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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
    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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  • 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.
    Type of Medium: Electronic Resource
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  • 4
    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.
    Type of Medium: Electronic Resource
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  • 5
    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.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    The chemistry of unusual macrolides, 2. Spectroscopic and biosynthetic investigations of the V-type ATPase inhibitor concanamycin A (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 305-312 
    Details
    ISSN: 0170-2041
    Keywords: Concanamycin A ; Macrolides ; Biosynthesis ; Polyketide ; Conformational studies ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 1H- and 13C-NMR spectra of the conformationally flexible macrolide concanamycin A (1) have been assigned by the use of 2D NMR techniques at low temperatures and have enabled biosynthetic studies on this most potent inhibitor of vacuolar ATPases. By feeding of different [13C]-labeled precursors to Streptomyces sp. (strain Gö 22/15) the polyketide origin of the concanamycin skeleton was proved. It arises from a tetradecaketide, which is based on four acetate and seven propionate units besides one butyrate and two unusual C2 building blocks from the triose pool. In combination with former findings it is possible to predict the biogenetic assembly of several strongly related unusual macrolides, for which the group name “plecomacrolides” should be used in future. The results are discussed in the light of modern hypothesis as stated for polyketide pathways.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940313
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