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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 1803-1806 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions with Indole Derivatives, XXVII. Configuration Assignment of Angular Substituted IndoloquinolizinesThe application of spectroscopic data of angular substituted indoloquinolizines for configuration assignment is discussed.
    Notes: Es werden die spektroskopischen Daten angulär substituierter Indolochinolizin-Derivate auf Anwendbarkeit bei der Konfigurationszuweisung überprüft.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 248-259 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions with Indole Derivatives, XXV, The Stereoselective Total Synthesis of Roxburghin DThe biogenetically interesting, octacyclic indole alkaloid roxburghin D can be synthesized stereoselectively from a configuratively pure intermediate. The steric course of the decisive cyclisation reaction is disclosed by means of model substances.
    Notes: Das biogenetisch interessante, octacyclische Indolalkaloid Roxburghin D kann, ausgehend von einem sterisch einheitlichen Zwischenprodukt, stereoselektiv aufgebaut werden. Der sterische Verlauf der entscheidenden Cyclisierungsreaktion wird unter Verwendung von Modellsubstanzen geklärt.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions with Indole Derivatives, XXXVII. Stereoselective Synthesis of Polycyclic Cyclopropane Derivatives in the Indoloquinolizine SeriesThe high yield stereoselective synthesis of the pentacyclic cyclopropanelactam 8 is reported.
    Notes: Es wird über eine in guten Ausbeuten verlaufende stereoselektive Synthese des pentacyclischen Cyclopropanlactams 8 berichtet.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 565-575 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Branched and Chain-Extended Sugars, XXXI. - Synthesis of the Deferri Form of the Oxygen Analogue of δ1-AlbomycinThe oxygen analogue of the deferri form of δ1-albomycin has been synthesized. Reaction of the xylo-dialdehyde 2 with the anion of the lithium salt 3 of N,N-bis(trimethylsilyl)glycine trimethylsilyl ester leads to the chain-extended sugar. In good stereochemical selectivity the desired 6-amino-6-desoxy-L-ido-hepturonic acid is isolated as derivative 8. After transformation of 8 into the 1-acetate 23 the nucleoside 26 is obtained by a modification of the Hilbert-Johnson reaction using the uracil derivative 24. N-Methylation of 26 gives 28 in good yield. The serine derivative 31 reacts with the deblocked amino compound 30 to yield the peptide nucleoside 32. The tripeptide 36, which contains three units of N5-acetyl-N5-hydroxy-L-ornithine, is successfully linked to the partial deblocked compound 34 via the mixed carbonic anhydride method. Final hydrogenation of 37 gives the free deferri form of the oxygen analogue 38.
    Notes: Es wird das Sauerstoffanalogon der Desferriform des δ1-Albomycins synthetisiert. Zum Aufbau des Zuckerteils wird die xylo-Dialdopentofuranose 2 mit dem Anion des Lithiumsalzes 3 von N,N-Bis(trimethylsilyl)glycin-trimethylsilylester umgesetzt. Die gewünschte 6-Amino-6-desoxy-L-glycero-L-ido- heptofuranuronsäure wird mit guter Stereoselektivität gebildet und nach Derivatisierung als Verbindung 8 isoliert. Nach Überführung von 8 in das 1-Acetat 23 ist mit Hilfe der modifizierten Hilbert-Johnson-Methode unter Verwendung des Uracil-Derivates 24 das Nucleosid 26 darstellbar, das zu 28 N-methyliert werden kann. Nach dem Aktivesterverfahren ist nach Freisetzung der Aminogruppe zu 30 eine Anknüpfung des Serin-Derivates 31 zum Peptid 32 möglich. Nach partieller Entblockierung zu 34 gelingt mit der Methode der gemischten Anhydride die Anknüpfung des Tripeptids 36, welches aus drei Einheiten von N5-Acetyl-N5-hydroxy-L-ornithin besteht. Durch Hydrogenolyse ist aus 37 die freie Desferriform des Sauerstoffanalogons 38 erhältlich.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1399-1407 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Albomycins, I. - Enzymatic Cleavage of the Deferri Form of the Albomycins δ1, δ2Enzymatic hydrolyses of albomycin δ2 (1a) were attempted with 23 enzymes or enzyme mixtures. 1a and albomycin δ1 (1b) were cleaved with leucine aminopeptidase (microsomal, hog kidney), subtilisin, aminoacylase I, β-lactamase, proteinase K, and pronase E to give the serine-containing nucleosides 3a and b. With microsomal leucine aminopeptidase a further reaction yields the serine-free nucleosides 4a and b. The hydroxamic acid 6 was also isolated.
