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

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (08): 1192-1200. Previous Articles Next Articles

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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

(Science and Engineering College of Chemistry and Biology, Yantai University, Yantai 264005)

Received:2009-05-12 Revised:2010-01-06 Published:2010-03-17

Abstract

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)

Cite this article

WANG Jin-Jun, ZHANG Peng, WANG Peng, CHEN Guan-Long, LI Fu-Guo. Synthesis of Chorin Alcohol Derivatives by Chemical Modifications for Chlorophyll-a and Its Degradation Products[J]. Chin. J. Org. Chem., 2010, 30(08): 1192-1200.

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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

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

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