Porcine pancreatic lipase mediated regio- and stereoselective hydrolysis: chemoenzymatic synthesis of (2S,3S)-2-amino-3,4-dihydroxybutyric acid

Porcine pancreatic lipase was used in the chemoenzymatic hydrolysis of 2-az ido-3-hydroxy-3-methylcarbonyloxybutyl acetate The reaction occurred with h igh regio- and stereoselectivity to give enantiomerically pure (2S.3R)-3-az ido-2-4-dihydroxy butyl acetate 5 (e.e. > 99%) which was easily converted t o (2S,3S)-2-amno-3.4-dihydroxybutyric acid 1. an important synthetic interm ediate in the synthesis of beta -lactam antibiotics and phytosiderophores, (C) 2001 Elsevier Science Ltd. All rights reserved.