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  • 1
    Electronic Resource
    Electronic Resource
    Metabolic products of microorganisms, 271. Momofulvenone A and B, new benzo[b]fluorene quinones from Streptomyces (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1169-1172 
    Details
    ISSN: 0947-3440
    Keywords: Momofulvenone ; Metabolites, secondary ; Benzo[b]fluorene quinone ; Biosynthesis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: From the cultures of Streptomyces diastatochromogenes (strain Tü 2895) two novel benzo[b]fluorene quinones, named momofulvenone A (1) and B (2), were isolated. Difficulties in their spectroscopic characterization due to salt effects were overcome by fermentation in the presence of ammonium acetate. The structures were established by a detailed spectroscopic analysis. The polyketide origin of 1 and 2 was verified by feeding [1,2-13C2]acetate to the growing cultures of Tü 2895. The momofulvenones represent the nitrogen-free parent compound of the kinamycin family of antibiotics.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199507158
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  • 2
    Electronic Resource
    Electronic Resource
    3.3′(5.5′)-Bipyrazolyl-Derivate durch Oxydation des Diazomethan-Adduktes von Bis-[naphthochinon-(1.4)-yl-(2)] (1967)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 100 (1967), S. 2885-2898 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Durch Oxydation des Diazomethan-Adduktes von Bis-[naphthochinon-(1.4)-yl-(2)] (1) entsteht neben Benz[f]indazol-chinon-(4.9) (3a) 4.4′-Bis-[2-carboxy-benzoyl]-bipyrazolyl-(3.3′(5.5′)) (5a); das Ausbeuteverhältnis hängt weitgehend von der Art des Oxydationsmittels ab.  -  5a zeigt Ring-Ketten-Tautomerie und läßt sich in beiden Molekülhälften zu einem Lacton (6c) und einem cyclischen Äther (8) reduzieren.  -  Alkalischmelze von 5a liefert Benzoesäure und 4.4′-Dicarboxy-bipyrazolyl-(3.3′(5.5′)) (11a), das leicht zu Bipyrazolyl-(3.3′(5.5′)) (12) decarboxyliert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19671000913
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  • 3
    Electronic Resource
    Electronic Resource
    Zur Tautomerie des Actinorhodins und 2.2′-Binaphthazarins (1968)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 101 (1968), S. 4221-4229 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Durch NMR-spektroskopischen Vergleich mit Modellverbindungen wird bewiesen, daß von den zehn formal möglichen Tautomeren des Actinorhodins in Lösung ganz überwiegend 2a vorliegt und daß Acetylierung von Actinorhodin-dimethylester sowie 2.2′-Binaphthazarin nur das Tetraacetat 2b bzw. 3b des Tautomeren 2c bzw. 3a liefert. - Im Gegensatz zur Methylierung wird die Acetylierung kernsubstituierter Naphthazarine thermodynamisch gelenkt und gibt daher das Acetat des in Lösung dominierenden Tautomeren.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19681011222
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  • 4
    Electronic Resource
    Electronic Resource
    Rubromycine, II (1969)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 102 (1969), S. 126-151 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Die Isolierung der roten Antibiotica β-Rubromycin und γ-Rubromycin wird beschrieben. - β-Rubromycin isomerisiert sich in siedendem Pyridin quantitativ zu α-Rubromycin und wird durch verd. Mineralsäuren unter Verseifung eines Methoxyls in γ-Rubromycin verwandelt. γ-iso-Rubromycin entsteht: 1. Aus γ-Rubromycin durch Erhitzen mit Pyridin oder konz. Schwefelsäure, 2. aus α-Rubromycin durch Chlorwasserstoff in Chloroform. - β-Rubromycin (11) enthält als Chromophor 8-Hydroxy-5.7-dimethoxy-naphthochinon-(1.2), das über Sauerstoff an C-4 und eine Methylengruppe an C-3 mit dem Rest des Moleküls verbunden ist. - Chromophor der drei anderen Rubromycine (12, 13, 14a) ist 5.8-Dihydroxy-2(bzw. 7)-methoxy-naphthochinon-(1.4) - in α-Rubromycin am 5-Hydroxyl methyliert -, an dem über Sauerstoff an C-7 (bzw. C-2) und Kohlenstoff an C-6 (bzw. C-3) der Rest des Moleküls hängt.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19691020118
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  • 5
    Electronic Resource
    Electronic Resource
    Rubromycine, III. Die Konstitution von α-Rubromycin, β-Rubromycin, γ-Rubromycin und γ-iso-Rubromycin (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 1709-1726 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Rubromycins, III. The Constitution of α-Rubromycin, β-Rubromycin, γ-Rubromycin, and γ-iso-RubromycinAlkalihydroxide isomerizes the antibiotics β-rubromycin and γ-rubromycin by way of intramolecular β-elimination to α-rubromycin and γ-iso-rubromycin, respectively, and cleaves these under forcing conditions to 5a, 15a, 16a and 18a. Thereby the partial γ-iso-rubromycin structure 4 leads to the total structure 25a, similarly, 3 leads to 24. In both compounds an ethylene group connects a naphtho[2,3-b]furanoquinone-(4,9) chromophore at C-2 with that of a 7,8-dihydroxy-3-methoxycarbonylisocoumarin at C-6′. Compounds 24 and 25a as well as the rearrangement scheme 1-4 give rise to β-rubromycin (22) and γ-rubromycin (23a); in antibiotically active rubromycins a spiroketal system connects the naphthoquinone chromophore with that of the isocoumarin residue.
