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  • 1
    ISSN: 0570-0833
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1573-4986
    Keywords: sialidase ; neuraminidase ; 5-bromo-indol-3-yl α-ketoside of 5-N-acetyl-d-neuraminic acid ; electrophoresis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The purification and characterisation of viral, bacterial and mammalian sialidases (EC 3.2.1.18, neuraminidases, neuraminosylglycohydrolases) prompted a search for a colorimetric technique to localize the enzymes on electropherograms. The 5-bromo substituted indol-3-yl α-ketoside of 5-N-acetyl-d-neuraminic acid (BIN), the synthesis of which is described here, seemed to be the appropriate substrate, because of its relative ease of enzymatic hydrolysis to 5-N-acetyl-d-neuraminic acid and 5-bromoindoxyl. The latter is readily transformed to the insoluble, intensely coloured 5,5′-dibromo-indigo. This precipitates and can be seen readily at the sites of enzymatic activity. The new substrate is of definitive advantage as it provides a simple and direct method for the demonstration of sialidases without the need of a coupling reaction.
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 762 (1972), S. 160-166 
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Nucleoside Analogues of 5-HydroxymethyluracilThe hydroxymethyl group of 5-hydroxymethyluracil (1a) reacts with 2,3-dihydrofuran and -pyran in the presence of acid catalysts to form 2a and 2b, respectively. N1,N3-Dimethyl-5-hydroxymethyluracil (1b) reacts analogously. By condensation of persilylated 1a (3) with 2-chlorotetrahydrofuran or 2-chlorotetrahydropyran the corresponding N3-substituted derivatives 5 and 4 are obtained. The nucleoside analogues are converted into the compounds 2e-2h by reaction of the hydroxymethyl group with 2,3-dihydrofuran and -pyran, respectively. In these substances two oxygen-containing rings are connected with uracil. These biologically interesting compounds can be regarded as models of the naturally occuring 5-O-glycoside derivatives of 5-hydroxymethylcytosine.
    Notes: Die Hydroxymethylgruppe des 5-Hydroxymethyl-uracils (1a) liefert bei der säurekatalysierten Reaktion mit 2.3-Dihydro-furan bzw. -pyran die Verbindungen 2a bzw. 2b. Analog reagiert N1.N3-Dimethyl-5-hydroxymethyl-uracil (1b) zu 2c bzw. 2d. Kondensation von persilyliertem 1a (3) mit 2-Chlor-tetrahydrofuran bzw. -tetrahydropyran führt zu den entsprechenden N3-substituierten Verbindungen 5 bzw. 4. Diese Nucleosid-Analoga setzen sich mit 2.3-Dihydro-furan bzw. -pyran an der 5-ständigen Hydroxymethylgruppe zu den Verbindungen 2e-2h um, in denen zwei sauerstoffhaltige Ringe mit Uracil verknüpft sind. Diese biologisch interessanten Verbindungen sind Modelle für das natürlich vorkommende 5-O-glykosidierte 5-Hydroxymethyl-cytosin.
    Additional Material: 1 Tab.
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1977 (1977), S. 1969-1975 
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Mono-, Di-, and Triallyl Derivatives of 5-(Hydroxymethyl)uracilThe syntheses of variously substituted allyl compounds of 5-(hydroxymethyl)uracil (1) are described. After treatment with hexamethyldisilazane and allyl bromide 1 is converted into 1-allyl-5-(hydroxymethyl)uracil (5). A facile general synthesis for a number of 5-(allyloxymethyl)uracil derivatives is reported.
    Notes: Die Synthesen verschieden substituierter Allylderivate des 5-(Hydroxymethyl)uracils (1) werden beschrieben. 1 ergibt nach der Umsetzung mit Hexamethyldisilazan und Allylbromid 1-Allyl-5-(hydroxymethyl)uracil (5). Eine einfache Darstellung substituierter 5-(Allyloxy-methyl)uracile wird diskutiert.
    Additional Material: 1 Tab.
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  • 5
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of 5-(β-D-Glucopyranosyloxymethyl)uracil and 1,3-Dimethyl-5-(β-D-glucopyranosyloxymethyl)uracil5-(Hydroxymethyl)uracil (1) and 5-hydroxymethyl-1,3-dimethyluracil (4) react with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose in the presence of boron trifluoride-etherate to yield 5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)uracil (6) and 1,3-dimethyl-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)uracil (7). Removal of the protecting groups produces the acid-sensitive glucosides 6a and 7a, respectively. The configuration at C-1 of the glycosidic bond was confirmed by 1H-NMR spectroscopy.
    Notes: 5-(Hydroxymethyl)uracil (1) und 5-Hydroxymethyl-1,3-dimethyluracil (4) reagieren in Gegenwart von Bortrifluorid-ätherat mit 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranose zu 5-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxymethyl)uracil (6) bzw. 1,3-Dimethyl-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)uracil (7). Abspaltung der Schutzgruppen führt zu den im Titel genannten säurelabilen Glucosiden 6a und 7a, deren Konfiguration der glykosidischen Bindung an C-1 1H-NMR-spektroskopisch ermittelt wurde.
    Additional Material: 1 Tab.
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  • 6
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses of 5-(α-D-Glucopyranosyloxymethyl)-3-(β-D-ribofuranosyl)uracil and 3-(2-Deoxy-β-D-ribofuranosyl)-5-(α-D-glucopyranosyloxymethyl)uracil as Analogues of a DNA Structural Unit**5-(α-D-Glucopyranosyloxymethyl)uridine (4a), 5-(α-D-glucopyranosyloxymethyl)-2′-deoxyuridine (6a) and its β-anomer 5a have been synthesized by reaction of the aglycons 1 and 2, respectively, with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (3) in the presence of boron trifluoride-etherate and removal of the protecting groups. The configuration at C-1 of the carbohydrate moiety of this new class of pyrimidine nucleosides has been established by 1H-NMR spectroscopy.
    Notes: 5-(α-D-Glucopyranosyloxymethyl)uridin (4a), 5-(α-D-Glucopyranosyloxymethyl)-2′-desoxyuridin (6a) sowie sein β-Anomeres 5a erhält man durch Reaktion der Aglykone 1 bzw. 2 mit 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranose (3) in Gegenwart von Bortrifluorid-ätherat und Abspaltung der Schutzgruppen. Die Konfiguration an C-1 der Kohlenhydratkomponente dieser neuen Klasse von Pyrimidin-nucleosiden wurde durch 1H-NMR-Spektroskopie bestimmt.
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  • 7
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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