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Chemoenzymatic synthesis of rasagiline mesylate using lipases

Paper ID Volume ID Publish Year Pages File Format Full-Text
39216 45813 2015 7 PDF Available
Title
Chemoenzymatic synthesis of rasagiline mesylate using lipases
Abstract

•A straightforward chemoenzymatic synthesis of rasagiline mesylate has been developed.•The key steps involved kinetic lipase-mediated resolution and Mitsunobu reaction.•T. lanuginosus was robust biocatalyst afforded S-indanol with e.e. > 99% in 15 min.•Immobilized T. lanuginosus could be effectively reused in ten reaction cycles.

A straightforward chemoenzymatic synthesis of rasagiline mesylate has been developed. The key steps for the introduction of chirality involved kinetic enzymatic resolution with lipases via acetylation of rac-indanol and an inversion configuration Mitsunobu reaction of the produced (S)-indanol. Immobilized lipase from Thermomyces lanuginosus proved to be a robust biocatalyst in the kinetic resolution, leading to (S)-indanol with high selectivity (e.e. > 99%, E > 200) in just 15 min, at 35 °C, in hexane, being reused for ten-times without significant loss of the activity and selectivity.

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Keywords
Rasagiline mesylate; Chemoenzymatic synthesis; Kinetic enzymatic resolution; Lipases; Mitsunobu reaction; Indanol; Pseudomonas fluorescens; Amano AK; Thermomyces lanuginosus
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 492, 25 February 2015, Pages 76–82
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Price was $35.95
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