    Notes: Alkalihydroxid isomerisiert die Antibiotica β-Rubromycin und γ-Rubromycin durch intramolekulare β-Eliminierung zu α-Rubromycin bzw. γ-iso-Rubromycin und spaltet diese unter energischen Bedingungen in 5a, 15a, 16a und 18a. Damit wird aus der γ-iso-Rubromycin-Teilformel 4 die Konstitutionsformel 25a und aus 3 die α-Rubromycin-Formel 24; in beiden Verbindungen ist ein Naphtho[2.3-b]furanochinon-(4.9)-Chromophor in 2-Stellung über eine Äthylengruppe mit C-6′ eines 7.8-Dihydroxy-3-methoxycarbonyl-isocumarin-Restes verbunden. Aus 24, 25a sowie dem Umlagerungsschema 1-4 ergibt sich 22 für β-Rubromycin und 23a für γ-Rubromycin; in den antibiotisch wirksamen Rubromycinen verbindet ein Spiroketal-System den Naphthochinon-Chromophor mit dem Isocumarin-Rest.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030607
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  • 6
    Electronic Resource
    Electronic Resource
    Stoffwechselprodukte von Mikroorganismen, 172. Isolierung des Antibioticums semi-Vioxanthin aus Penicillium citreo-viride und Synthese des Xanthomegnins (1979)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 957-978 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Metabolic Products of Microorganism, 172. Isolation of the Antibiotic semi-Vioxanthin from Penicillium citreo-viride and Synthesis of XanthomegninBesides xanthomegnin (16 b), 3,4-dehydroxanthomegnin (29a), viomellein (23) and vioxanthin (3) from Penicillium citreo-viride under different culture conditions semi-vioxanthin (7) was isolated. Structure 7 has been established by its spectra and the fact that oxidation with Fremy's salt gives 3,4,6,9-tetrahydro-10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-1H-naphtho[2,3-c]pyran (9a = semi-xanthomegnin). -9c, prepared by demethylation of 9a, was dimerized by potassium peroxydisulfate/sodium hydroxide and methylated, giving 16b. Synthetic 16b and authentic xanthomegnin were identical, which verifies the structure revised by Höfle and Röser9) and shows, that the dyes of the xanthomegnin series are biogenetically homogenous. - The metabolic products of the strain inhibit the growth of bacteria. 16b and 26 furthermore have an effect against insects.
