151715-97-8Relevant articles and documents
Organic co-solvents restore the inherently high enantiomeric ratio of lipase B from Candida antarctica in hydrolytic resolution by relieving the enantiospecific inhibition of product alcohol
Lundhaug, Kamilla,Overbeeke, P.L. Antoine,Jongejan, Jaap A.,Anthonsen, Thorleif
, p. 2851 - 2856 (2007/10/03)
The enantiomeric ratio in the hydrolysis of racemic 3-chloro-1- phenylmethoxy-2-propyl butanoate with lipase B from Candida antarctica, CALB, is raised from E=50 to E=180 upon addition of acetone to the aqueous medium. This co-solvent effect is now explained as an enantiospecific inhibition of the lipase by the liberated alcohol. In the range from 0 to 30% acetone, the effect correlates with the increased solubility of the alcohol in the reaction medium. Free and immobilized CALB show similar behaviour.
Enzymatic resolution of butanoic esters of 1-phenylmethyl and 1-[2-phenylethyl]ethers of 3-chloro-1,2-propanediol
Partali,Waagen,Alvik,Anthonsen
, p. 961 - 968 (2007/10/02)
The enzymatic hydrolysis of butanoic esters of 1-phenylmethyl- and 1-[2-phenylethyl] ethers of 3-chloro-1,2-propanediol has been studied by using lipases. Highest enantiomeric ratio was obtained with PPL for the phenylmethyl ether and with Amano SAM II for the phenylethyl ether. The absolute configurations of the products was verified in two ways. Both the produced alcohols and the remaining esters were converted into the corresponding glycidyl ethers which also were synthesised in homochiral forms starting from (S)-epichlorohydrin. The produced alcohols and the remaining esters were prepared independently from (S)-epichlorohydrin.
