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  • 1
    Digitale Medien
    Digitale Medien
    Ein einfacher Weg zu D-Apio-β-D-furanosyl- und 2′-Desoxyapio-β-D-furanosylnucleosiden (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 551-558 
    Details
    ISSN: 0947-3440
    Schlagwort(e): Apionucleosides ; Nucleosides ; Antiviral agents ; Tris(trimethylsilyl)silane ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: A Convenient Route to D-Apio-β-D-furanosyl- and 2′-Deoxyapio-β-D-furanosyl Nucleosides2,3-O-Isopropylidene-D-apio-β-D-furanose (1), available in 40% overall yield by modified literature procedures, is acylated regioselectively to the new 3′-O-benzoyl-derivative 2. This is converted to the anomeric triacetates 4 (β-4; α-4 = 1.8:1) by cleavage of the isopropylidene protecting group from 2 followed by peracetylation. Reaction of compounds 4 with silylated nucleobases and subsequent deprotection gives the D-apio-β-D-furanosyl nucleosides 8-10 in good yields. Regioselective hydrazinolysis of the protected nucleosides 5 and 6 affords the 2′-hydroxy-derivatives 11 and 12, respectively, which are converted to the 2′-deoxyapio-β-D-furanosyl nucleosides 17 and 18, respectively, via deoxygenation of the corresponding thionocarbonates 13 and 14 with tris(trimethylsilyl)silane and subsequent deprotection. The 2′-deoxyapio-β-D-furanosyl cytosine 20 is prepared from the 2′-deoxyapio-β-D-furanosyl uracil derivative 16.
    Zusätzliches Material: 3 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/jlac.199519950375
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  • 2
    Digitale Medien
    Digitale Medien
    Ein einfacher Weg zu 3′-Desoxy-α-L- und 3′-Desoxy-β-D-apionucleosiden (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 559-565 
    Details
    ISSN: 0947-3440
    Schlagwort(e): Apionucleosides ; Nucleosides ; Antiviral agents ; Branched nucleosides ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: A Convenient Route to 3′-Deoxy-α-L- and 3′-Deoxy-β-D-apionucleosidesThe cyclic thionocarbonate 3, easily available in three steps from 3′-O-benzoyl-2,3-O-isopropylidene-D-apio-β-D-furanose (1), is deoxygenated with n-Bu3SnH to yield the 3′-deoxy epimers 4 [methyl 3-C-(benzoyloxymethyl)-3-deoxy-α-L-threo-tetrofuranoside] and 6 [methyl 3-C-(benzoyloxymethyl)-3-deoxy-β-D-erythro-tetrofuranoside]. These are separated by chromatography and further converted to the 3′-deoxy-α-L-apionucleosides 11-13, and the 3′-deoxy-β-D-apionucleosides 17-19, respectively.
    Zusätzliches Material: 2 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/jlac.199519950376
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  • 3
    Digitale Medien
    Digitale Medien
    Structural Variations of N-Acetylneuraminic Acid, 10. Synthesis of 2,7-, 2,8-, and 2,9-Dideoxy- and 2,4,7-Trideoxy-2,3-didehydro-N-acetylneuraminic Acids and Their Behavior Towards Sialidase from Vibrio cholerae (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 159-165 
    Details
    ISSN: 0170-2041
    Schlagwort(e): N-Acetylneuraminic acid ; Sialidase ; Vibrio cholerae ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Beschreibung / Inhaltsverzeichnis: Strukturelle Abwandlungen an N-Acetylneuraminsäure, 101). - Synthese von 2,7-, 2,8- und 2,9-Didesoxy- und 2,4,7-Tridesoxy-2,3-didehydro-N-acetylneuraminsäure und ihr Verhalten gegenüber Sialidase aus Vibrio choleraeDie peracetylierten Methylester-Derivate von 7-Desoxy-Neu5Ac (2c), 8-Desoxy-Neu5Ac (3a), 9-Desoxy-Neu5Ac (4a) und 4,7-Didesoxy-Neu5Ac (5a) wurden mit Trifluormethansulfonsäuretrimethylsilylester in die entsprechenden 2-Desoxy-2,3-didehydro-Derivate 2b-5b umgewandelt, wobei auch in wechselnder Menge die 4,5-Oxazolino-Abkömmlinge 6b-8b gebildet wurden. Hydrolyse von 2b-5b führte zu den freien Säuren 7-Desoxy-Neu5Ac2en (2c), 8-Desoxy-Neu5Ac2en (3c), 9-Desoxy-Neu5Ac2en (4c) und 4,7-Didesoxy-Neu5Ac2en (5c). Diese hemmen die Hydrolyse von 4-Methylumbelliferyl-α-Neu5Ac durch Sialidase aus Vibrio cholerae in einem signifikant unterschiedlichen Ausmaß. Der Vergleich ihrer ermittelten α-Seitenprofile mit demjenigen von Neu5Ac2en ermöglicht ein Verständnis für den sehr unterschiedlichen Einfluß auf die Enzymreaktion.
