A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids

Zhao, Mangzhu; Li, Jing; Song, Zhiguo J.; Desmond, Richard; Tschaen, David M.; Grabowski, Edward J. J.; Reider, Paul J.

doi:10.1016/s0040-4039(98)00987-3

Cited by 210 publications

(108 citation statements)

References 15 publications

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“…The extracts were pooled and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the cis-3-decenol was converted to cis-3-decenoic acid by chromic trioxide-catalyzed periodate oxidation (23). After quenching the reaction by addition of ethanol the acid was extracted first into ether/pentane (1/1) and then from that solution into 1 M potassium bicarbonate to remove any remaining cis-3-decenol.…”

Section: Methodsmentioning

confidence: 99%

Escherichia coli Unsaturated Fatty Acid Synthesis

Feng

Cronan

2009

Journal of Biological Chemistry

163

108

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Although the unsaturated fatty acid (UFA) synthetic pathway of Escherichia coli is the prototype of such pathways, several unresolved issues have accumulated over the years. The key players are the fabA and fabB genes. Earlier studies of fabA transcription showed that the gene was transcribed from two promoters, with one being positively regulated by the FadR protein. The other weaker promoter (which could not be mapped with the technology then available) was considered constitutive because its function was independent of FadR. However, the FabR negative regulator was recently shown to represses fabA transcription. We report that the weak promoter overlaps the FadR-dependent promoter and is regulated by FabR. This promoter is strictly conserved in all E. coli and Salmonella enterica genomes sequenced to date and is thought to provide insurance against inappropriate regulation of fabA transcription by exogenous saturated fatty acids. Also, the fabAup promoter, a mutant promoter previously isolated by selection for increased FabA activity, was shown to be a promoter created de novo by a four-base deletion within the gene located immediately upstream of fabA. Demonstration of the key UFA synthetic reaction catalyzed by FabB has been elusive, although it was known to catalyze an elongation reaction. Strains lacking FabB are UFA auxotrophs indicating that the enzyme catalyzes an essential step in UFA synthesis. Using thioesterases specific for hydrolysis of short chain acyl-ACPs, the intermediates of the UFA synthetic pathway have been followed in vivo for the first time. These experiments showed that a fabB mutant strain accumulated less cis-5-dodecenoic acid than the parental wild-type strain. These data indicate that the key reaction in UFA synthesis catalyzed by FabB is elongation of the cis-3-decenoyl-ACP produced by FabA.The fabA gene of Escherichia coli encodes 3-hydroxydecanoyl-acyl carrier protein (ACP) 2 dehydratase/isomerase, a bifunctional enzyme that introduces the unsaturated fatty acid (UFA) double bond at the C10 level (1-3) (see Fig. 1). As expected fabA mutants require supplementation with UFA for growth (4). Although UFA synthesis can be considered a housekeeping function, fabA transcription is subject to an unexpectedly complex regulation. Work from this laboratory and others showed that fabA transcription is positively regulated by FadR, a protein that also functions as the repressor of the ␤-oxidation regulon (5-7). In that work the FadR-dependent promoter was identified as well as a second weaker promoter that was unaffected by FadR and thus was considered constitutively active (5, 6). The FadR-independent promoter is thought to ensure continued expression of fabA under conditions where FadR activation is compromised. E. coli fabA mutants lyse in the absence of UFA (3). Because FadR responds to CoA thioesters of both unsaturated and saturated fatty acids, E. coli could shut down UFA synthesis in response to saturated fatty acid (SFA) availability, a potential disaster. We have proposed that E. ...

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Section: Methodsmentioning

confidence: 99%

Escherichia coli Unsaturated Fatty Acid Synthesis

Feng

Cronan

2009

Journal of Biological Chemistry

163

108

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“…Control experiments were designed to assess the catalytic activity of Fe(III) and PA. As indicated in Table 1, H 5 IO 6 itself possesses some oxidative function that can be somewhat enhanced by presence of Fe(III). Addition of PA then greatly improves the oxidation power in terms of reaction time and yield.…”

Section: Resultsmentioning

confidence: 95%

“…The reactivity decreases in the order of In conclusion, H 5 IO 6 /Fe(III)/PA in pyridine is an efficient and selective reagent that can convert the alcohols to their aldehydes and ketones. The process utilizing H 5 IO 6 /Fe(III) should be environmentally benign.…”

Section: Resultsmentioning

confidence: 99%

Oxidation of Alcohols with Periodic Acid Catalyzed by Fe(III)/2‐Picolinic Acid.

2003

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“…6 However, most of these systems required use of large excesses of oxidants, harsh reaction conditions, and expensive promoters. In particular, molecular oxygen has been utilized for the oxidation of benzylic alcohols in combination with complexes of transition metals such as palladium, 7 ruthenium, 8 iridium, 9 cobalt, 10 or copper. 11 However, most of the aforementioned reagent systems are generally exotic, toxic, and expensive which limit their practical applications.…”

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confidence: 99%

Oxidation of Benzylic Alcohols with Urea Hydrogen Peroxide/Calcium Chloride in PEGDME₂₅₀

Ha¹,

Jung²,

Kim³

et al. 2014

Bulletin of the Korean Chemical Society

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A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids

Cited by 210 publications

References 15 publications

Escherichia coli Unsaturated Fatty Acid Synthesis

Escherichia coli Unsaturated Fatty Acid Synthesis

Oxidation of Alcohols with Periodic Acid Catalyzed by Fe(III)/2‐Picolinic Acid.

Oxidation of Benzylic Alcohols with Urea Hydrogen Peroxide/Calcium Chloride in PEGDME₂₅₀

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A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids

Cited by 210 publications

References 15 publications

Escherichia coli Unsaturated Fatty Acid Synthesis

Escherichia coli Unsaturated Fatty Acid Synthesis

Oxidation of Alcohols with Periodic Acid Catalyzed by Fe(III)/2‐Picolinic Acid.

Oxidation of Benzylic Alcohols with Urea Hydrogen Peroxide/Calcium Chloride in PEGDME250

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Oxidation of Benzylic Alcohols with Urea Hydrogen Peroxide/Calcium Chloride in PEGDME₂₅₀