Benzylic hydroxylation of aromatic compounds by P450 BM3
Literature Information
Katharina Neufeld, Jan Marienhagen, Ulrich Schwaneberg
Cytochrome P450 BM3 monooxygenase from Bacillus megaterium and its variants are promising catalysts for organic synthesis. Aiming at the identification of variants for selective hydroxylation of functionalised aromatic compounds, the double mutant F87A L188C showed remarkably improved catalytic activity towards a set of tested toluene derivatives. The apparent catalytic efficiency of this variant towards the model substrate methyl 2-methoxy-3-methylbenzoate was 63.6 s−1 M−1, which is 535-fold higher compared to that of wild-type BM3. Furthermore, the double mutant selectively catalysed the benzylic hydroxylation of numerous toluene derivatives, especially in the presence of carbonyl- or carboxyl-functions that are directly attached to the aromatic ring. Preparative scale conversion resulted in efficient production of methyl 3-(hydroxymethyl)-2-methoxybenzoate (73% yield) which proved that F87A L188C is a suitable, efficient and sustainable catalyst for the introduction of benzylic hydroxyl groups in general.
Recommended Journals

Journal of Physics and Chemistry of Solids

Proceedings of the National Academy of Sciences of the United States of America

Fibre Chemistry

Pharmacological Reviews

Israel Journal of Chemistry

Kinetics and Catalysis

Organic Preparations and Procedures International

Science Progress

European Journal of Wood and Wood Products

Science
Related Literature
Additive-free regio- and diastereoselective construction of fully-substituted isoxazolidines employing diazo compounds
Ekta Gupta, Mohd Khalid Zaheer, Ruchir Kant
DOI: 10.1039/C8QO01421C
Efficient synthesis of multisubstituted 2-alkenylpyridines via 2,3-rearrangement of O-homoallenylic oximes
Itaru Nakamura, Yoshiharu Oyama, Dong Zhang
DOI: 10.1039/C6QO00703A
Fast construction of dianthraceno[a,e]pentalenes for OPV applications
Haijun Fan
DOI: 10.1039/C6QO00867D
Planar versus triptycenylene end-capped aroyleneimidazoles as electron acceptors in organic photovoltaics
DOI: 10.1039/C7QO00231A
From tetrabenzoheptafulvalene to sp2 carbon nano-rings
Kwan Yin Cheung, Shuaijun Yang, Qian Miao
DOI: 10.1039/C6QO00828C
Visible light enabled γ-trifluoromethylation of Baylis–Hillman acetates: stereoselective synthesis of trisubstituted alkenes
Arvind Kumar Yadav, Anup Kumar Sharma, Krishna Nand Singh
DOI: 10.1039/C9QO00166B
Chiral phosphoric acid-catalyzed asymmetric C(sp3)–H functionalization of biomass-derived 2,5-dimethylfuran via two sequential Cope-type rearrangements
Lubin Xu, Haohua Chen, Jian Liu, Lan Zhou, Qing Liu
DOI: 10.1039/C8QO01375F
Palladium-catalyzed β-selective C(sp2)–H carboxamidation of enamides by isocyanide insertion: synthesis of N-acyl enamine amides
Zhuang Xiong, Dongdong Liang, Shuang Luo
DOI: 10.1039/C7QO00049A
The impact of interplay between electronic and steric effects on the synthesis and the linear and non-linear optical properties of diketopyrrolopyrrole bearing benzofuran moieties
Anna Purc, Beata Koszarna, Irina Iachina, Daniel H. Friese, Mariusz Tasior, Krzysztof Sobczyk, Tomasz Pędziński, Jonathan Brewer, Daniel T. Gryko
DOI: 10.1039/C6QO00869K
You might also like
What precautions should be taken when handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3)?
When handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3), safety go...
What is 4-(3,5-Difluorophenyl)aniline (CAS: 405058-00-6)?
4-(3,5-Difluorophenyl)aniline is an aromatic organic compound with the CAS numbe...
How is 5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid (CAS: 338982-07-3) typically synthesized?
5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid can ...
What is the market or research trend for 4-Benzylaniline hydrochloride (CAS: 6317-57-3)?
The market for 4-Benzylaniline hydrochloride (CAS: 6317-57-3) is steadily growin...
Is [3-(Diethylsulfamoyl)phenyl]boronic acid (CAS: 871329-58-7) safe?
[3-(Diethylsulfamoyl)phenyl]boronic acid is generally considered safe when handl...
What are the main uses of 3-Bromo-2,5-dimethoxyaniline (CAS: 115929-62-9)?
3-Bromo-2,5-dimethoxyaniline is mainly used in the pharmaceutical and chemical i...
What regulatory guidelines apply to N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7)?
N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7) is subject to ...
What industries use Carbamic acid, N-[(5S)-5,6-diamino-6-oxohexyl]-, 1,1-dimethylethyl ester (CAS: 24828-96-4)?
This compound is primarily used in the pharmaceutical industry for the synthesis...
How should 2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) be stored?
2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) sho...
What industries use Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9)?
Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9) is utilized in the pharma...
Source Journal
Green Chemistry

Green Chemistry provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on, but not limited to, the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998). Green chemistry is the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry is at the frontiers of this continuously-evolving interdisciplinary science and publishes research that attempts to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. Submissions on all aspects of research relating to the endeavour are welcome. The journal publishes original and significant cutting-edge research that is likely to be of wide general appeal. To be published, work must present a significant advance in green chemistry. Papers must contain a comparison with existing methods and demonstrate advantages over those methods before publication can be considered. For more information please see this Editorial. Coverage includes the following, but is not limited to: Design (e.g. biomimicry, design for degradation/recycling/reduced toxicity…) Reagents & Feedstocks (e.g. renewables, CO2, solvents, auxiliary agents, waste utilization…) Synthesis (e.g. organic, inorganic, synthetic biology…) Catalysis (e.g. homogeneous, heterogeneous, enzyme, whole cell…) Process (e.g. process design, intensification, separations, recycling, efficiency…) Energy (e.g. renewable energy, fuels, photovoltaics, fuel cells, energy storage, energy carriers…) Applications (e.g. electronics, dyes, consumer products, coatings, pharmaceuticals, preservatives, building materials, chemicals for industry/agriculture/mining…) Impact (e.g. safety, metrics, LCA, sustainability, (eco)toxicology…) Green chemistry is, by definition, a continuously-evolving frontier. Therefore, the inclusion of a particular material or technology does not, of itself, guarantee that a paper is suitable for the journal. To be suitable, the novel advance should have the potential for reduced environmental impact relative to the state of the art. Green Chemistry does not normally deal with research associated with 'end-of-pipe' or remediation issues.




