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    J Org Chem. 2008 Sep 19;73(18):7342-4. Epub 2008 Aug 22.

    THAL, a sterically unhindered linker for the solid-phase synthesis of acid-sensitive protected peptide acids.

    Source

    Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain.

    Abstract

    The 5-(4-hydroxyphenyl)-3,4-ethylenedioxythienyl alcohol (THAL, Thiophene Acid Labile) is described as a new linker for the solid-phase synthesis of peptide carboxylic acids. It is based on the electron-rich 3,4-ethylenedioxythenyl (EDOTn) moiety and allows the obtention of free and tert-butyl-protected peptides by cleavage with 90% and 0.5% TFA, respectively. This very high acid lability makes it useful for the synthesis of sensitive peptides. Free and tert-butyl-protected Leu-enkephalins have been synthesized as models to demonstrate the utility of the linker.

    PMID:
    18722403
    [PubMed - indexed for MEDLINE]

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