Revised absolute stereochemistry of natural kulokekahilide-2

Yuuki Takada, Masahiro Umehara, Youichi Nakao, Junji Kimura

    Research output: Contribution to journalArticle

    18 Citations (Scopus)

    Abstract

    Kulokekahilide-2 is a potent cytotoxic depsipeptide isolated from the Hawaiian marine mollusk Philinopsis speciosa. The structure of kulokekahilide-2 was reported to be composed of five amino acids (l-Ala, l-Ile, MeGly, l-MePhe, d-Ala) and two hydroxy acids (d-Hica, 5S,6S,7S-Dtda); however, following its total synthesis, the 1H NMR spectrum of the synthetic compound was found to be different from that of the natural one, suggesting that the stereochemistry of the reported structure was incorrect. To determine the stereochemistry of the natural compound, arrays of analogues have been prepared using different sets of chiral amino acids, and the absolute stereochemistry of kulokekahilide-2 has been unambiguously confirmed to involve the combination 21-l-Ala, 24-d-MePhe, and 43-d-Ala.

    Original languageEnglish
    Pages (from-to)1163-1165
    Number of pages3
    JournalTetrahedron Letters
    Volume49
    Issue number7
    DOIs
    Publication statusPublished - 2008 Feb 11

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    Stereochemistry
    Depsipeptides
    Amino Acids
    Hydroxy Acids
    Mollusca
    Nuclear magnetic resonance
    kulokekahilide-2

    Keywords

    • cis-trans Conformations
    • Cytotoxicity
    • Kulokekahilide-2
    • Macrolactamization

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Revised absolute stereochemistry of natural kulokekahilide-2. / Takada, Yuuki; Umehara, Masahiro; Nakao, Youichi; Kimura, Junji.

    In: Tetrahedron Letters, Vol. 49, No. 7, 11.02.2008, p. 1163-1165.

    Research output: Contribution to journalArticle

    Takada, Yuuki ; Umehara, Masahiro ; Nakao, Youichi ; Kimura, Junji. / Revised absolute stereochemistry of natural kulokekahilide-2. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 7. pp. 1163-1165.
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