Abstract
Microorganims of the bovine rumen fluid biocatalyzed the reduction of nitro-compound substrates to yield the respective amines. This enzymatic process, using ruminal contents, has rarely been reported in associa- tion with the bioreduction of nitro groups. The biotransformation reactions catalyzed by this system were de- pendent of both the electronic characteristics and the area/volume of the nitro-substrates confirming the processes are enzymatic. The semi-preparative scale biotransformation went by in good yield showing the rumen fluid may be employed in the synthesis of amines under very mild conditions and, moreover, it may have application in the bioremediation of nitro-compounds.
Highlights
Much work has been done to find effective ways of bioremediating of serious environmental nitro-substituted contaminants, i.e. the explosives TNT, HMX, and RDX [1-5]
Biotransformations of the nitro-compounds 1-8 (Scheme 1) were carried out using bovine rumen fluid obtained from dairy cows
The processes were conducted either on a small scale (1 mg of substrate solubilised in methanol in 1 mL of ruminal fluid and 4 mL of McDougall’s buffer, which is similar to the bicarbonate buffer from the salivary glands of the ruminant [23]) or on a semipreparative scale (500 mL of ruminal fluid/McDougall’s buffer, 30 mg of nitro-compound 2 solubilised in methanol) and the mixtures were incubated without agitation for 24 hours, in the small scale, or 5 days, in semi-preparative scale, at 39 ̊C
Summary
Much work has been done to find effective ways of bioremediating of serious environmental nitro-substituted contaminants, i.e. the explosives TNT, HMX, and RDX [1-5]. Many chemicals and pharmaceuticals are or require an amine intermediates and only relatively small number of chemical routes have involve safety, scalability and environmental acceptability for large-scale manufacturing [8-10]. In this sense, several biocatalytic processes have been described [7,11,12]. The ruminants have three additional compartments (rumen, reticulum and omasum) before the true stomach (abomasum) These compartments allow the microbial population to extract and the host to absorb energy from fibrous plant material not otherwise available to mammalian enzymes. Examples of xenobiotic transformations by rumen microbes have been reported for toxicants in forages such as pyrrolizine alkaloids, fumonisin, alflatoxin [15-18], and nitropropionic acid, and TNT that were converted to the corresponding amine and hydroxylamine derivatives [4,19]
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