Beilstein Journal of Organic Chemistry p. 1643 - 1647 (2011)
Update date:2022-09-26
Topics:
Klein, Christian
Huettel, Wolfgang
The enzymatic synthesis of tertiary alcohols by the stereospecific oxidation of tertiary alkyl centers is a most-straightforward but challenging approach, since these positions are sterically hindered. In contrast to P450-monooxygenases, there is little known about the potential of non-heme iron(II) oxygenases to catalyze such reactions. We have studied the hydroxylation of trans-3-methyl-Lproline with the a-ketoglutarate (α-KG) dependent oxygenases, cis-3-proline hydroxylase type II and cis-4-proline hydroxylase (cis-P3H-II and cis-P4H). With cis-P3H-II, the tertiary alcohol product (3R)-3-hydroxy-3-methyl-L-proline was obtained exclusively but in reduced yield (~7%) compared to the native substrate L-proline. For cis-P4H, a complete shift in regioselectivity from C-4 to C-3 was observed so that the same product as with cis-P3H-II was obtained. Moreover, the yields were at least as good as in control reactions with L-proline (~110% relative yield). This result demonstrates a remarkable potential of non-heme iron(II) oxygenases to oxidize substrates selectively at sterically hindered positions. 10.3762/bjoc.7.193.
View MoreSuzhou CarbonWell Pharma-Tech Co., Ltd
Contact:Tel: + 86 (0)512-8898-1216; + 86-18606258602
Address:2358 Changan Road, Wujiang Scientific Innovation Park, Wujiang, Jiangsu Province, P. R. China 215200
chengdu firsterchem Pharmaceutical Co., Ltd.
Contact:028-66825849
Address:chengdu
Jinan Chenghuishuangda Chemical CO.,Ltd
website:http://www.jnchsd.com
Contact:+86-531-58897082
Address:No.2350, Kaituo Road, High-tech Development District, Jinan City, Shandong, China
Shouguang Nuomeng Chemical Co., Ltd.
Contact:+86-536-5119508/18363669993
Address:Hou Zhen Industrial Park, Shouguang, Shandong, China
Rudong Zhenfeng Yiyang Chemical Co., Ltd.
Contact:0513-84573047
Address:South Fengli Town, Rudong County, Jiangsu Province, China
Doi:10.1002/(SICI)1099-0690(199907)1999:7<1671::AID-EJOC1671>3.0.CO;2-Z
(1999)Doi:10.1021/jo00030a014
(1992)Doi:10.1016/j.tet.2012.05.063
(2012)Doi:10.1021/jo00035a007
(1992)Doi:10.1016/j.tet.2012.05.041
(2012)Doi:10.1021/ja3026714
(2012)