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Efficient and Stereoselective Synthesis of α(2→9) Oligosialic Acids: From Monomers to Dodecamers

Authors

  • Dr. Kuo-Ching Chu,

    1. Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
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  • Dr. Chien-Tai Ren,

    1. Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
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  • Dr. Chun-Ping Lu,

    1. Institute of Biological Chemistry, Academia Sinica (Taiwan)
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  • Che-Hsiung Hsu,

    1. Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
    2. Chemical Biology and Molecular Biophysics, Taiwan International Graduate Program, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
    3. Institute of Bioinformatics and Structural Biology, National Tsing-Hua University, Hsin-Chu (Taiwan)
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  • Dr. Tsung-Hsien Sun,

    1. Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
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  • Dr. Jeng-Liang Han,

    1. Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
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  • Dr. Bikash Pal,

    1. Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
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  • Tsung-An Chao,

    1. Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
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  • Yung-Feng Lin,

    1. Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
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  • Prof. Shih-Hsiung Wu,

    1. Institute of Biological Chemistry, Academia Sinica (Taiwan)
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  • Prof. Chi-Huey Wong,

    Corresponding author
    1. Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
    2. Chemical Biology and Molecular Biophysics, Taiwan International Graduate Program, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
    • Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
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  • Prof. Chung-Yi Wu

    Corresponding author
    1. Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
    2. Chemical Biology and Molecular Biophysics, Taiwan International Graduate Program, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
    • Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115 (Taiwan)
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  • This work was supported by the Academia Sinica and National Science Council, Taiwan (Grant no NSC 99-2113-M-001-008-MY2 to C.Y.W.)

Abstract

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The chain gang: The α(2→9) dodecasialic acid has been stereoselectively synthesized in 12 steps by using a convergent block synthesis (see scheme). The use of chloroacetyl protecting groups and a phosphate group as a leaving group led to the improvement of the α selectivity of the glycosylation reactions, thus allowing synthesis of oligomers.

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