東京工科大学 研究報告等

藤沢 章雄
所属  応用生物学部 応用生物学科
職種  教授
言語種別
英語
発行・発表の年月
2019年03月
形態種別
学術論文
査読
査読あり
標題
(2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic Acid as a Precursor of Parabanic Acid, the Singlet Oxygen-Specific Oxidation Product of Uric Acid.
執筆形態
共著
掲載誌名
Journal of Organic Chemistry
出版社・発行元
ACS puiblications
巻・号・頁
84(6),3552-3558
担当範囲
Corresponding Author
著者・共著者
Iida S, Yamamoto Y, Fujisawa A.
概要
Previously, we identified that parabanic acid (PA) and its hydrolysate, oxaluric acid (OUA), are the singlet oxygen-specific oxidation products of uric acid (UA). In this study, we investigated the PA formation mechanism by using HPLC and a time-of-flight mass spectrometry technique and identified unknown intermediates as (2,5-dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic acid (DIAA), dehydroallantoin, and 4-hydroxyallantoin (4-HAL). DIAA is the key to PA production, and its formation pathway was characterized using 18O2 and H218O. Two oxygen atoms were confirmed to be incorporated into DIAA: the 5-oxo- oxygen from singlet oxygen and the carboxylic oxygen from water. Isolated DIAA and 4-HAL gave PA stoichiometrically. A plausible reaction scheme in which two pathways branch out from DIAA is presented, and the potential for PA as an endogenous probe for biological formation of singlet oxygen is discussed.