fulltext.study @t Gmail

Chemoenzymatic synthesis of gabapentin by combining nitrilase-mediated hydrolysis with hydrogenation over Raney-nickel

Paper ID Volume ID Publish Year Pages File Format Full-Text
49726 46763 2015 5 PDF Available
Title
Chemoenzymatic synthesis of gabapentin by combining nitrilase-mediated hydrolysis with hydrogenation over Raney-nickel
Abstract

•An efficient chemoenzymatic route for the production of gabapentin was developed.•1-Cyanocyclohexaneacetic acid was synthesized by a greatly improved nitrilase.•A feasible procedure for producing the regioselective nitrilase was demonstrated.•Direct hydrogenation of 1-cyanocyclohexaneacetic acid was performed successfully.

An efficient chemoenzymatic process is devised for synthesizing high-purity gabapentin. 1-Cyanocyclohexaneacetic acid was first produced in 0.94 M from 1.0 M 1-cyanocycloalkaneacetonitrile by a greatly improved nitrilase from Acidovorax facilis ZJB09122, resulting in a commercially attractive bioprocess with an outstanding space-time yield of 461 g/L/day. The resulting aqueous 1-cyanocycloalkaneacetic acid was then directly converted to 2-azaspiro [4.5] decan-3-one without further purification in subsequent hydrogenation by Raney-nickel, followed by simple chemical steps to afford gabapentin in high purity and 77.3% overall yield from 1-cyanocyclohexylacetonitrile. The simplicity of the process makes this new pathway suitable for large-scale preparation.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Biocatalysis; Gabapentin; Hydrogenation; Protein engineering; Regioselectivity
First Page Preview
Chemoenzymatic synthesis of gabapentin by combining nitrilase-mediated hydrolysis with hydrogenation over Raney-nickel
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us
Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 66, 5 June 2015, Pages 121–125
Authors
, , , , , , , ,
Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us