Biocatalytic Oxidation of 2-Methylquinoxaline to 2-Quinoxalinecarboxylic Acid

A microbial process using the fungus Absidia repens ATCC 14849 is described for the oxidation of 2-methylquinoxaline to 2-quinoxalinecarboxylic acid. A campaign consisting of three 14000-L runs produced 20.5 kg of the acid with a 28% overall yield. The bioconversion gave a lower yield compared with...

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Bibliographic Details
Published in:Organic process research & development 2002-07, Vol.6 (4), p.477-481
Main Authors: Wong, John W, Watson, Harry A, Bouressa, James F, Burns, Michael P, Cawley, James J, Doro, Albert E, Guzek, Donald B, Hintz, Michael A, McCormick, Ellen L, Scully, Douglas A, Siderewicz, Joseph M, Taylor, William J, Truesdell, Susan J, Wax, Richard G
Format: Article
Language:English
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Summary:A microbial process using the fungus Absidia repens ATCC 14849 is described for the oxidation of 2-methylquinoxaline to 2-quinoxalinecarboxylic acid. A campaign consisting of three 14000-L runs produced 20.5 kg of the acid with a 28% overall yield. The bioconversion gave a lower yield compared with a three step chemical synthesis (35%), but was carried out in one pot, and avoided safety issues with a di-N-oxide intermediate. Although successfully scaled to produce kilograms of 2-quinoxalinecarboxylic acid for synthesis of a drug candidate, the A. repens bioconversion is unsuitable for further scale-up due to low product concentration (∼1 g/L). A second microbial process using Pseudomonas putida ATCC 33015 is also described for the oxidation of 2-methylquinoxaline. The P. putida bioconversion gave an 86% in situ yield at 8-L scale and yielded a product concentration approximately 10-fold greater than that of the A. repens bioconversion.
ISSN:1083-6160
1520-586X
DOI:10.1021/op025501e