Tetrahedron p. 6199 - 6204 (2018)
Update date:2022-08-11
Topics:
Migglautsch, Anna K.
Willim, Melissa
Schweda, Bettina
Glieder, Anton
Breinbauer, Rolf
Winkler, Margit
Microbial cytochrome P450 enzymes (CYPs) are able to mimic the metabolism of human CYPs. One challenge is to identify the respective drug metabolites and to compare substrate specificities to those of the human enzymes. In this study, a class VIII self-sufficient CYP from Aspergillus fumigatus (CYP505X) and variants of this enzyme were heterologously expressed in E. coli. The substrate scope of the variants was determined using active pharmaceutical ingredients (APIs) and (hetero)cyclic compounds. Capsaicin – the active compound in chili peppers – was oxidized most efficiently (4.36 μM/min) in a whole cell mediated biotransformation. The products were isolated, purified and their structures elucidated by 1D and 2D NMR. The two major metabolites showed modifications on the lipophilic side chain. Specifically, capsaicin was hydroxylated at position 8 to give (E)-8-hydroxy-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide and epoxidized at the double bond to give N-(4-hydroxy-3-methoxybenzyl)-5-(3-isopropyloxiran-2-yl)-pentanamide.
View MoreBAODING SINO-CHEM INDUSTRY CO.,LTD
Contact:0312-5956088
Address:NO.8 FUXING ROAD,CHINA
Lyrin Industrial Corporation Limited
Contact:86-731-82571800
Address:Rm 2408,Asia Economy International Building,Shaoshan Road South,Yuhua District,Changsha,Hunan,China
shijiazhuang baisheng chem co.; ltd
Contact:86-0311-80790826
Address:shijiazhuang hebei
Shijiazhuang Haitian Amino Acid Co., Ltd.
Contact:+86-311-88908111
Address:Shijiazhuang Hebei province,China
A.M FOOD CHEMICAL CO., LIMITED
Contact:86-531-87100375
Address:20Floor,Bblock,1Building,pharma-valley,Jinan,China
Doi:10.1002/hlca.19320150141
(1932)Doi:10.1002/anie.201204259
(2012)Doi:10.1039/c6ra10527k
(2016)Doi:10.1039/b103350f
(2001)Doi:10.1021/ja909111p
(2010)Doi:10.1016/j.bmc.2016.07.056
(2016)