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  • 1
    Electronic Resource
    Electronic Resource
    Electrochemical Reduction in an Aprotic Medium of New Functionalized Amphiphilic Molecules Derived from Sugars: Stereoselective Pinacolization and an Example of a Glycosidic Carbon-Oxygen Bond Cleavage (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 813-821 
    Details
    ISSN: 1434-193X
    Keywords: Amphiphiles ; Ketone ; Glycosides ; Electron transfer ; Chiral resolution ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---Electroreducible amphiphilic aromatic ketones derived from D-glucose and D-glucofuranurono-6,3-lactone (D-glucurone) have been synthesized by Schmidt condensation and reaction of the unprotected lactone with the appropriate substrates, respectively. The macroscale electrolyses of the glucose derivatives, performed in an aprotic solvent (DMF), yield the pinacols possessing two glycosidic side chains. Under the same conditions of electrolysis with the D-glucurone derivative, the glyosidic carbon-oxygen bond is cleaved. The use of a redox mediator (couple anthracene-•/anthracene) has demonstrated that a glucosidic bond can be reduced by a homogeneous electron transfer. In the presence of a proton donor the expected D-glucuronic pinacol is obtained. The radical-radical coupling involves the formation of two chiral centers. The diastereo- and the enantioselectivity of the reaction have been studied by 1H- and 2H-NMR spectroscopy, respectively.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    Redox labeling of two antiepileptic drugs with metallocenes and their simultaneous detection by a Nafion-modified electrode (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 12 (1998), S. 59-65 
    Details
    ISSN: 0268-2605
    Keywords: cobaltocenium ; ferrocene ; Nafion ; phenytoin ; phenobarbital ; square-wave voltammetry ; Chemistry ; Industrial Chemistry and Chemical Engineering
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two different cationic redox labels, i.e. a ferroceneammonium ion and a cobaltocenium ion, were covalently attached to two antiepileptics, phenytoin and phenobarbital, respectively. The two labeled drugs possess distinct standard redox potentials of 0.39 V for the phenytoin derivative and -0.92 V for phenobarbital derivative (vs Ag/AgCl, Cl- 0.05 M) at a carbon paste electrode. After preconcentration in a polyanionic Nafion-loaded carbon paste electrode the positively charged labeled phenytoin and phenobarbital derivatives could be simultaneously detected in concentration ranges which were relevant to the therapeutic ranges of the antiepileptics, with a view to a future dual-analyte immuno- assay. Square-wave voltammetry permitted detection limits of 5×10-8 M (for the phenytoin derivative) and 2.5×10-8 M (for the phenobarbital derivative) for non-simultaneous detection. © 1998 John Wiley & Sons, Ltd.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
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    Paper (German National Licenses)
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