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  • Gabosine  (3)
  • Metabolism  (3)
  • Wiley-Blackwell  (6)
  • Springer
  • 1
    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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  • 2
    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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  • 3
    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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  • 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.
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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.
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  • 6
    Electronic Resource
    Electronic Resource
    Secondary Metabolites by Chemical Screening, 22. Gabosines, New Carba-sugars From Streptomyces (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 241-250 
    Details
    ISSN: 0170-2041
    Keywords: Gabosine ; Metabolites, secondary ; Streptomyces ; Carba-sugar ; Chemical screening ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chemical screening of different Streptomycetes strains resulted in the detection, isolation, and structure elucidation of a number of novel carba-sugars. The constitution of these secondary metabolites, named gabosines A to K (1 to 11), was deduced from spectroscopic data as well as chemical transformation reactions. The gabosines exhibit a basic C7 skeleton and can be characterized as hydroxylated branched cyclohexanone derivatives, which show structural similarities to carbohydrates deriving from secondary metabolism. The configuration fo the gabosines (absolute stereochemistry for 1, 4, 5, and 6; relative configuration for the remaining metabolites) was determined by derivatization with chiral acids (Helmchen's method), NMR spectral analysis, as well as by a comparison of optical rotation values with those of the already known gabosines B (2) and C (3). The new term “ketocarbasugars” is used to characterize a typical ketone containing subgroup of carba-sugars originating from microbial sources. The well available natural gabosines can be used as suitable chiral building blocks.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930143
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