Regioselective biocatalytic hydrolysis of ( E, Z)-2-methyl-2-butenenitrile for production of ( E)-2-methyl-2-butenoic acid

Acidovorax facilis 72W nitrilase catalyzed the regioselective hydrolysis of ( E, Z)-2-methyl-2-butenenitrile, producing only ( E)-2-methyl-2-butenoic acid with no detectable conversion of ( Z)-2-methyl-2-butenenitrile. ( E)-2-Methyl-2-butenoic acid, produced in aqueous solution as the ammonium salt,...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2004-01, Vol.60 (3), p.577-581
Main Authors: Hann, Eugenia C, Sigmund, Amy E, Fager, Susan K, Cooling, Frederick B, Gavagan, John E, Bramucci, Michael G, Chauhan, Sarita, Payne, Mark S, DiCosimo, Robert
Format: Article
Language:English
Subjects:
Amidase
Angelic acid
Enzyme catalysis
Nitrilase
Nitrile hydratase
Tiglic acid
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Acidovorax facilis 72W nitrilase catalyzed the regioselective hydrolysis of ( E, Z)-2-methyl-2-butenenitrile, producing only ( E)-2-methyl-2-butenoic acid with no detectable conversion of ( Z)-2-methyl-2-butenenitrile. ( E)-2-Methyl-2-butenoic acid, produced in aqueous solution as the ammonium salt, was readily separated from ( Z)-2-methyl-2-butenenitrile, and isolated in high yield and purity. The combination of nitrile hydratase and amidase activities of several Comamonas testosteroni strains were also highly regioselective for the production of ( E)-2-methyl-2-butenoic acid from ( E, Z)-2-methyl-2-butenenitrile. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2003.10.120