Journal of the Chemical Society. Perkin transactions I p. 67 - 74 (1996)
Update date:2022-08-04
Topics:
Boyd, Derek R.
Sharma, Narain D.
Kerley, Nuala A.
McMordie, R. Austin S.
Sheldrake, Gary N.
Williams, Paul
Dalton, Howard
Biotransformation of 1,2- and 1,4-dihydronaphthalene substrates, using growing cultures of Pseudomonas putida UV4, resulted in dioxygenase-catalysed benzylic monohydroxylation, cis-tetrahydro diol and cis-dihydro diol formation, trihydroxylation and dehydrogenation. The arene hydrates, (R)-1,2-dihydronaphthalen-1-ol 5 and (R)-1,4-dihydronaphthalen-1-ol 7, were isolated as enantiopure metabolites while 1,2-dihydronaphthalen-2-ol 8 was found in almost racemic form. The structure, enantiopurity and absolute stereochemistry of these arene hydrates of naphthalene were confirmed by chemical synthesis. Deuterium labelling studies, and the use of enantiomerically pure arene hydrates 5 and 7 as substrates, were used to establish the metabolic pathways for the formation of (1R,2S)-1,2-dihydronaphthalene-1,2-diols 2, from both 1,2-dihydronaphthalene 3 and 1,4-dihydronaphthalene 6 substrates.
View MoreJiangxi Lanqi Fine Chemical S&T Co., Ltd.
Contact:+86-21-64891143
Address:XinJiShan Industrial Area, Zhangshu City, JiangXi Province, China
website:http://www.arromax.com
Contact:+86-0512-62959601 skype:aimmezhang
Address:Suite 401, Bldg A3, 218 Xinghu St.Suzhou Industrial Park 215123, P.R. China
Wuxi Zuping Food Science And Technology Co.,LTD.
Contact:+86-510-87210822
Address:Guanlin town
Contact:+852-8198 2399
Address:9E, Leapont Industrial Building, 18-28 Wo Liu Hang Road, Shatin, New Territories, Hong Kong
Contact:+86-518-81061113
Address:No. 8 Lingzhou Road, Lianyungang, Jiangsu, China
Doi:10.1016/j.tetasy.2013.11.006
(2014)Doi:10.1002/ardp.200500162
(2006)Doi:10.1021/jo00187a003
(1984)Doi:10.1021/jo00187a020
(1984)Doi:10.1039/jr9630004566
(1963)Doi:10.1002/oms.1210190109
(1984)
