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化学学报
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化学学报 ›› 1989, Vol. 47 ›› Issue (2): 194-198. 上一篇    下一篇

研究论文

荧光黄素敏化胆固醇的单重态氧反应

江致勤;曾代迅;刘有成   

  1. 同济大学测试中心;兰州大学应用有机化学国家重点实验室
  • 发布日期:1989-02-15

Singlet oxygen photooxidation of cholesterol sensitized by lumiflavin

JIANG ZHIQIN;ZENG DAIXUN;LIU YOUCHENG   

  • Published:1989-02-15

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566

被引次数

5

本文合成了无长链的荧光黄素, 在不同溶剂中研究了荧光黄素敏化胆固醇的光氧化反应, 实验观察到, 荧光黄素敏化胆固醇在乙腈, 吡啶和苯中光氧化, 形成胆固醇的5或7位过氧化氢和胆甾烯酮, 这些胆固醇氢过氧化基可用三苯基膦将其还原成相应的醇:6-胆甾烯-3β, 5α-二醇, 5-胆甾醇-3β, 7α-二醇, 5-胆甾烯-3β-醇-7酮.

关键词: 氧化, 光氧化, 胆甾醇, 甾醇, 敏化, 甾酮, 单线态氧, 黄素蛋白, 荧光黄素

The sensitized photooxidn. of cholesterol (I) was carried out in several solvents and gave cholest-6-en-3b,5a-diol, cholest-5-en-3b,7a-diol and -3b,7b-diol and cholest-5-en-3b-ol-7-one (II). The product distribution depends on sensitizer and solvent used. In particular, a new product II is formed in the lumiflavin (LF)-sensitized photooxidn. of I. The rates of the photooxidns. in polar solvents are considerably faster than that in nonpolar solvents which are favorable to the formation of IV. Based on the results, it is proposed that the photooxidn. proceeds mainly via a singlet oxygen (1O2) pathway.

Key words: OXIDATION, PHOTOOXIDATION, CHOLESTEROL, STEROL, SENSITIZATION, STERONE, SINGLET OXYGEN, FLAVOPROTEIN, LUMIFLAVIN

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