Application of L‐threonine aldolase‐catalyzed reaction to the preparation of protected 3R,5R‐dihydroxy‐L‐homoproline as a mimetic of idulonic acid
- 1 January 2001
- Vol. 13 (9) , 577-580
- https://doi.org/10.1002/chir.1180
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.Keywords
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