147963-52-8

Upstream product

• 100-39-0 benzyl bromide 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 13880-89-2 3-hydroxyglutaronitrile 
• 138145-57-0 3-O-(benzyl)-glutaronitrile 

Relevant academic research and scientific papers

Nitrile hydratase enzymes in organic synthesis: Enantioselective synthesis of the lactone moiety of the mevinic acids

(R)-4-Hydroxy-5-cyanopentene (-)-9, a known precursor of the protected lactone moiety of the mevinic acids 1, has been prepared in 9 steps from (S)-3-(benzyloxy)-4-cyanobutanoic acid 5 (88% e.e.) which was obtained by the asymmetric 2 step hydrolysis of 3-benzyloxyglutaronitrile 4 involving the successive activity of a nitrile hydratase and an amidase enzyme.

Stereoselective Hydrolysis of Nitriles and Amides Under Mild Conditions Using a Whole Cell Catalyst

An immobilised whole cell Rhodococcus sp. (SP 361) has been shown to be an effective catalyst for the stereoselective hydrolysis of both racemic and prochiral nitrile containing compounds. 2-Alkyl-arylacetonitriles 6a-8a were hydrolysed to (S)-acids and (R)-amides whereas the closely related substrate 9a gave the (R)-acid.A series of prochiral dinitriles 10a-13a were hydrolysed to the corresponding (S)-acids with e.e.'s 22-84percent.Models to account for the stereoselectivity of the enzymic hydrolyses have been proposed.

Enzymic Hydrolysis of Prochiral Dinitriles

A series of prochiral 3-hydroxyglutaronitrile derivatives 1-5 has been enzymically hydrolysed to the corresponding nitrile-carboxylic acids 1b-5b with enantiomeric excesses ranging from 22-84percent.In all cases the products were of the (S)-configuration.

Microbial Hydrolysis of 3-Substituted Glutaronitriles

Rhodococcus butanica ATCC 21197 preferentially hydrolyzed pro-S cyano group of 3-substituted glutaronitriles with an aromatic ring.A product with high e.e. (>99 percent) was obtained from 3-benzoyloxy derivative.