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  • 11
    Electronic Resource
    Electronic Resource
    Identification of oestrogen metabolites in human urine by capillary gas chromatography and mass spectrometry (1989)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 18 (1989), S. 87-95 
    Details
    ISSN: 0887-6134
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oestrogen metabolites from the urine of males and pregnant and non-pregnant females were enriched by a procedure involving column chromatography on adsorber resins, gels and ion exchangers, enzymatic solvolysis and extraction, thereby separating the oestrogens from most of the interfering material. After derivatization of the oestrogens as their trimethylsilyl ethers profiles were measured with a fused silica column and a flame ionization detector by gas chromatography. Using a combination of capillary gas chromatography and mass spectrometry approximately 50 oestrogen metabolites were detected in the human urine of males and females, of which 19 were unknown urine compounds. Not all could be identified definitely owing to the lack of reference material. Mass spectra of trimethylsilylated oestrogens with functional groups at position 11 (11-dehydroestradiol, 11-dehydroestrone and 11β-hydroxyestrone) were discussed in their common and discernible fragmentations.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bms.1200180202
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  • 12
    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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  • 13
    Electronic Resource
    Electronic Resource
    Secondary Metabolites by Chemical Screening, 34. - Aspinolides and Aspinonene/Aspyrone Co-Metabolites, New Pentaketides Produced by Aspergillus ochraceus (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 87-95 
    Details
    ISSN: 0947-3440
    Keywords: Aspinolides ; Aspinonene ; Aspyrone co-metabolites ; Aspergillus ; Pentaketides ; Lactones ; Metabolism ; Natural products ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New 10-membered lactones, named aspinolide A-C (3, 4, 5), and the aspinonene/aspyrone co-metabolites, named trienediol (6), isoaspinonene (7), dihydroaspyrone (8), and dienetriol 9 were discovered by chemical screening methods in the cultures of Aspergillus ochraceus (DSM-7428) under altered fermentation conditions. The structures were established by detailed spectroscopic analysis. The polyketide origin of the skeleton and the biogenesis of the oxygen atoms were verified by feeding sodium [1,2-13C2]acetate and [18O2] gas, respectively, to growing cultures of the fungus. A comprehensive discussion of the supposed biosynthetic pathways draws the conclusion that two polyketide synthases (PKSα, PKSβ) exist, forming two different series of pentaketides in parallel. One pathway leads to branched-chain metabolites by a Favorski-like rearrangement of an epoxide intermediate, while the other involves detachment of the pentaketides from the PKSβ by lactonisation without any rearrangement of the carbon skeleton. The former pathway is affected by an inhibitor of cytochrome P450 dependent monooxygenases.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970114
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  • 14
    Electronic Resource
    Electronic Resource
    Structural and Biosynthetic Investigations of the Rubromycins (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 729-735 
    Details
    ISSN: 1434-193X
    Keywords: Rubromycins ; Natural products ; Biosynthesis ; Quinones ; Structure elucidation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The structure of the known secondary metabolite β-rubromycin was corrected, based on spectroscopic and chemical investigations, from o-quinone 1 to p-quinone 6. By feeding [U-13C3]malonic acid to the rubromycin-producing strain, Streptomyces sp. A1, the polyketide origin of the skeleton was verified, but the identity of the starter unit and the folding mechanism of the polyketide chain are still unclear. From the culture broth of the strain A1, in addition to 6, the co-metabolites γ-rubromycin (3), δ-rubromycin (4) and 3′-hydroxy-β-rubromycin (7) were isolated. Their structures were determined or confirmed by detailed spectroscopic analysis. The rubromycins inhibit HIV-1 reverse transcriptase (RT) and are cytostatically active against different tumor cell lines.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 15
    Electronic Resource
    Electronic Resource
    Structure and Biosynthesis of Mutolide, a Novel Macrolide from a UV Mutant of the Fungus F-24′707 (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1451-1456 
    Details
    ISSN: 1434-193X
