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

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 u sing 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 pot ent inhibitor of NeuAc synthase, was prepared from the side product of the enzymatic aldol condensation. Chirality 13:577-580, 2001. (C) 2001 Wiley-Li ss, Inc.