Anaerobic O-demethylations of methoxynaphthols, methoxyfuran, and fluoroanisols by Sporomusa ovata.
In vitro experiments with 3,4-dimethoxybenzoate-induced Sporomusa enzymes a broad O-methyl ether cleavage capacity. The O-demethylase activity hydrolized the methyl-oxygen linkages of methoxynaphtholes of the heterocycles 2-methoxyfuran or 2-methoxythiophene as well as of several dimethoxy and monomethoxy aryls under anaerobic conditions. Also, fluoro and chloro substituents of anisoles enhanced the O-demethylation rate, indicating that an electron delocalized aromatic structure supported the methyl ether activation mechanism. Monomethoxy aromatics with additional chargeable groups, however, were less effectively transformed by the O-demethylase activity. No transformations into hydroxylated products occurred with 4-(trifluoromethoxy)benzyl alcohol, 4-(trifluoromethoxy)fluorobenzene, 2,5-dimethoxytetrahydrofuran, or alkyl-O-methyl ethers. The inert ethers did not affect the 3,4-dimethoxybenzoate metabolism. Ether activation or the following methyl transfer to the methyl acceptor tetrahydrofolate involved a prominent 31 kDa peptide from the cytoplasmic cell fraction, because this particular peptide was lacking in cells grown with methanol, betaine or fructose.
Stupperich
E
E
University of Ulm, Germany. erhard.stupperich@biologie.uni-ulm.de
Konle
R
R
Eckerskorn
C
C
D000595:Amino Acid Sequence; D000693:Anaerobiosis; D000840:Anisoles / Q000378:metabolism; D001426:Bacterial Proteins / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D004987:Ethers; D005663:Furans / Q000378:metabolism; D006089:Gram-Negative Anaerobic Bacteria / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D006571:Heterocyclic Compounds / Q000378:metabolism*; D008969:Molecular Sequence Data; D009284:Naphthols / Q000378:metabolism; D010089:Oxidoreductases, N-Demethylating / Q000378:metabolism*; D010446:Peptide Fragments / Q000737:chemistry / Q000302:isolation & purification; D013379:Substrate Specificity; D015262:Xenobiotics / Q000378:metabolism*
D000840:Anisoles; D001426:Bacterial Proteins; D004987:Ethers; D005663:Furans; D006571:Heterocyclic Compounds; D009284:Naphthols; D010446:Peptide Fragments; D015262:Xenobiotics; D010089:Oxidoreductases, N-Demethylating