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  • Chemistry  (6)
  • General Chemistry  (6)
  • 2000-2004  (6)
  • 1
    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.
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  • 2
    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.
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  • 3
    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.
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  • 4
    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.
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  • 5
    Electronic Resource
    Electronic Resource
    Structural Diversity of 1-O-Acyl α-L-Rhamnopyranosides by Precursor-Directed Biosynthesis with Streptomyces griseoviridis (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1875-1881 
    Details
    ISSN: 1434-193X
    Keywords: Metabolism ; Biosynthesis ; Glycosides ; Carbohydrates ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The ability of Streptomyces griseoviridis (strain Tü 3634) to glycosylate various carboxylic acids with L-rhamnose was investigated by feeding mainly heteroaromatic and aromatic carboxylic acids to growing cultures. The special application of the precursor-directed biosynthesis (PDB) gave rise to a wide variety of acyl α-L-rhamnopyranosides as novel metabolites. The experiments resulted in furanyl, pyrrolyl, thienyl, indolyl, and pyridyl derivatives (1-8), the analogues 9-24 were generated by feeding fluoro-, hydroxy- or aminobenzoic acids or cinnamic acids. All results are discussed with respect to the substrate specificity of the corresponding enzyme system.Supporting information for this article is available on the WWW under //http://www.wiley-vch.de/contents/jc_2046/2000/99567_s.pdf or from the author.
    Additional Material: 3 Tab.
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  • 6
    Electronic Resource
    Electronic Resource
    Biosynthesis of Gabosines A, B, and C, Carba Sugars from Streptomyces cellulosae (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1883-1887 
    Details
    ISSN: 1434-193X
    Keywords: Biosynthesis ; Gabosine ; Bioorganic chemistry ; Carbohydrates ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The biosynthesis of the gabosines A-C (3-5) was studied by feeding cultures of Streptomyces cellulosae subsp. griseorubiginosus (strain S 1096) with 13C-labeled precursors. Although the carba sugars are structurally related to shikimic acid, the biosynthetic origin was found to be different to the shikimate pathway. The results revealed that the gabosines are formed via a pentose phosphate pathway by cyclization of a heptulose phosphate intermediate. This intermediate arises from a triose phosphate by successive transfer of two C2 fragments by transketolases. This pathway is identical as that described for valienamine (7), the aminocarba sugar moiety of validamycin, and acarbose (2). The results from biosynthetic studies are discussed on the background of the variety of gabosines found in nature.
    Additional Material: 2 Tab.
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