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Scytalidamides A and B, New Cytotoxic Cyclic Heptapeptides from a Marine Fungus of the Genus Scytalidium

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    Scytalidamides A and B, New Cytotoxic Cyclic Heptapeptides from a Marine Fungus of the Genus Scytalidium
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    Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, La Jolla, California 92093-0204
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2003, 68, 23, 8767–8773
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    https://doi.org/10.1021/jo030191z
    Published October 14, 2003
    Copyright © 2003 American Chemical Society
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    Abstract

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    Two new cyclic heptapeptides have been isolated from the culture broth of a marine fungus, Scytalidium sp., collected from the Bahamas. The planar structures of scytalidamides A (1) and B (2) were assigned on the basis of 1D and 2D NMR spectroscopic techniques, while the absolute configuration of the amino acid residues in both molecules was determined by application of the advanced Marfey's method. The absolute stereochemistry of the uncommon 3-methylproline moiety in scytalidamide B (2) was confirmed by isolation and CD measurements, as well as application of the advanced Marfey's method. Scytalidamides A (1) and B (2) showed moderate in vitro cytotoxicity toward HCT-116 human colon adenocarcinoma with IC50 values of 2.7 and 11.0 μM, respectively.

    Copyright © 2003 American Chemical Society

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    1D and 2D NMR spectra of 1 and 2; 1H NMR and CD spectra of (2S,3S)-3MePro. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Org. Chem. 2003, 68, 23, 8767–8773
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo030191z
    Published October 14, 2003
    Copyright © 2003 American Chemical Society
    Request reuse permissions

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