栄研スタッフによる解説論文集 資料　作成日　98/01/20
	Photonduced reactions-XXXVI ; Photonsesitized oxygenation of 3-hydroxyflavones as a nonenzymatic model for quercetinase
	著者: Matuura, T., Matsushima, H. and Nakashima, R.
	出典: Tetrahedron, 26, 435-443(1970)

要約

In connection with resemblance between photosensitized oxygenation and dioxygenase-catalysed enzymatic oxygenation, photosensitized oxygenation of 3-hydroxylavones 1a 1b, and lc was investigated. These compounds, on photooxygenation in the presence of rose bengal, gave corresponding depsides 2a, 2b, and 2c, carbon monoxide, and carbon dioxide. The formation of the depsides and carbon monoxide represents a chemical model for the eazymatic degradation of quercetin (1a) by quercetinase leading to the depside 2a. Possible mechanisms involving a hydroperoxide intermediate 5, which may be formed by the attack of singlet oxygen to 2a, are proposed. Photooxygenation of p-anisylglyoxylic acid to p-anisic acid and carbon dioxide and oxidative dimerization 3-hydroxyflavone (1c) to a dimer 10 are also described.

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