    Notes: Neben Xanthomegnin (16b), 3,4-Dehydroxanthomegnin (29 a), Viomellein (23) und Vioxanthin (3) wurde aus Penicillium citreo-viride unter veränderten Kulturbedingungen semi-Vioxanthin (7) isoliert. Konstitution 7 folgt aus den Spektren und dem Befund, daß mit Fremy-Salz 3,4,6,9-Tetrahydro-10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-1H-naphtho[2.3-c]pyran (9a = semi-Xanthomegnin) entsteht. - Das durch Entmethylierung von 9a zugängliche 9c ließ sich mit Kaliumpersulfat/Natriumhydroxid zu 16a dimerisieren, das zu 16b methyliert wurde. Synthetisches 16b war mit nativem Xanthomegnin identisch, was die von Höfle und Röser9) revidierte Konstitution bestätigt und beweist, daß die Farbstoffe der Xanthomegnin-Reihe biogenetisch einheitlich sind. - Die Stoffwechselprodukte des Stammes hemmen das Wachstum von Bakterien, 16b und 23 wirken ferner gegen Insekten.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19791120319
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  • 7
    Electronic Resource
    Electronic Resource
    Metabolic products of microorganisms. Part 262Part 261: [1].. The absolute configuration of sphydrofuran, a widespread metabolite from streptomycetes (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1281-1286 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Sphydrofuran (1) was isolated from the culture filtrate of Streptomyces sp. (strain Gö 28 and Tü 3616) by chemical screening methods. Metabolite 1 is an anomeric and ring-chain tautomeric mixture and could easily be transformed into the stable furan derivative 2 under acidic conditions. The constitution and relative configuration of 1 was established by X-ray crystallography of its 8-O-methyl derivative 3a. The absolute configuration at C(4) of 1 and thus of the whole molecule (3R,4S,5S) could be determined starting from 2 using the Helmchen method.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740617
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  • 8
    Electronic Resource
    Electronic Resource
    Stoffwechselprodukte von Mikroorganismen. 253. Mitteilung252, Mitteilung. Hormaomycin, ein neues Peptid-lacton mit morphogener Aktivität auf Streptomyceten (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 426-437 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Hormaomycin, a Novel Peptide Lactone with Morphogenetic Activity on StreptomycesA culture identified as Streptomyces griseoflavus (strain W-384) has been found to produce a novel peptide-lactone antibiotic designated hormaomycin (6). The empirical molecular formula of the compound is established to be C55H69ClN10O14. The constituent amino acids of the antibiotic are suggested to be allothreonine (1; 1), isoleucine (2; 1), 3-methyl-phenylalanine (3; 2), and, for the first time identified from a natural source, 4-[(Z)-prop-1-enyl]-proline (4; 1) and 3-(2-nitrocyclopropyl)-alanine (5; 2). The amino acids were delivered by acidic hydrolysis and assigned by high-resolution- GC/MS analysis (after transformation to derivatives) in combination with extended 2D-NMR experiments of the antibiotic itself. From the latter, it became plausible that the N-terminus of the peptide chain is acylated by a Cl-containing derivative of 1H-pyrrol-2-carboxylic acid. Hormaomycin is active against some Gram-positive bacteria. In addition, the antibiotic exhibits potent aerial mycelium-inducing activity and effects the production of antibiotics.
    Notes: No abstract.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720303
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  • 9
    Electronic Resource
    Electronic Resource
    Secondary metabolites by chemical screening, 10. Glycerinopyrin, a novel metabolite from Streptomyces violaceus (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 77-80 
    Details
    ISSN: 0170-2041
    Keywords: Streptomyces violaceus ; Chemical screening ; 2-Pyrrolecarboxylic acid derivatives ; Glycerol ester, NMR assignments ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Glycerinopyrin (1) was detected by chemical screening as a new metabolite from Streptomyces violaceus. Its structure was elucidated by chemical and spectroscopical methods as (2S)- 2,3-dihydroxypropyl 1-hydroxy-4-methyl-2-pyrrolecarboxylate.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199119910114
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  • 10
    Electronic Resource
    Electronic Resource
    Sekundärstoffe aus dem chemischen Screening, 16. Inthomycine, neue Oxazol-triene aus Streptomyces sp. (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 367-373 
    Details
    ISSN: 0170-2041
    Keywords: Inthomycins ; Metabolites, secondary ; Streptomyces sp. ; Oxazole-triene ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Secondary Metabolites by Chemical Screening, 161). - Inthomycins, New Oxazole-Trienes from Streptomyces sp.The oxazole-triene metabolites inthomycin A to C (2, 4, 6) have been discovered by chemical screening in the culture broth of Streptomyces sp. (strain Gö 2). Its separation was successful only when the compounds had previously been transformed into the 3-O-(S)-2-phenylbutanoates 3, 5 and 7. The structures were deduced from their spectroscopic data, especially those taken from 2D-NMR spectra. The natural products reveal differences in the (E/Z) configuration of its triene chains. By feeding [1-13C]acetate to growing cultures of strain Gö 2, it was determined that C-1 to C-10 of the inthomycins biosynthetically originated via the polyketide pathway. Inthomycin A (2) has already been known as a substructure element of oxazolomycin (1) and probably is identical with the recently described phthoxazolin.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199119910164
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