(656e) Asymmetric Bioreduction of Aromatic Nitro Compounds and Nitroalkenes with Enoate Reductase and Nitroreductase Enzymes

Yanto, Y., Georgia Institute of Technology
Hall, M., Georgia Institute of Technology
Bommarius, A. S., Georgia Institute of Technology

The use of biocatalysts for the synthesis of enantio pure compounds attracts increasing attention in fine chemistry and pharmaceutical industry. Biore-duction of activated alkenes by enoate reductases is one of the emerging biosynthetic tools for substrates such as enals, enones, and nitroalkenes [1]. Nitroreductase activity on aromatic compounds is also often observed [2]. In this study, we have characterized several enzymes for their reduction poten-tial on various nitro-substituted compounds. High degrees of conversion, along with high regio- and stereo-selectivity were obtained in the reduction of substrates such as 1-nitro-2-phenylpropene. In order to broaden the appli-cability of these enzymes, we investigated the substrate specificity using wide range of C=C activating groups including aldehyde-, ketone-, imide-, and carboxylic acid- moieties. The study explored the possibilities of reduc-tion amination of nitro-substituted alkenes for efficient synthesis of amines.

[1] Toogood HS, Fryszkowska A, Adv Synthesis & Catalysis. 2008, 17, 350

[2] Roldan M, Perez-Reinado E, Fems Microbiology Review. 2008, 3, 32