Biocatalytic Methyl Ether Cleavage: Characterization of the Corrinoid‐Dependent Methyl Transfer System from Desulfitobacterium hafniense
Abstract: The ether functionality represents a very common motif in organic chemistry and especially the methyl ether is commonly found in natural products. Its formation and cleavage can be achieved via countless chemical procedures. Nevertheless, since in particular the cleavage often involves harsh reaction conditions, milder alternatives are highly demanded. Very recently, we have reported on a biocatalytic shuttle catalysis concept for reversible cleavage and formation of phenolic O‐methyl ethers employing a corrinoid‐dependent methyl transferase system from the anaerobic organism Desulfitobacterium hafniense. Here we report the technical study of this system, focusing on the demethylation of guaiacol as model reaction. The optimal buffer‐, pH‐, temperature‐ and cofactor‐preferences were determined as well as the influence of organic co‐solvents. Beside methyl cobalamin also hydroxocobalamin turned out to be a suitable cofactor species, although the latter required activation. Various O‐methyl phenyl ethers were successfully demethylated with conversions up to 82% at 10 mM substrate concentration.
- Location
-
Deutsche Nationalbibliothek Frankfurt am Main
- Extent
-
Online-Ressource
- Language
-
Englisch
- Bibliographic citation
-
Biocatalytic Methyl Ether Cleavage: Characterization of the Corrinoid‐Dependent Methyl Transfer System from Desulfitobacterium hafniense ; volume:361 ; number:11 ; year:2019 ; pages:2688-2695 ; extent:8
Advanced synthesis & catalysis ; 361, Heft 11 (2019), 2688-2695 (gesamt 8)
- Creator
-
Richter, Nina
Farnberger, Judith E.
Pompei, Simona
Grimm, Christopher
Skibar, Wolfgang
Zepeck, Ferdinand
Kroutil, Wolfgang
- DOI
-
10.1002/adsc.201801590
- URN
-
urn:nbn:de:101:1-2022072707432173398931
- Rights
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
-
15.08.2025, 7:26 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Richter, Nina
- Farnberger, Judith E.
- Pompei, Simona
- Grimm, Christopher
- Skibar, Wolfgang
- Zepeck, Ferdinand
- Kroutil, Wolfgang
Other Objects (12)
Synthesis of Estrone Methyl Ether
Synthesis of Estrone Methyl Ether
Grignard Reactions in Cyclopentyl Methyl Ether
Methoxypropanol (propylene glycol methyl ether) : (October 1995)
A Catalytic, Oxidative Synthesis of Olivetol, Methyl Olivetolate and Orthogonally Protected Methyl Ether Derivatives
Methyl tert-butyl ether (MTBE) : health risk characterisation
Rhodium-Catalyzed Asymmetric C–H Functionalization of Methyl Ethers
Methyl tertiary-butyl ether : [IPCS, International Programme on Chemical Safety]
Die endoskopisch-retrograde Cholecystolitholyse mit Methyl-Tert-Butyl-Ether (MTBE)
Glycerol Acetalization in Cyclopentyl Methyl Ether with Mild Acid Catalysts
Methylen
"Methyl"
Synthesis of Estrone Methyl Ether
Synthesis of Estrone Methyl Ether
Grignard Reactions in Cyclopentyl Methyl Ether
Methoxypropanol (propylene glycol methyl ether) : (October 1995)
A Catalytic, Oxidative Synthesis of Olivetol, Methyl Olivetolate and Orthogonally Protected Methyl Ether Derivatives
Methyl tert-butyl ether (MTBE) : health risk characterisation
Rhodium-Catalyzed Asymmetric C–H Functionalization of Methyl Ethers
Methyl tertiary-butyl ether : [IPCS, International Programme on Chemical Safety]
Die endoskopisch-retrograde Cholecystolitholyse mit Methyl-Tert-Butyl-Ether (MTBE)
Glycerol Acetalization in Cyclopentyl Methyl Ether with Mild Acid Catalysts
Methylen
"Methyl"
Synthesis of Estrone Methyl Ether
Synthesis of Estrone Methyl Ether
Grignard Reactions in Cyclopentyl Methyl Ether
Methoxypropanol (propylene glycol methyl ether) : (October 1995)
A Catalytic, Oxidative Synthesis of Olivetol, Methyl Olivetolate and Orthogonally Protected Methyl Ether Derivatives
Methyl tert-butyl ether (MTBE) : health risk characterisation
Rhodium-Catalyzed Asymmetric C–H Functionalization of Methyl Ethers
Methyl tertiary-butyl ether : [IPCS, International Programme on Chemical Safety]
Die endoskopisch-retrograde Cholecystolitholyse mit Methyl-Tert-Butyl-Ether (MTBE)
Glycerol Acetalization in Cyclopentyl Methyl Ether with Mild Acid Catalysts
Methylen