    Notes: Enzymatische Hydrolyseversuche an Albomycin δ2 (1a) werden mit 23 Enzymen oder Enzymgemischen durchgeführt. 1a und Albomycin δ1 (1b) werden mit Leucinaminopeptidase (mikrosomal, Schweineniere), Subtilisin, Aminoacylase I, β-Lactamase, Proteinase K und Pronase E zu den serinhaltigen Nucleosiden 3a und b gespalten. Mit der mikrosomalen Leucinaminopeptidase erfolgt eine Weiterreaktion zu den serinfreien Nucleosiden 4a und b. Die Hydroxamsäure 6 konnte ebenfalls rein isoliert werden.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1424-1433 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Albomycins, III. - Synthesis of N5-Acetyl-N5 -hydroxy-L-ornithine from L-Glutamic AcidThe hydroxamic acid N5-acetyl-N5-hydroxy-L-ornithine (2a) is of crucial importance for the biological activity of the siderochromes. L-Glutamic acid (3), a cheap and readily available starting material, can be modified selectively at the γ-carboxylic acid function after protection of the α-amino acid group. An orthogonal protecting group pattern is the precondition for selective cleavages to partially protected amino acids and to the hydroxamic acid 2a.
    Notes: Die Hydroxamsäure N5-Acetyl-N5-hydroxy-L-ornithin (2a) besitzt entscheidende Bedeutung für die biologische Wirkung der Siderochrome. Die preiswerte L-Glutaminsäure (3) kann nach Schutz der α-Aminosäuregruppierung selektiv an der γ-Carbonsäurefunktion derivatisiert werden. Ein orthogonales Schutzgruppenmuster ist Voraussetzung für selektive Spaltungen zu partial geschützten Aminosäuren und zur Hydroxamsäure 2a.
    Type of Medium: Electronic Resource
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  • 7
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Albomycins, II. - Absolute Configuration of the Deferri Form of the AlbomycinsChemical and enzymatic hydrolyses afford the degradation products of the albomycins δ2, δ1, and ε (1a - c). The absolute configuration of these degradation products or of there derivatives could be elucidated by the combination of chiroptical, gaschromatographic, and NMR (NOE) spectroscopic methods. N5-Acetyl-N5-hydroxyornithine (4) and serine (3) exist in the L-configuration, while the nucleoside contains the 6-amino-6-deoxy-4-thio-L-glycero-α-L-ido-heptofuranuronic acid. The configuration of this nucleoside could also be established by the X-ray analysis of the sulfoxide 21.
    Notes: Chemische und enzymatische Hydrolysen führen zu Abbauprodukten der Albomycine δ2, δ1 und ε (1a - c). Die absoluten Konfigurationen der Abbauprodukte oder deren Derivate werden durch Kombination chiroptischer, gaschromatographischer und NMR-spektroskopischer (NOE) Methoden abgeleitet. N5-Acetyl-N5-hydroxyornithin (4) und Serin (3) liegen in der L-Konfiguration vor, während das Nucleosid die 6-Amino-6-desoxy-4-thio-L-glycero-α-L-ido-heptofuranuronsäure enthält. Die Konfiguration des Nucleosids wird unabhängig davon durch die Röntgenstrukturanalyse des kristalline Sulfoxids 21 belegt.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 8
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 103 (1991), S. 1735-1737 
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 9
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: No Abstract.Das vollständige Manuskript dieser Zuschrift erscheint in: Angew. Chem. Suppl. 1982, 1322-1335
    Type of Medium: Electronic Resource
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  • 10
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Albomycins, IV. - Isolation and Total Synthesis of (N5-Acetyl-N5 -hydroxy-L-ornithyl)-(N5 -acetyl-N5-hydroxy-L-ornithyl)-N5 -acetyl-N5 -hydroxy-L-ornithineThe isolation, characterization, and synthesis of the oligopeptide (N5-acetyl-N5-hydroxy-L-ornithyl)-(N5-acetyl-N5-hydroxy-L-ornithyl)-N5-acetyl-N5-hydroxy-L-ornithine (2), the hydroxamic acid side-chain of the albomycins, is described.
    Notes: Die Isolierung, Charakterisierung und Synthese von (N5-Acetyl-N5-hydroxy-L-ornithyl)-(N5-acetyl-N5-hydroxy-L-ornithyl)-N5-hydroxy-L-ornithin (2), der Hydroxamsäureseitenkette der Albomycine wird beschrieben.
    Type of Medium: Electronic Resource
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