Enzymatic nitration of the oleic acid derivatives: Synthesis,isolation and characterization |
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Affiliation: | 1. Key Laboratory of Marine Chemistry Theory and Technology (Ocean University of China), Ministry of Education, 238 Songling Road, Qingdao 266100, China;2. College of Chemistry & Chemical Engineering, Ocean University of China, 238 Songling Road, Qingdao 266100, China |
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Abstract: | Unsaturated fatty acids are nitrated endogenously to produce nitrated lipids. Recent studies have shown that these nitrated lipids have high chemical reactivity and profound biological implications. We report an efficient, enzymatic synthesis of nitrated derivatives of the oleic acid. The methyl oleate could react with NO and horseradish peroxidase (HRP)/H2O2/NO based nitrating systems to give various nitration products which could be isolated by silica gel column and TLC fractionation, respectively. As reacting directly with NO, the obtained products contain (E)-methyl 9-nitrooctadec-9-enoate (1), (E)-methyl 10-nitrooctadec-9-enoate (2), (E)-methyl 9-nitrooctadec-10-enoate (3) and (E)-methyl 10-nitrooctadec-8-enoate (4), characterized by extensive IR, NMR and GC–MS analysis. Whereas the products of the reaction between the methyl oleate and NO with the presence of HRP/H2O2 were mainly composed of (E)-methyl 9-nitrooctadec-9-enoate and (E)-methyl 10-nitrooctadec-9-enoate. The improving selectivity of the products is attributed to the HRP catalysis system. |
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Keywords: | Methyl oleate Unsaturated fatty acid Enzymatic nitration Horseradish peroxidase |
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