Prepn. of optically active alcohol(s) and carbonic acid di:ester(s) - by hydrolysis of racemic carbonic acid di:ester(s) with lipase

摘要

Optically active alcohols and optically active diesters of carbonic acid are prepd. by reacting racemates of carbonic acid diesters with lipases at 20-60 deg.C. Pref. the carbonic acid diester has the formula R1-O-C(O)-O-R2, where R1 = a non-chiral alkyl gp.; R2 has at least 1 optically active centre, and may be (substd.) (cyclo)alkyl or heterocycloalkyl. Hydrolysis is with pancreatic lipase (pref.) or lipases from Pseudomonas sp., at pH 5-7.7, without addn. of base, or with addn. of bases to form a carbonic acid / bicarbonate buffer system. USE/ADVANTAGE - The optically active alcohols and esters are useful intermediates. The system is self-buffering and control of pH is not needed. The enantio-selectivity is good. Optically active alcohols and esters which are unobtainable, difficult to obtain, by known processes, can be made. The CO2 formed acts as protective gas and reduces the risk of microbial contamination and premature breakdown of the enzyme by foreign proteases.