    Notizen: The peracetylated methyl ester derivatives of 7-deoxy-Neu5Ac (2a), 8-deoxy-Neu5Ac (3a, 9-deoxy-Neu5Ac (4a), and 4,7-dideoxy-Neu5Ac (5a) were transformed by trimethylsilyl trifluoromethanesulfonate into the corresponding 2-deoxy-2,3-didehydro derivatives 2b-5b. As additional products, the 4,5-oxazolino derivatives 6b-8b were formed. Hydrolysis of 2b-5b yielded the free acids 7-deoxy-Neu5Ac2en (2c), 8-deoxy-Neu5Ac2en (3c), 9-deoxy-Neu5Ac2en (4c), and 4,7-dideoxy-Neu5Ac2en (5c). They showed significantly different inhibitory influences on the hydrolysis of 4-methylumbelliferyl-α-Neu5Ac by sialidase from Vibrio cholerae. The comparison of their evaluated α-side profiles with that of Neu5Ac2en (1c) enables a suitable explanation of their different inhibitory potencies.
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/jlac.198919890131
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  • 4
    Digitale Medien
    Digitale Medien
    Structural Variations on N-acetylneuraminic acid, 20. Synthesis of some 2,3-didehydro-2-deoxysialic Acids structurally varied at C-4 and their behavior towards Sialidase from Vibrio cholerae (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 129-134 
    Details
    ISSN: 0170-2041
    Schlagwort(e): N-Acetylneuraminic acid ; Sialidase ; Vibrio cholerae ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The peracetylated methyl ester 1 of N-acetylneuraminic acid was transformed into the oxazoline derivative 2, which was hydrogenated with Pd/C/H2 to give the 4-deoxy-Neu5Ac2en derivative 3. Acid cleavage of the oxazoline 2 by trifluoroacetic acid (THF) gave the 4-epi-Neu5Ac2en derivative 4a, which was saponified to the known 4-epi-Neu5Ac2en 4b. Treatment of 4a with triphenylphosphane/diethylazodicarboxylate (DEAD)/HN3 in toluene gave the 4-azido-4-deoxy-Neu5Ac2en derivative 5a as well as the 4-epi-azido-4-deoxy-Neu5Ac2en derivative 6a. Both epimers could be saponified yielding the free dehydrosialic acid derivatives 5b and 6b. Furthermore, 4-formamido-4-deoxy-Neu5Ac2en 7b was prepared via the derivative 7a, which was formed from 5a by reaction with triphenylphosphane/formyl acetate. In addition, the free dehydrosialic acid derivatives 5b and 6b were transformed into the stable P—N ylides 8 and 10, but only 8 could be hydrolyzed to the triethylammonium salt of 4-amino-4-deoxy-Neu5Ac2en 9a, which was converted into the zwitter ionic compound 9b. Finally 4-acetamido-4-deoxy-Neu5Ac2en 11e was prepared from 4-acetamido-4-deoxy-N-acetylneuraminic acid 10 via the derivatives 11a and 11b by well-known methods. The compounds 4b, 5b, 6b, 7b, 9b, and 11c were investigated as inhibitors of Vibrio cholerae sialidase, and their Ki values were determined.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/jlac.199119910124
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