有机化学 ›› 2017, Vol. 37 ›› Issue (7): 1814-1823.DOI: 10.6023/cjoc201610045 上一篇    下一篇

研究论文

具有叶绿素碳架的二氢卟吩醛的合成及其与蛋白质的结合作用

姜齐永a, 张珠a, 刘洋b, 姚楠楠b, 王进军a,b   

  1. a. 烟台大学文经学院 食品与生物工程系 烟台 264005;
    b. 烟台大学化学化工学院 烟台 264005
  • 收稿日期:2016-10-31 修回日期:2017-01-16 发布日期:2017-03-03
  • 通讯作者: 王进军 E-mail:wjj1955@163.com
  • 基金资助:

    国家自然科学基金(No.21272048)和山东省高校科技计划(No.J15LC51)资助项目.

Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein

Jiang Qiyonga, Zhang Zhua, Liu Yangb, Yao Nannanb, Wang Jinjuna,b   

  1. a. Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai 264005;
    b. College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005
  • Received:2016-10-31 Revised:2017-01-16 Published:2017-03-03
  • Contact: 10.6023/cjoc201610045 E-mail:wjj1955@163.com
  • Supported by:

    Project supported by the National Natural Science Foundations of China (No.21272048) and the University Science and Technology Plan Projects of Shandong Province (No.J15LC51).

以脱镁叶绿酸-a(b)甲酯为起始原料,经外接环修饰和色基金属化形成不同的叶绿素降解产物,再通过Vilsmeier酰基化和Blanc羟甲基化反应,在20-位上引进了新的官能基团.以四氧化锇、硝酸铊和空气为氧化剂,对二氢卟吩周环上的活性结构进行氧化,分别在二氢卟吩周环上的3-,7-和12-位以及外接环上引进了甲酰基和甲酰甲基,合成了一系列未见报道的叶绿素类二氢卟吩醛衍生物,其化学结构均经UV,IR,1H NMR及元素分析予以证实;同时也讨论了叶绿素类二氢卟吩醛基化的反应机理,并对新化合物与牛血清白蛋白的结合作用进行了研究.

关键词: 叶绿素, 二氢卟吩, 牛血清白蛋白, 化学修饰, 荧光淬灭

Pyropheophorbide-a (b) methyl esters were used as starting materials to form different chlorophyll degradation products by the modification of the exocyclic ring and the metallization of the chromophore. The new functional groups were introduced at 20-position via the Vilsmeier acylation and the Blanc hydroxymethylation. The active structures of chlorin peripheries were oxidized using osmium tetroxide, thaillum nitrate and air as oxidizing agent to introduce the formyl group and the formylmethyl group at 3-, 7-or 12-postion and on the exocyclic ring, respectively. A series of unreported chlorin aldehydes related to chlorophyll were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra. The reaction mechanisms on the hydroformylation for the chlorophyllous chlorins were discussed and the interactions of new compounds with bovine serum albumins were researched.

Key words: chlorophyll, chlorin, bovine serum albumins, chemical modification, florescence quenching