Insight into the stereoselectivity of PPL-catalyzed formation of polyesters from phenyl glycidyl ether and succinic anhydride

Analysis of the stereoselectivity that would be expected in the Pig Pancreatic Lipase-catalyzed oligomerization of succinic anhydride and phenyl glycidyl ether is carried out.The results show that no stereoselection was recorded at any step of the suggested mechanism of the process: opening of the chiral epoxide into 1,2-diol, nucleophilic attack of the chiral acylenzyme by a chiral diol, or by the hydroxyl group of a growing oligomer.

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► Pig Pancreatic Lipase-catalyzed oligomerisation.
► Enzyme catalyzed polymerization from succinic acid and phenylglycidyl ether.
► Stereoselectivity in PPL-catalyzed formation of oligomers.
► Stereoselectivity in the process, since chiral, racemic epoxides were used.