Application of L-threonine aldolase-catalyzed reaction to the preparation of protected 3R,5R-dihydroxy-L-homoproline as a mimetic of idulonic acid

Authors

  • Tsuyoshi Miura,

    1. Frontier Research Program, The Institute of Physical and Chemical Research, Saitama, Japan
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  • Tetsuya Kajimoto

    Corresponding author
    1. Frontier Research Program, The Institute of Physical and Chemical Research, Saitama, Japan
    2. Department of Biotechnology, Tokyo University of Agriculture and Technology, Tokyo, Japan
    • Department of Biotechnology, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan
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Abstract

A facile synthesis of 3R,5R-dihydroxy-L-homoproline as idulonic acid mimic, of which the carboxyl and 3-hydroxyl groups were protected, was attained using L-threonine aldolase-catalyzed reaction. Idulonic acid is a key acidic sugar of the b-FGF binding domain in heparin and heparan sulfate. Moreover, the synthetic precursor of N-acetyl-4-deoxy-D-mannosamine, which is a potent inhibitor of NeuAc synthase, was prepared from the side product of the enzymatic aldol condensation. Chirality 13:577–580, 2001. © 2001 Wiley-Liss, Inc.

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