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Keywords:

  • enzymatic aldol condensation;
  • 3R,5R-dihydroxy- L-homoproline;
  • idulonic acid;
  • iminocyclitol;
  • β-hydroxy-α-L-amino acid;
  • heparin;
  • heparan sulfate

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.