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Facile Photo-Oxidation of Alcohols by a Flavin with a Metal-Chelation Site


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タイトル: Facile Photo-Oxidation of Alcohols by a Flavin with a Metal-Chelation Site
著者: Shinkai, Seiji / Nakao, Hideki / Ueda, Kaori / Manabe, Osamu
発行日: 1987年 7月
出版者: 長崎大学工学部 / Faculty of Engineering, Nagasaki University
引用: 長崎大学工学部研究報告, 17(29), pp.184-189; 1987
抄録: A new flavin molecule with a metal-chelation site has been applied to photo-oxidation of alcohols: it is 2, 4, 7-trimethyl-10-benzylquino [8, 7-g] pteridine-9, 11 (7H, 10H) -dione (1) which has both an isoalloxazine structure and a phenathroline-like structure within a molecule. In contrast to conventional flavins which do not exhibit any measurable affinity toward redox-inactive transition metal ions, 1 formed stable complexes with most heavy metal ions in acetonitrile probably by means of a flavin → metal charge transfer. Photooxidation of alcohols by 1 was efficiently accelerated in the presence of Mg(II) and Zn(II), the k1 (pseudo-first-order rate constant) being greater by 5.1-7l fold than those in the absence of metal ions. Such a marked rate increase was not observed for 3-methyl-10-ethylisoalloxazine used as a reference flavin. The aerobic photo-oxidation of benzyl alcohol by the 1・Zn(II) complex served as a light-mediated recycle oxidation catalyst. These results indicate that the flavin with a metal-chelation site is not only useful synthetically as a recycle-type oxidation catalyst but also capable of mimicking the flavin-metal interactions important in metalloflavoproteins.
URI: http://hdl.handle.net/10069/24246
ISSN: 02860902
資料タイプ: Departmental Bulletin Paper
原稿種類: publisher
出現コレクション:第17巻 第29号

引用URI : http://hdl.handle.net/10069/24246

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