Chemical Synthesis of Biologically Active Monoglycosylated GM2-Activator Protein Analogue Using N-Sulfanylethylanilide Peptide

Authors

  • Kohei Sato,

    1. Institute of Health Bioscience and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505 (Japan)
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  • Prof. Dr. Akira Shigenaga,

    1. Institute of Health Bioscience and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505 (Japan)
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  • Keisuke Kitakaze,

    1. Institute of Health Bioscience and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505 (Japan)
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  • Ken Sakamoto,

    1. Institute of Health Bioscience and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505 (Japan)
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  • Prof. Dr. Daisuke Tsuji,

    1. Institute of Health Bioscience and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505 (Japan)
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  • Prof. Dr. Kohji Itoh,

    1. Institute of Health Bioscience and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505 (Japan)
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  • Prof. Dr. Akira Otaka

    Corresponding author
    1. Institute of Health Bioscience and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505 (Japan)
    • Institute of Health Bioscience and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505 (Japan)
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  • This research was supported in part by a Grant-in-Aid for Scientific Research (KAKENHI) and research grants from the Takeda Science and the Uehara Memorial Foundations. K.S. is grateful for a scholarship from the Yoshida Scholarship Foundation.

Abstract

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Going to SEA(lide): Total chemical synthesis of a 162-residue glycoprotein analogue of the monoglycosylated human GM2-activator protein (GM2AP) was achieved. Key steps were the use of N-sulfanylethylanilide (SEAlide) peptides in the kinetic chemical ligation synthesis of a large peptide fragment, and a convergent native chemical ligation for final fragment assembly.

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