烟台 264005)
  • 收稿日期:2009-05-12 修回日期:2010-01-06 发布日期:2010-03-17
  • 通讯作者: 王进军 E-mail:wjj1955@163.com
  • 基金资助:

    山东省自然科学基资助项目(No.Y2008B49); 山东省教育厅科技计划资助项目(No.J05D05); 胶体与界面化学教育部重点实验室（山东大学）开放课题资助项目(No.200711).;中科院.长江计划

Synthesis of Chorin Alcohol Derivatives by Chemical Modifications for Chlorophyll-a and Its Degradation Products

WANG Jin-Jun, ZHANG Peng, WANG Peng, CHEN Guan-Long, LI Fu-Guo   

  1. (Science and Engineering College of Chemistry and Biology, Yantai University, Yantai 264005)
  • Received:2009-05-12 Revised:2010-01-06 Published:2010-03-17

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以叶绿素-a为基本原料, 在酸性条件下一锅法完成脱金属、酯交换、空气氧化和重排反应, 以不同的产率生成多种叶绿素-a的降解和氧化产物. 通过加成、氧化和还原反应, 对其主要降解产物脱镁叶绿酸-a甲酯和焦脱镁叶绿酸-a甲酯的3-位乙烯基和E-环羰基实施化学修饰, 在叶绿素-a基本碳架的不同位置上引进羟基, 完成9种未见报道的二氢卟吩醇类衍生物的合成. 所合成的新化合物均经UV, IR, 1H NMR及元素分析证明其结构.

关键词: 叶绿素-a, 氧化降解, 化学修饰, 二氢卟吩醇, 光动力治疗(PDT)

The demetal, ester exchange, allomerization and rearrangement reactions were accomplished by one pot method using chlorophyll-a as a basic material to yield various degraded and oxidized chlorin de-rivatives in different yields. The chemical modification for the vinyl group on 3-position and carbonyl group on the E-ring of methyl pheophorbide-a and methyl pyropheophorbide-a, as primary degraded products were carried out by addition, oxidation and reduction. The hydroxyl groups were introduced into the different positions on the basic skeleton of chlorophyll-a derivatives to complete the synthesis of 9 different new chlorin alcohols. The structures of all new compounds were characterized by elemental analysis, UV, IR and 1H NMR techniques.

Key words: chlorophyll-a, oxydegradation, chemical modification, chlorin alcohol, photodynamic therapy (PDT)