Nitrilase-producing acidovorax facilis

Details Nitrilase-producing acidovorax facilis Nitrilase-producing acidovorax facilis

1997-12-10

2000-05-23

Lankford, Jr., Leon B.

Chemistry: molecular biology and microbiology

Micro-organism, per se ; compositions thereof; proces of...

Bacteria or actinomycetales; media therefor

4352533, 435227, 435128, C12N 112, C12N 978

Patent

active

060664908

ABSTRACT:
A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha.,.omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrilecarboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and amidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.

REFERENCES:
Bargar et al., Rapid and Efficient Method for Dehydration of Primary Amides to Nitriles, Chemical Abstracts, 94, No. 3, Abstract No. 14593, Jan. 19, 1981.
M. Cushman et al., A Synthesis of 2-alkyl and 2-benzyl Substituted Acrylonitriles from 2-alkyl and 2-benzylidenecyanoacetate Esters under Mild Conditions, Chemical Abstract, 113, No. 25, Abstracts No. 230773.
J. Lange et al., Direct Pyradazine Ring Synthesis from Beta-cyano Esters, Chemical Abstracts, 119, No. 21, Abstract No. 225898, Nov. 22, 1993.

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