The effect of sulfur stereochemistry of l-β,β-dimethylmethionine S-oxide on the physicochemical properties of truncated polytheonamides

Shigeru Matsuoka, Yuki Mizoguchi, Hiroaki Itoh, Ken Okura, Naoki Shinohara, Masayuki Inoue

    Research output: Contribution to journalArticle

    12 Citations (Scopus)

    Abstract

    L-β,β-Dimethylmethionine S-oxide is a unique amino acid found in polytheonamides. Four designed hexapeptides containing the sulfide, (S R)-sulfoxide, (SS)-sulfoxide, and sulfone derivatives of l-dimethylmethionine were synthesized and functionally analyzed. Our results indicate that the sulfoxide stereochemistry of the peptides controls their overall physicochemical properties.

    Original languageEnglish
    Pages (from-to)4644-4647
    Number of pages4
    JournalTetrahedron Letters
    Volume51
    Issue number35
    DOIs
    Publication statusPublished - 2010 Sep 1

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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