Darstellung und Eigenschaften des <i>trans</i>‐5.6‐Dihydroxy‐cyclohexadiens‐(1.3). Zur Chemie des Benzolglykols, II

Nakajima, Minoru; Tomida, Ichiro; Hashizume, Akito; Takei, Sankichi

doi:10.1002/cber.19560891004

Cited by 21 publications

(5 citation statements)

References 7 publications

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“…cis-and trans-Benzene glycol were prepared by the methods of Nakajima et al (1956Nakajima et al ( , 1959. Materials used for disc electrophoresis were supplied by Kodak Ltd., Kirkby, Liverpool, U.K. NAD+, NADP+, GSH, 1,10-phenanthroline, dithiothreitol, protamine sulphate, bovine serum albumin, L-amino acid oxidase, glutamic dehydrogenase and ovalbumin were frorn Sigma (London) Ltd., Kingston-upon-Thames, Surrey, U.K. p-Chloromercuribenzoic acid, catechol, FMN and FAD were from Koch-Light Laboratories Ltd., Colnbrook, Bucks., U.K. p-Galactosidase and fumarase were from The Boehringer Corp. (London) Ltd., Ealing, London W.5, U.K. All other reagents were supplied by BDH Chemicals Ltd., Poole, Dorset, U.K., except where stated in the text.…”

Section: Methodsmentioning

confidence: 99%

The metabolism of benzene by bacteria. Purification and some properties of the enzyme cis-1,2-dihydroxycyclohexa-3,5-diene (nicotinamide–adenine dinucleotide) oxidoreductase (cis-benzene glycol dehydrogenase)

Axcell

Geary

1973

Biochemical Journal

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1. cis-Benzene glycol dehydrogenase was purified to a homogeneous state from a species of Pseudomonas grown with benzene as the major carbon source. 2. The enzyme was specific for the cis-isomer of its substrate and required NAD(+) as hydrogen acceptor. 3. Partial inactivation of the enzyme, which was observed during purification, could be reversed by the addition of Fe(2+) and GSH. 4. A molecular weight of 440000 was calculated from data obtained by sedimentation-velocity and diffusion analysis in the ultracentrifuge. Sodium dodecyl sulphate polyacrylamide-gel electrophoresis indicated a subunit of molecular weight 110000. 5. p-Chloromercuribenzoic acid and 1,10-phenanthroline were shown to inhibit the enzyme.

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Section: Methodsmentioning

confidence: 99%

The metabolism of benzene by bacteria. Purification and some properties of the enzyme cis-1,2-dihydroxycyclohexa-3,5-diene (nicotinamide–adenine dinucleotide) oxidoreductase (cis-benzene glycol dehydrogenase)

Axcell

Geary

1973

Biochemical Journal

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“…Muconaldehyde is the major product in the oxidation of benzene and benzene oxide/oxepin as well. It is a widely investigated product [32][33][34][35][36][37][38]46] not only because of its multiform toxicity but also as a reactive six-carbon diene dialdehyde.…”

Section: Resultsmentioning

confidence: 99%

“…The aldol reaction was carried out with Bn 2 NH·TFA and pip.AcOH and after PTLC (ethyl acetate-hexane 2:3) the E,E-muconaldehyde 17[32][33][34][35][36][37][38] was isolated as pale yellow crystals; R f 0.53; 53% (58 mg) using Bn 2 NH·TFA and 54% (60 mg) with pip.AcOH, m.p. 120 • C (literature 121 • C [32,34-38], 117 • C [33]), IR 990.2, 1090.0, 1092.7, 1586.2, 1682.4, 2740.4, 2825.1; 1 H NMR…”

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confidence: 99%

A study on the intramolecular catalytic aldol cyclodehydration of 3,4-disubstituted 1,6-dialdehydes

Kurteva

Afonso

2005

Journal of Molecular Catalysis A: Chemical

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“…Similarly, base catalysed cyclisation of I,S-di-carbonyl carbohydrate derivatives has been applied to the synthesis of branched chain cyclitols. Treatment of 1,7-dichloro-hepto-2,6-diulose (73)…”

Section: B Application Of the Diels-alder Reaclionmentioning

confidence: 99%

Synthesis of Functionalised Cyclohexanes from Carbohydrates

Blattner¹

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<p>Beta-D-glucopyranose pentaacetate was photobrominated to give the 5-baromide from which 6-deoxy-Beta-D-xylo-hex-5-enopyranose tetraacetate was obtained by reductive elimination. This reaction sequence represents an efficient new route to the 5-ene. A detailed investigation into the photobromination of Beta-D-glucopyranose pentaacetate with bromine and with NBS led to the isolation of several by-products containing bromine substituents at C-1 and/or C-5; their reactions with zinc-acetic acid were studied, and the conformations. in solution of four alkenes derived from the 5-bromo compound were determined. 2,3,4-Triacylated 2,3,4,5-tetrahydroxycyclohexanones were Obtained by mercury (II) catalysed rearrangement of 5-deoxyhex-5-enopyranose esters. The mechanism of this rearrangement, and some enopyranose esters The mechanism of this rearrangement, reactions of the products were examined. The use of these new carbocyclic compounds in the synthesis of branched-chain cyclitol derivatives was explored. By means of diazomethane or, alternatively, hydrogen cyanide, substituted cyclohexanes with one-carbon branches and tertiary hydroxyl groups at the site of chain-branching were preared. Attempts to eliminate water from these tertiary alcohols to give substituted cyclohexene-carbonitriles or -carbaldehydes were unsuccessful.</p>

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Darstellung und Eigenschaften des trans‐5.6‐Dihydroxy‐cyclohexadiens‐(1.3). Zur Chemie des Benzolglykols, II

Cited by 21 publications

References 7 publications

The metabolism of benzene by bacteria. Purification and some properties of the enzyme cis-1,2-dihydroxycyclohexa-3,5-diene (nicotinamide–adenine dinucleotide) oxidoreductase (cis-benzene glycol dehydrogenase)

The metabolism of benzene by bacteria. Purification and some properties of the enzyme cis-1,2-dihydroxycyclohexa-3,5-diene (nicotinamide–adenine dinucleotide) oxidoreductase (cis-benzene glycol dehydrogenase)

A study on the intramolecular catalytic aldol cyclodehydration of 3,4-disubstituted 1,6-dialdehydes

Synthesis of Functionalised Cyclohexanes from Carbohydrates

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