Kinetic characterisation of the FAD dependent monooxygenase TropB and investigation of its biotransformation potential

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Abood, Amira; Al-Fahad, Ahmed; Scott, Alan; Hosny, Alaa El-Dein M. S.; Hashem, Amal M.; Fattah, Azza M. A.; Race, Paul R.; Simpson, Thomas J.; Cox, Russell J.: Kinetic characterisation of the FAD dependent monooxygenase TropB and investigation of its biotransformation potential. In: Rsc Advances 5 (2015), Nr. 62, S. 49987-49995. DOI:

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Achieving regio-specific hydroxylation of aromatic compounds remains a major challenge in synthetic chemistry. By contrast, this transformation is readily accomplished in nature through the action of FAD-dependant monooxygenase enzymes. Here, we report the kinetic characterisation of one such enzyme, TropB, from the stipitatic acid biosynthetic pathway. Analogues of the TropB natural substrate, 3-methyl-orcinaldehyde, were synthesised and used to examine the substrate selectivity of this enzyme. TropB displays broad substrate tolerance, for instance accepting single-ring aromatic substrates containing a range of C-1 substituents with varying electronic and steric properties. These include nitro, nitrosyl, alkyl, and aryl keto groups. Bicyclic substrates, however, were rejected by TropB. Additionally, C-5 substituents on single-ring aromatic substrates were not tolerated whereas the presence of a 6-methyl group was found to be important for substrate binding. Docking studies were employed to investigate and understand the broad substrate selectivity of TropB and identifies the key structural elements of its substrates. Our work has shown that TropB is an attractive target for biocatalyst engineering and industrial aromatic hydroxylation.
License of this version: CC BY 3.0 Unported
Document Type: article
Publishing status: publishedVersion
Issue Date: 2015-05-29
Appears in Collections:Naturwissenschaftliche Fakultät

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1 image of flag of Germany Germany 128 68.82%
2 image of flag of United States United States 31 16.67%
3 image of flag of Ukraine Ukraine 4 2.15%
4 image of flag of Russian Federation Russian Federation 4 2.15%
5 image of flag of Korea, Republic of Korea, Republic of 3 1.61%
6 image of flag of China China 3 1.61%
7 image of flag of Canada Canada 3 1.61%
8 image of flag of United Kingdom United Kingdom 2 1.08%
9 image of flag of Hungary Hungary 1 0.54%
10 image of flag of Czech Republic Czech Republic 1 0.54%
    other countries 6 3.23%

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