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  • 1
    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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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1875-1881 
    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
    Library Location Call Number Volume/Issue/Year Availability
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