Kinetic resolution of primary 2-methyl-substituted alcohols via Pseudomonas cepacia lipase-catalysed enantioselective acylation

2000 ◽  
pp. 367-376 ◽  
Author(s):  
Ove Nordin ◽  
Ba-Vu Nguyen ◽  
Carin Vörde ◽  
Erik Hedenström ◽  
Hans-Erik Högberg
Keyword(s):  
Kinetic Resolution ◽  
Pseudomonas Cepacia ◽  
Enantioselective Acylation ◽  
Pseudomonas Cepacia Lipase

scholarly journals Lipase-Catalyzed Kinetic Resolution of Alcohols as Intermediates for the Synthesis of Heart Rate Reducing Agent Ivabradine

Catalysts ◽  
2021 ◽  
Vol 11 (1) ◽  
pp. 53
Author(s):  
Anna Morandini ◽  
Arianna Rossetti ◽  
Alessandro Sacchetti
Keyword(s):  
Kinetic Resolution ◽  
Enzymatic Reaction ◽  
Chronic Stable Angina ◽  
Pseudomonas Cepacia ◽  
Chiral Hplc ◽  
Reaction Conditions ◽  
Chiral Amine ◽  
Enantiomeric Ratio ◽  
Pseudomonas Cepacia Lipase ◽  
Synthetic Sequence

Ivabradine (Corlanor®), is a chiral benzocycloalkane currently employed and commercialized for the treatment of chronic stable angina pectoris and for the reduction in sinus tachycardia. The eutomer (S)-ivabradine is usually produced via chiral resolution of intermediates, by employing enantiopure auxiliary molecules or through preparative chiral HPLC separations. Recently, more sustainable biocatalytic approaches have been reported in literature for the preparation of the chiral amine precursor. In this work, we report on a novel biocatalyzed pathway, via a resolution study of a key alcohol intermediate used as a precursor of the chiral amine. After screening several enzymatic reaction conditions, employing different lipases and esterases both for the esterification and hydrolysis reactions, the best result was achieved with Pseudomonas cepacia Lipase and the final product was obtained in up to 96:4 enantiomeric ratio (e.r.) of an ivabradine alcohol precursor. This enantiomer was then efficiently converted into the desired amine in a facile three step synthetic sequence.

Immobilization of Pseudomonas cepacia lipase on layered double hydroxide of Zn/Al-Cl for kinetic resolution of rac-1-phenylethanol

2019 ◽  
Vol 130 ◽  
pp. 109365 ◽  
Author(s):  
Glauco Silva Dias ◽  
Pamela Taisline Bandeira ◽  
Silvia Jaerger ◽  
Leandro Piovan ◽  
David Alexander Mitchell ◽  
...  
Keyword(s):  
Layered Double Hydroxide ◽  
Kinetic Resolution ◽  
Pseudomonas Cepacia ◽  
Pseudomonas Cepacia Lipase ◽  
Double Hydroxide

Kinetic resolution of 4-chloro-2-(1-hydroxyalkyl)pyridines using Pseudomonas cepacia lipase

2006 ◽  
Vol 1 (4) ◽  
pp. 2061-2067 ◽  
Author(s):  
Eduardo Busto ◽  
Vicente Gotor-Fernández ◽  
Vicente Gotor
Keyword(s):  
Kinetic Resolution ◽  
Pseudomonas Cepacia ◽  
Pseudomonas Cepacia Lipase

scholarly journals Kinetic Resolution of Optically Pure 3-Alkanol by Pseudomonas cepacia Lipase-Catalyzed Transesterification with Vinyl Acetate in Organic Solvent

2003 ◽  
Vol 52 (7) ◽  
pp. 375-386 ◽  
Author(s):  
Hirofumi HIRATA ◽  
Masako IKUSHIMA ◽  
Michitoshi WATANABE ◽  
Keiyo KAWAUCHI ◽  
Masato MIYAGISHI ◽  
...  
Keyword(s):  
Organic Solvent ◽  
Vinyl Acetate ◽  
Kinetic Resolution ◽  
Pseudomonas Cepacia ◽  
Pseudomonas Cepacia Lipase ◽  
Optically Pure
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