Enzyme-catalysed hydrolyses of some meso-diesters

Abstract

The diester 7 is hydrolysed, using porcine pancreatic lipase as catalyst, to give the monoester 8. The latter compound has been converted into the known azido alcohol 9 and into the purine derivative 10. Pig liver esterase (ple) catalysed hydrolysis of the diester 11 gave the acid 13 not the enantiomer 12 as previously reported. The structure of 13 was determined by its conversion into the compound ent-10. The diesters 17 and 18 are converted into the mono-esters 20 and 21 respectively using pie: hydrolysis of the diester 16 yields a mono-acid of high optical purity. The structure of this mono-acid is believed to be that shown in formula 19.