Chemoenzymic Production of Lactams from Aliphatic α,ω-Dinitriles

Five- and six-membered ring lactams have been prepared by first converting an aliphatic α,ω-dinitrile to an ω-cyanocarboxylic acid ammonium salt, using a microbial cell catalyst having an aliphatic nitrilase activity (Acidovorax facilis 72W, ATCC 55746) or a combination of nitrile hydratase and amid...

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Bibliographic Details
Published in:Journal of organic chemistry 1998-07, Vol.63 (14), p.4792-4801
Main Authors: Gavagan, John E, Fager, Susan K, Fallon, Robert D, Folsom, Patrick W, Herkes, Frank E, Eisenberg, Amy, Hann, Eugenia C, DiCosimo, Robert
Format: Article
Language:English
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Summary:Five- and six-membered ring lactams have been prepared by first converting an aliphatic α,ω-dinitrile to an ω-cyanocarboxylic acid ammonium salt, using a microbial cell catalyst having an aliphatic nitrilase activity (Acidovorax facilis 72W, ATCC 55746) or a combination of nitrile hydratase and amidase activities (Comamonas testosteroni 5-MGAM-4D, ATCC 55744). The ω-cyanocarboxylic acid ammonium salt was then directly converted to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate ω-cyanocarboxylic acid or ω-aminocarboxylic acid. Only one of two possible lactam products was produced from α-alkyl-substituted α,ω-dinitriles, where the nitrilase of A. facilis 72W regioselectively hydrolyzed only the ω-cyano group to produce a single cyanocarboxylic acid ammonium salt in greater than 98% yield.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9804386