Beilstein J. Org. Chem.2015,11, 392–402, doi:10.3762/bjoc.11.45
considered as analogical to the Gif-system. In this approach, hydrogen peroxide was exchanged for a process of dioxygen activation with electrochemically generated [FeII(PA)3OH2]− ions. With the system, stereoselective allylichydroxylation of cholesteryl acetate was carried out [35]. The H-shaped one
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Graphical Abstract
Figure 1:
Preferential sites of cholesterol electrooxidation.
Beilstein J. Org. Chem.2014,10, 1347–1353, doi:10.3762/bjoc.10.137
. Regioselective oxidation of parental alkenes is a challenging task for chemical catalysts and requires several steps including protection and deprotection. Many cytochrome P450 enzymes are known to catalyse selective allylichydroxylation under mild conditions. Here, we describe CYP154E1 from Thermobifida fusca
-box for allylichydroxylation in synthetic chemistry.
Keywords: allylichydroxylation; cytochrome P450; natural products; protein engineering; regiochemistry; terpenoids; Introduction
Direct allylichydroxylation yielding highly valuable allylic alcohols has been recognised for a while as one of the
hydroxylation reactions leading to synthetically relevant intermediates [5][6][7][8][9][10][11]. In addition to chemical catalysts a range of enzymes has been studied for selective allylichydroxylation of alkenes [12][13]. Among biosynthetic routes selective allylichydroxylation of monoterpene olefines to
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Graphical Abstract
Figure 1:
Immediate heme surroundings shown for the nearest relative of CYP154E1 with available crystal struc...