    Keywords: Mutolide ; Metabolites, secondary ; Macrolide ; Chemical screening ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The 14-membered macrolide, mutolide (1), was discovered by chemical screening of the culture broth of the fungus F-24′707y, obtained after UV mutagenesis of the wild type strain, which normally produces the spirobisnaphthalene cladospirone bisepoxide (2). The structure of 1 was established by detailed spectroscopic analysis, X-ray analysis and derivatisation. The biogenetic origin of the carbon skeleton and the hydroxy groups was verified by feeding sodium [1-13C]acetate and 18O2 to growing cultures of the fungus. Macrolide 1 is generated from acetate/malonate only. The unexpected change of the normal metabolite pattern of this strain is discussed, and proves the value of the OSMAC method.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 16
    Electronic Resource
    Electronic Resource
    Acyl α-L-Rhamnopyranosides, a Novel Family of Secondary Metabolites from Streptomyces sp.: Isolation and Biosynthesis (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 929-937 
    Details
    ISSN: 1434-193X
    Keywords: α-L-Rhamnopyranosides ; Secondary metabolites ; Biosynthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---In the course of our chemical screening program, the novel acyl α-L-rhamnopyranosides (1-6) were detected as metabolites from five different strains of Streptomycetes. The structures of all these compounds were elucidated by chemical and spectroscopic methods. The biosynthesis of 1 and 3 was established by feeding 13C-labelled acetate, glycerol, and D-glucose to Streptomyces griseoviridis (strain Tü 3634), and resulted in a complete labelling pattern of the 2,4-dimethyl-3-furanylcarbonyl and benzoyl residues, as well as the rhamnose moiety. These results reveal biosynthetic pathways of general importance and give an insight into the generation of the hexose phosphates, from which deoxysugars are formed. The acyl rhamnosides are members of a novel family of microbial metabolites and are considered as rhamnoconjugates from Streptomycetes.Supporting information for this article is available on the WWW under //http://www.wiley-vch.de/contents/jc_2046/2000/99413_s.pdf or from the author.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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  • 17
    Electronic Resource
    Electronic Resource
    Gabosines L, N and O: New Carba-Sugars from Streptomyces with DNA-Binding Properties (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 149-153 
    Details
    ISSN: 1434-193X
    Keywords: Gabosine ; Secondary metabolite ; Carbohydrates ; Chemical screening ; Biomolecular-chemical screening ; DNA binding ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---In addition to the known gabosines A (4), B (5) and C (6), three new gabosines L (1), N (2) and O (3) were detected by chemical screening as secondary metabolites of Streptomyces (strains GT 041230, GT 051024 and S 1096). The constitutions of 1, 2 and 3 were established by spectroscopic techniques and derivatization reactions. The absolute stereochemistry of 1 and 2 was determined by Helmchen's method and has been verified in the case of gabosine N (2) by X-ray analysis. The DNA-binding properties of the gabosines were investigated and analyzed by binding studies using a recently developed thin-layer chromatography technique (bimolecular-chemical screening).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 18
    Electronic Resource
    Electronic Resource
    Oxidations- und Eliminierungsreaktionen am Diazomethan-Addukt von Bi-2,2′-(1,4-naphthochinon) (1967)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 79 (1967), S. 477-477 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19670791017
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  • 19
    Electronic Resource
    Electronic Resource
    Organisch-chemisches Praktikum Für Chemiker, Biologen, Pharmazeuten und Mediziner. Von G. Kempter. Friedr. Vieweg & Sohn, Wiesbaden, 3. Aufl. 1978, 268 S., 96 Abb., 25 Tab., Paperback DM 24,80 (1979)
    Weinheim : Wiley-Blackwell
    Chemie in unserer Zeit 13 (1979), S. 95-95 
    Details
    ISSN: 0009-2851
    Keywords: Chemistry ; Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ciuz.19790130308
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  • 20
    Electronic Resource
    Electronic Resource
    Secondary Metabolites by Chemical Screening, 36Part 35. Ref.[1].. Ulupyrinone and Ulufuranol: New Heteroaromatic Metabolites from Streptomyces spina (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 937-939 
    Details
    ISSN: 0947-3440
    Keywords: Ulupyrinone ; Ulufuranol ; Metabolism ; Chemical screening ; Streptomyces ; Structure elucidation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chemical Screening with extracts of Actinomycetes strains resulted in the detection, isolation, and structural elucidation of two new heteroaromatic secondary metabolites, named ulupyrinone (1) and ulufuranol (2), from Streptomyces spina (strain FH-S 2144). The absolute configuration of ulufuranol (2) was determined by analysis of the CD spectra of its dibenzoate, 3, using the dibenzoate chirality rule.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970523
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