Bacterial scission of ether bonds

White, Graham F.; Russell, Nicholas J.; Tidswell, Edward C.

doi:10.1128/mr.60.1.216-232.1996

Cited by 122 publications

(55 citation statements)

References 115 publications

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“…The ether functionality, especially methyl ethers, is rather inert under various conditions and therefore protects the otherwise easily oxidable catechol moiety; yet, this inertness leaves the ether functionality difficult to remove, unless harsh conditions are applied (acid or base) [4] . Since the methyl ether group is widely found in nature, [5] a variety of enzymes are able to transform this moiety such as (i) monooxygenases, [6] (ii) peroxygenases, [7] (iii) dehydratases as observed for PEG degradation [8] and (iv) methyltransferases [9] . Mostly, the methyl ether groups are cleaved by P450 enzymes at the expense of NAD(P)H and molecular oxygen by C−H oxidation at the carbon next to the ether oxygen, resulting in a hemiacetal, which then decomposes [6a, 7c, 10] .…”

Section: Methodsmentioning

confidence: 99%

“…[ 6a , 7c , 10 ] However, the oxidative conditions may cause various challenges;[ 7c , 11 ] e.g., when catechol is the target product, the presence of molecular oxygen may initiate undesired follow‐up reactions (such as polymerization, autooxidation, quinone formation). On the other hand, homoacetogenic bacteria are capable of growing on methyl‐aryl ethers, [5] degrading these compounds as a source of energy. These bacteria use methyltransferases to shuttle the methyl group to an acceptor molecule (e.g.…”

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confidence: 99%

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Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives

et al. 2021

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Demethylating methyl phenyl ethers is challenging, especially when the products are catechol derivatives prone to follow-up reactions. For biocatalytic demethylation, monooxygenases have previously been described requiring molecular oxygen which may cause oxidative side reactions. Here we show that such compounds can be demethylated anaerobically by using cobalamin-dependent methyltransferases exploiting thiols like ethyl 3-mercaptopropionate as a methyl trap. Using just two equivalents of this reagent, a broad spectrum of substituted guaiacol derivatives were demethylated, with conversions mostly above 90 %. This strategy was used to prepare the highly valuable antioxidant hydroxytyrosol on a one-gram scale in 97 % isolated yield.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives

et al. 2021

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“…2c and d were proposed as 100% matching the m/z. Although the cleavage of -C-O-C-of polyGGE can occur driven by enzyme or bacteria to produce oligomer fragments [29], it is not likely to take place at moderate condition, as in case of MEM washing. On the contrary, those oligomers were possibly originating from the monomer.…”

Section: Prediction Of Chloride Substances In the Eluent Of Polygge Via Hplc-esi-msmentioning

confidence: 99%

Prediction of the epichlorohydrin derived cytotoxic substances from the eluent of poly(glycerol glycidyl ether) films

Zhou

et al. 2021

MRS Advances

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Glycerol-based epoxy networks have great potential for surface functionalization, providing anti-microbial and protein repellant function. However, the synthesis of glycerol glycidyl ether (GGE) monomer often requires excessive epichlorohydrin (ECH). ECH derived organochloride containing byproducts from monomer production maybe present in the eluent of the polymer networks prepared by cationic ring-opening polymerization. Here, the cytotoxicity analysis revealed cell damages in contact with the polyGGE eluent. The occurrence of organochlorides, which was predicted based on the data from high-performance liquid chromatography/electrospray ionization mass spectrometry, as confirmed by a constant chloride level in GGE and polyGGE, and by a specific peak of C–Cl in infrared spectra of GGE. The resulting polyGGE was densely crosslinked, which possibly contribute to the trapping of organochlorides. These results provide a valuable information for exploring the toxins leaching from polyGGE and propose a feasible strategy for minimizing the cytotoxicity via reducing their crosslink density. Graphic abstract The eluent of poly(glycerol glycidyl ether) (polyGGE) films impaired the viability and metabolic activity of L-929 cells due to the organochloride byproducts or epichlorohydrin precursors originating from the GGE monomer, which was predicted based on the data from high-performance liquid chromatography/electrospray ionization mass spectrometry (HPLC–ESI–MS) and confirmed by chloride content analysis and attenuated total reflection fourier transform infrared (ATR-FT-IR) spectroscopy.

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“…Trifasciatine C (7) could then be formed from trifasciatine A (5) by enzymatic cleavage of its C-ring through breakage of the ether bond (path a in Figure 2) [4b]. In our opinion, however, this hypothesis does not take into consideration that a) etherase enzymes capable of breaking ether bonds are produced by some bacteria [16], while, to our knowledge, their presence in the biochemical machinery of higher plants is still unknown; b) the ether bond scission in compound 5 to give 7 should be stereospecific, i.e. with preservation of the stereochemical integrity of the stereogenic center C(3).…”

Section: Biosynthetic Considerationsmentioning

confidence: 99%

Constituents of the Rhizomes of Sansevieria cylindrica

Aye

Aung²,

Thu³

et al. 2018

Natural Product Communications

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A new sappanin-type 3-benzyl chroman-4-one (homoisoflavanone), (3S)-3-(4′-methoxybenzyl)-3,5-dihydroxy-7-methoxy-6-methyl chroman-4-one (1), together with known congeners (3S)-3-(4′-methoxybenzyl)-3,5-dihydroxy-7-methoxy chroman-4-one (2), (3S)-3-(4′-hydroxybenzyl)-3,5-dihydroxy-7methoxy-6-methyl chroman-4-one (3), (3S)-3-(4′-hydroxybenzyl)-3,5-dihydroxy-7-methoxy chroman-4-one (4), 3-(3',4'-methyledioxybenzyl)-7-hydroxy-8methoxy chroman-4-one (5), and stigmasterol and ergosterol peroxide have been isolated from the rhizomes of Sansevieria cylindrica, collected in Myanmar. Moreover, the first isolation of the (-)-enantiomer of the dihydrochalcone trifasciatine C (7) from nature is described. The structures of the compounds have been established by extensive spectroscopic analysis. Compounds 4 and 7 showed no significant cytotoxicity against HeLa cells. Compounds 1-4 and 7 exhibited weak radical scavenging activity (DPPH). A new biosynthetic pathway has been proposed for the formation of homoisoflavanone 5 and dihydrochalcone 7.

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Bacterial scission of ether bonds

Cited by 122 publications

References 115 publications

Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives

Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives

Prediction of the epichlorohydrin derived cytotoxic substances from the eluent of poly(glycerol glycidyl ether) films

Constituents of the Rhizomes of Sansevieria cylindrica

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