Oligo(4-aminopiperidine-4-carboxylic acid): An unusual basic oligopeptide with an acid-induced helical conformation

Joon Il Cho, Masahiro Tanaka, Sota Sato, Kazushi Kinbara, Takuzo Aida

    Research output: Contribution to journalArticle

    23 Citations (Scopus)

    Abstract

    In sharp contrast with helical polypeptides carrying basic side chains, Api8, a basic oligopeptide containing the non-natural achiral amino acid 4-aminopiperidine-4-carboxylic acid (Api), adopts a helical conformation only in acidic media. Alkaline titration of a protonated Api8 oligomer appended with a leucine derivative at its N-terminus showed that disruption of its helical conformation occurs in a pH range of 7-10. NMR studies indicated that the piperidine groups in Api8, when nonprotonated, possibly interact with the proximal amide protons in the peptide backbone and hamper the formation of the H-bonding network responsible for the helical conformation. The helical structure is induced not only by protonation but also by acylation of the piperidine groups.

    Original languageEnglish
    Pages (from-to)13176-13178
    Number of pages3
    JournalJournal of the American Chemical Society
    Volume132
    Issue number38
    DOIs
    Publication statusPublished - 2010 Sep 29

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)
    • Biochemistry
    • Colloid and Surface Chemistry

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