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  • 1
    Electronic Resource
    Electronic Resource
    Herkunft des Sauerstoffatoms im Furanring von F-Säuren (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 861-863 
    Details
    ISSN: 0170-2041
    Keywords: Furan fatty acids ; Saccharum spec. ; Cell suspension culture ; 18O2-Labelling ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Origin of the Oxygen Atom in the Furan Ring of F AcidsIncubation experiments with 18O2 gas on suspension cultures of Saccharum spec. demonstrate that the oxygen atom in the furan ring of F acids 1 is derived from the air. This result points to the participation of lipoxygenase systems in the biosynthesis of these compounds. Specific incorporation into the furan ring, using an apparatus with 18O2 influx in portions, was confirmed by GC/MS analysis of the tetrahydofuran derivatives 2, obtained by esterification and hydrogenation of the corresponding furan derivatives 1.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1991199101148
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  • 2
    Electronic Resource
    Electronic Resource
    Epoxidierung von Kohlenstoff-Kohlenstoff-Doppelbindungen in Terpenen durch Linolsäurehydroperoxide (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1253-1256 
    Details
    ISSN: 0170-2041
    Keywords: Terpenes ; Epoxides ; Linoleic acid derivatives ; Hydroperoxides ; Labeled compounds, 18O2 ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Epoxidation of Carbon-Carbon Double Bonds in Terpenes by Linoleic Acid HydroperoxidesEpoxidation of C=C double bonds in terpenes is achieved by reaction with linoleic acid hydroperoxides (LOOH) exemplified with caryophyllene (3), methyl farnesoate (5) and squalene (8). Linoleic acid (9S)-hydroperoxide was obtained by reaction of linoleic acid (1) with lipoxygenase present in tomato homogenisate. When 18O2-labeled (9S)-LOOH (2) was used 18O was found in the terpene epoxide. While 3 is converted under physiological conditions regioselectively in high yiled into its 4,5-epoxide 4, the yield of epoxidized products from long-chain molecules, e.g. squalene (8), decreases strongly and no regioselectivity was observed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301204
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  • 3
    Electronic Resource
    Electronic Resource
    Plasmalogenepoxide als biologische Vorstufen von α-Hydroxyaldehyden (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1249-1251 
    Details
    ISSN: 0170-2041
    Keywords: Enol ethers ; Plasmalogens ; Epoxides ; Labeled compounds, 18O2 ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Plasmalogen Epoxides as Biological Precursors of α-HydroxyaldehydesCell damage produces hydroperoxides which in turn are able to oxidize plasmalogens 1 to plasmalogenepoxides 2. These are masked α-hydroxyaldehydes, which can be detected after appropriate derivatization. The detected α-hydroxyaldehydes could also be generated during the preparation procedure of tissue. Experiments carried out with 18O2 demonstrate no incorporation of 18O2 in α-hydroxyaldehydes. Consequently, they are already present in tissue. - Further experiments proved that α-acyloxyplasmalogens 3, recently suggested to be the source of α-hydroxyaldehydes[1,2], do not occur in tissue.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301203
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  • 4
    Electronic Resource
    Electronic Resource
    Bildung von Enolether-Epoxiden durch Einwirkung von (9S,10E,12Z)-Hydroperoxyoctadecadiensäure auf Plasmalogene (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1245-1248 
    Details
    ISSN: 0170-2041
    Keywords: Enol ethers ; Epoxides ; Octadecadienoic acid, (9S,10E,12Z)-hydroperoxy- ; Plasmalogens ; Labelled compounds, 18O2 ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Formation of Enol Ether Epoxides by Reaction of (9S,10E,12Z)-Hydroperoxyoctadecadienoic Acid with Plasmalogens(9S,10E,12Z)-Hydroperoxyoctadecadienoic acid (8a) oxidizes enol ethers (e.g. 2 and neutral plasmalogens 3) under physiological conditions (pH = 6.6, room temperature). The reaction products, unstable enol ether epoxides 9a and 10a, react as recently demonstrated with methanol to α-hydroxyaldehyde dialkyl acetals 11a or with 1,2-ethanedithiol to 2-(α-hydroxyalkyl)dithiolans 13a which can be detected by GC/MS after trimethylsilylation. If [18O2]-(9S,10E,12Z)-hydroperoxy-octadecadienoic acid (8b) is used instead of 8a one atom of 18O is incorporated into the enol ether epoxide and found in the α-hydroxy group of the aldehyde derivatives 11 and 13.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301202
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  • 5
    Electronic Resource
    Electronic Resource
    Enoletherepoxide und ihre Reaktionsprodukte mit Nucleophilen (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 17-21 
    Details
    ISSN: 0170-2041
    Keywords: Enol ethers ; Dioxirane, dimethyl ; Epoxides ; Acetals ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enol Ether Epoxides and Products Resulting from Their Reaction with Nucleophiles1,2-Epoxydecyl pentyl ether (9a) was synthesized by treatment of 1-decenyl pentyl ether (5) with diemthyldioxirane (8). The enol ether epoxide 9a, characterized by its mass, 1H- and 13C-NMR spectra, reacts readily with hydride, O-, S- and N-nucleophiles. Similar reactions are expected to take place in the organism after biological oxidation of plasmalogens to their epoxides. This hypothesis is verified by detection of mixed acetals after tissue workup.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930105
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