Development of a hypusine reagent for peptide synthesis

    Authors

    R. J. Bergeron; C. Ludin; R. Muller; R. E. Smith;O. Phanstiel

    Comments

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    Abbreviated Journal Title

    J. Org. Chem.

    Keywords

    ESTERS CAM-ESTERS; PROTEIN-SYNTHESIS; INITIATION; DEPROTECTION; TRANSLATION; DERIVATIVES; ACIDS; ANION; Chemistry, Organic

    Abstract

    The synthesis of a reagent that enables the incorporation of the unusual amino acid (2S,9R)hypusine (Hpu) into peptide sequences is described. The reagent, (2S,SR)-11-[(benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2- [(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)- 7-azaundecanoic acid, is utilized in the synthesis of a hexapeptide containing the primary pentapeptide sequence of the eukaryotic initiation factor eIF-5A, L-Cys-L-Thr-Gly-Hpu-L-His-Gly. The reagent is shown to be effective for both solution phase and Merrifield resin synthesis.

    Journal Title

    Journal of Organic Chemistry

    Volume

    62

    Issue/Number

    10

    Publication Date

    1-1-1997

    Document Type

    Article

    Language

    English

    First Page

    3285

    Last Page

    3290

    WOS Identifier

    WOS:A1997XG22100060

    ISSN

    0022-3263

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