Nitrobenzoxadiazole-labelled polyisoprenoid alcohols
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We have prepared, isolated, and characterized a series of nitrobenzoxadiazole labelled polyisoprenoid alcohols. The coupling reaction employed was a dicyclohexylcarbodiimide mediated condensation between a carboxylic acid derivative of nitrobenzoxadiazole and the polyisoprenoid alcohols citronellol, solanesol, and dolichol. Upon exposure to visible light, a self-sensitized singlet oxygen "ene" reaction oxidized double bonds in the isoprene moiety. The rate of oxidation is greatly reduced in solvents where singlet oxygen is short-lived. Key words: nitrobenzoxadiazole, isoprenoid, dolichol, citronellol, solanesol, fluorescence labelling, singlet oxygen, ene reaction.
2008 ◽
Vol 78
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pp. 1127-1138
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1985 ◽
Vol 6
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pp. 171-178
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2014 ◽
Vol 147
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pp. 121-128
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1984 ◽
Vol 17
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pp. 441-446
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2003 ◽
Vol 217
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pp. 87-97
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