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.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► 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.