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Kinetic resolution of propranolol by a lipase-catalyzed N-acetylation

✍ Scribed by Tzyy-Wen Chiou; Cheng-Chi Chang; Chung-Torr Lai; Dar-Fu Tai

Publisher
Elsevier Science
Year
1997
Tongue
English
Weight
216 KB
Volume
7
Category
Article
ISSN
0960-894X

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✦ Synopsis

An enzymatic method for the direct resolution of propranolol is described.

Candida cylindracea lipase enantioselectively catalyzed N-acetylation of S-propranolol with isopropenyl acetate in isopropyl ether. The ee values of the two enantiomers of N-acetylpropranolol were determined by an HPLC equipped with a chiral column. The effects of organic solvent nature and substrate concentration on enantioselectivity were also studied.

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The lipase-catalyzed acetylation of a broad spectrum of configurations of the 2-hydroxy acids 1 were assigned by comparison of the gas-chromatographic data with that of racemic 2-hydroxy acids 1 to their 2-acetoxy acids 2 was shown to proceed with high enantioselectivity. Thus, the literature-known