Stereochemistry of the Conversion of 2‐Phenoxyethanol into Phenol and Acetaldehyde by <i>Acetobacterium</i> sp.

Speranza, Giovanna; Mueller, Britta; Orlandi, Maximilian; Morelli, Carlo F.; Manitto, Paolo; Schink, Bernhard

doi:10.1002/hlca.200390212

Cited by 9 publications

(7 citation statements)

References 21 publications

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“…3 This phenomenon was related to the loss of enzymatic activity when biomass is not exposed to this solvent. The same study proposed that the ether cleavage of M2P included the transhydroxylation reaction based on that reported by Speranza et al 22 It has also been reported that co-factor B 12, herein metabolized from CoCl 2 , could act as a catalyst of the transhydroxylation reaction of glycol ethers. 23 In this regard, EPS may have significant cobalt sorption capacity, 24 and it could play a key role in the bioavailability of this metal to bacteria.…”

Section: Flocculation Testmentioning

confidence: 79%

Enhancement of biomass retention in an EGSB reactor used to treat 1‐methoxy‐2‐propanol

Lafita

San‐Valero

Marzal

et al. 2017

J of Chemical Tech & Biotech

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BACKGROUND An expanded granular sludge bed (EGSB) reactor is commonly used in anaerobic treatment of industrial wastewater. To develop applications to remove solvents, the granular sludge retention within the reactor must be improved. RESULTS This work evaluated the addition of chitosan as a strategy to enhance granulation in an EGSB reactor used to treat a wastewater containing 1‐methoxy‐2‐propanol and ethanol. Two reactors, one with chitosan supplementation and the other without chitosan (control), were operated in parallel. Greater particle size was obtained in the reactor with chitosan. The retention of solids within the reactor was clearly improved. Moreover, the settling properties were clearly enhanced in the first stages (days 0–44) in terms of settling velocity and sludge volume index. The time required to obtain 80% removal of 1‐methoxy‐2‐propanol was shortened from 38 days to 22 days when chitosan was supplemented. CONCLUSIONS The addition of chitosan is a promising alternative to enhance granulation in EGSB reactors that are used to treat glycol ethers. A single addition rapidly improves the settling properties of the granular sludge; this method could be used as an operational strategy when partial degranulation occurs. This work provides useful guidelines on the enhancement of biomass retention while operating an EGSB. © 2017 Society of Chemical Industry

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Section: Flocculation Testmentioning

confidence: 79%

Enhancement of biomass retention in an EGSB reactor used to treat 1‐methoxy‐2‐propanol

Lafita

San‐Valero

Marzal

et al. 2017

J of Chemical Tech & Biotech

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show abstract

“…17 However, the desired product could not be obtained using any of these routes. Ultimately, we were able to obtain the desired material in 88% yield through the mildly acidic deprotection of dimethyl acetal 15 with Amberlyst-15 resin, 39,40 although the material had to be stored at −20 °C at all times to prevent decomposition.…”

Section: Resultsmentioning

confidence: 99%

A concise enantioselective synthesis and cytotoxic evaluation of the anticancer rotenoid deguelin enabled by a tandem Knoevenagel/conjugate addition/decarboxylation sequence

Farmer

Scheidt

2013

Chem. Sci.

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(−)-Deguelin is a rotenoid natural product that possesses significant potential as a chemopreventive and chemotherapeutic agent. While several racemic syntheses of deguelin have been reported, a formal evaluation of the anticancer activity of both the natural and unnatural enantiomers remains lacking. We describe herein the successful application of a flexible and selective thiourea-catalyzed cyclization strategy toward the enantioselective total synthesis of deguelin, which allows access to either stereoisomer for biological studies. The synthesis was completed in six steps (longest linear) with no protecting groups. The evaluation of both enantiomers of the natural product demonstrated potent inhibition of several cancer cell lines by these compounds, but interestingly showed that the unnatural (+)-deguelin preferentially inhibited the growth of MCF-7 breast cancer and HepG2 liver carcinoma cells when compared to the natural product.

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“…However in two cases of eliminase-catalyzed radical reactions a complete exchange of the mobile H-atom has been observed [28,29]. The biodegradation of the ethanolamines described here appears to be similar to the conversion of 2-phenoxyethanol into acetate mediated by another strain of the anaerobic homoacetogenic bacterium Acetobacterium [30,31]. While adenosylcobalamin (coen- Fig.…”

Section: Resultsmentioning

confidence: 61%

Mechanism of anaerobic degradation of triethanolamine by a homoacetogenic bacterium

Speranza

Morelli

Cairoli

et al. 2006

Biochemical and Biophysical Research Communications

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Triethanolamine (TEA) is converted into acetate and ammonia by a strictly anaerobic, gram-positive Acetobacterium strain LuTria3. Fermentation experiments with resting cell suspensions and specifically deuterated substrates indicate that in the acetate molecule the carboxylate and the methyl groups correspond to the alcoholic function and to its adjacent methylene group, respectively, of the 2-hydroxyethyl unit of TEA. A 1,2 shift of a hydrogen (deuterium) atom from -CH2-O- to =N-CH2- without exchange with the medium was observed. This fact gives evidence that a radical mechanism occurs involving the enzyme and/or coenzyme molecule as a hydrogen carrier. Such a biodegradation appears analogous to the conversion of 2-phenoxyethanol into acetate mediated by another strain of the anaerobic homoacetogenic bacterium Acetobacterium.

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Stereochemistry of the Conversion of 2‐Phenoxyethanol into Phenol and Acetaldehyde by Acetobacterium sp.

Cited by 9 publications

References 21 publications

Enhancement of biomass retention in an EGSB reactor used to treat 1‐methoxy‐2‐propanol

Enhancement of biomass retention in an EGSB reactor used to treat 1‐methoxy‐2‐propanol

A concise enantioselective synthesis and cytotoxic evaluation of the anticancer rotenoid deguelin enabled by a tandem Knoevenagel/conjugate addition/decarboxylation sequence

Mechanism of anaerobic degradation of triethanolamine by a homoacetogenic bacterium

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