Journal of the Chemical Society. Perkin transactions I p. 1153 - 1156 (1989)
Update date:2022-09-26
Topics:
Ienaga, Kazuharu
Nakamura, Ko
Ishii, Akira
Taga, Tooru
Miwa, Yoshihisa
Yoneda, Fumio
The metabolism of 1-methylhydantoin (2) is described.The major and general metabolic route in mammals, represented by formulae (2) to (7), includes two consecutive stepwise oxidations giving 5-hydroxy-1-methylhydantoin (3) and thence 1-methylparabanic acid (4).Since the first oxidation proved to be stereoselective, the step was thought to be enzymatic.Although enantiomeric products (3a) and (3b) (ca. 3:1) could not be separated directly, the mixture was converted into (S)- and (R)-5-(N-benzyloxycarbonyl-L-prolyloxy)-1-methylhydantoins (13a) and (13b) which proved separable and were identified by X-ray analysis of the (R)-diastereoisomer.The regioselective ring-fission of the second product (4) into the methyloxaluric acid (5) is discussed.Two minor oxidative routes from the substrate (2) into sarcosine (9) and parabanic acid (10) were also shown to exist.
View MoreNanjing Spring & Autumn Biological Engineering Co., Ltd.
Contact:86-180510-83338
Address:Suite# 210, No. 1 BuildingNanjing Agricultural Biotechnology High-tech Entrepreneurship Center, No. 4 Tongwei Road, Xuanwu District, Nanjing,China
Rudong Zhenfeng Yiyang Chemical Co., Ltd.
Contact:0513-84573047
Address:South Fengli Town, Rudong County, Jiangsu Province, China
Wuxi D-Stone International Co., Ltd.
Contact:+86-510-82740567
Address:21F Hengtong Int'l Centre, 215Zhongshan Road, Wuxi, Jiangsu,China
Contact:86-25-58619180
Address:Nanjing High-Tech Zone 10 Xinghuo Road Pukou District Nanjing, Jiangsu 210061 The People's Republic of China
website:http://www.maisonchem.com.cn
Contact:0086-311-83833777
Address:Leitou industrial district, xinji, shijiazhuang city, hebei province,
Doi:10.1002/tcr.201402084
(2015)Doi:10.1016/j.tet.2011.07.044
(2011)Doi:10.1016/j.bmcl.2016.10.034
(2016)Doi:10.1039/b917169j
(2010)Doi:10.1016/j.ejmech.2009.12.021
(2010)Doi:10.1055/s-1988-27647
(1988)
