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Lyngbyastatin 1 and Ibu-epilyngbyastatin 1: Synthesis, stereochemistry, and NMR line broadening

  1. Author:
    Bai, R. L.
    Bates, R. B.
    Hamel, E.
    Moore, R. E.
    Nakkiew, P.
    Pettit, G. R.
    Sufi, B. A.

  2. Author Address

    Univ Arizona, Dept Chem, Tucson, AZ 85721 USA Univ Arizona, Dept Chem, Tucson, AZ 85721 USA NCI, Screening Technol Branch, Dev Therapeut Program, Div Canc Treatment & Diagnosis,NIH, Frederick, MD 21702 USA Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA Arizona State Univ, Canc Res Inst, Tempe, AZ 85287 USA Arizona State Univ, Dept Chem, Tempe, AZ 85287 USA Bates RB Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
    1. Year: 2002
  2. Journal: Journal of Natural Products
    1. 65
    2. 12
    3. Pages: 1824-1829
  4. Type of Article: Article
  1. Abstract:

    The synthesis of a lyngbyastatin 1-Ibu-epilyngbyastatin 1 mixture combined with NMR and molecular modeling studies proved that natural lyngbyastatin 1 was only one Ibu epimer rather than a mixture of both and that the configuration of this epimer in the Ibu unit was R. The substance isolated with lyngbyastatin 1 was Ibu-epidolastatin 12. The extreme broadness in the proton NMR spectra of lyngbyastatin 1 and Ibu- epidolastatin 12 was exchange broadening due to rotation about the Ibu-Ala amide bond. It was a consequence of (1) a small energy difference between the cis and trans forms of this bond, (2) a substantial difference in conformation between these forms, and (3) a lowered barrier between them compared to most amide bonds (due to steric hindrance). The synthetic lyngbyastatin 1-Ibu-epilyngbyastatin 1 mixture had significant activities against cancer cells and in stimulating actin polymerization, but was less active than dolastatin 11 in all assays.

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