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  • Isolation and Structure Elucidation of the New Fungal Metabolite (-)-Xylariamide A

    Author(s)
    Davis, RA
    Griffith University Author(s)
    Davis, Rohan A.
    Year published
    2005
    Metadata
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    Abstract
    Chemical investigations of the terrestrial microfungus Xylaria sp. have afforded the new natural product (-)-xylariamide A (1). The gross structure of 1 was determined by interpretation of 1D and 2D NMR, UV, IR and MS data. Confirmation of the structure and the absolute stereochemistry of 1 were determined by the total synthesis of (+)-xylariamide A (2). Synthetic 2 was produced by N,O-bis(trimethylsilyl)acetamide induced coupling of 3-chloro-L-tyrosine (3) with (E)-but-2-enedioic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester (4). Optical rotation comparison of 1 with 2 indicated that the natural product (1) contained ...
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    Chemical investigations of the terrestrial microfungus Xylaria sp. have afforded the new natural product (-)-xylariamide A (1). The gross structure of 1 was determined by interpretation of 1D and 2D NMR, UV, IR and MS data. Confirmation of the structure and the absolute stereochemistry of 1 were determined by the total synthesis of (+)-xylariamide A (2). Synthetic 2 was produced by N,O-bis(trimethylsilyl)acetamide induced coupling of 3-chloro-L-tyrosine (3) with (E)-but-2-enedioic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester (4). Optical rotation comparison of 1 with 2 indicated that the natural product (1) contained 3-chloro-D-tyrosine. Both enantiomers of xylariamide A were tested in a brine shrimp lethality assay and only the natural product (1) showed toxicity.
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    Journal Title
    Journal of Natural Products
    Volume
    68
    Publisher URI
    http://pubs.acs.org/journal/jnprdf
    DOI
    https://doi.org/10.1021/np050025h
    Copyright Statement
    © 2005 American Chemical Society. Self-archiving of the author-manuscript version is not yet supported by this publisher.
    Subject
    Chemical sciences
    Biological sciences
    Biomedical and clinical sciences
    Publication URI
    http://hdl.handle.net/10072/4982
    Collection
    • Journal articles

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