ENZYME-CATALYZED TRANSESTERIFICATION OF AMINOPHOSPHONIC ACIDS .2. ISOTHREONINE-P ANALOGS

In this work, we used lipases to resolve kinetically the four possible configurations of an important aminophosphonic acid: isothreonine-P ( isoTHR-P). We synthesized a diastereomeric mixture of N-Cbz-isoTHR-P(O )(OEt)(2) and also each diastereomer of isoTHR-P(O)(OEt)(2). Several e nzymatic reactions were then performed (hydrolysis and transesterifica tion) with these compounds. The lipases used (mainly Pseudomonas fluor escens and Candida rugosa) proved to be diastereoselective and chimios elective, but no enantioselectivity was observed.