Coenzyme models. 50. Elavin activation by intramolecular acid catalysis at N(1) position.
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概要
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In order to assess the effect of intramolecular acid catalysis on the specific flavin reactivities, 3-methyl-10-(2-hydroxyphenyl)isoalloxazine (<B>1</B>(2OH)) and 3-methyl-10-(2-hydroxy-1-naphthyl)isoalloxazine (<B>2</B>(2OH)) were synthesized and the redox properties were compared with those of reference flavins such as 3-methyl-10-(2-methoxyphenyl)isoalloxazine (<B>1</B>(2OMe)) and 3-methyl-10-(2-methoxy-1-naphthyl)isoalloxazine (<B>2</B>(2OMe)). The p<I>K</I><SUB>a</SUB> values for <B>1</B>(2OH) and <B>2</B>(2OH) were determined to be 7.7 and 7.0, respectively, which were lower than that of 3-methyl-10-(4-hydroxyphenyl)isoalloxazine (<B>1</B>(4OH): p<I>K</I><SUB>a</SUB> 8.6). It is thus unlikely that 2′-OH and N(1) form a hydrogen bond at the initial state of the reaction (i.e., at the oxidized state). The X-ray crystallographic studies indicated that the phenyl ring makes an angle of 79.7° with the isoalloxazine ring and the 2′-OH group forms a hydrogen bond with methanol included in the crystal lattice. In acetonitrile at 30 °C 1-benzyl-1,4-dihydronicotinamide was not oxidized by <B>1</B>(2OMe), <B>1</B>(4OH), and <B>2</B>(2OMe). On the other hand, the oxidation took place with <B>1</B>(2OH) and <B>2</B>(2OH) which have an acidic OH group at the 2′-position of the 10-aryl substituent. The presence of the intramolecular acid catalysis suggests that 2′-OH and N(1) can interact at least at the transition state or at the final state of the reaction (i.e., at the reduced state). In general, the oxidized flavin adopts a "planar" structure which is sterically tense while the reduced flavin adopts a "bent" structure which is sterically relaxed. As the structure of the transition state is more or less similar to the reduced form, the hydrogen-bonding interaction could increase on going from the tense initial state to the relaxed transition state. This is a novel example for acid catalysis in flavin-mediated reactions.
- 公益社団法人 日本化学会の論文
著者
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Nakamura Hideki
Department of Cardiovascular Medicine, Abashiri Kohsei General Hospital
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Shinkai Seiji
Department Of Applied Chemistry Faculty Of Engineering Kyushu University
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Kasai Nobutami
Department Of Applied Biological Science Tokyo University Of Science
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Harada Shigeharu
Department Of Applied Biology Kyoto Institute Of Technology
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MANABE Osamu
Department of Applied Chemistry, Faculty of Engineering, Nagasaki University
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Yamaguchi Toshiro
Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University
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Kawanabe Sayuri
Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University
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Kawase Akito
Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University
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