title: A novel method for the synthesis of symmetrical triacylglycerols by enzymatic transesterification.
abstract: A novel two-step enzymatic method is described in this study to synthesize symmetrical triacylglycerols (TAGs) with arachidonic acid (ARA) at the sn-2 position. The processes included the synthesis of 2-monoacylglycerols (2-MAGs) rich in 2-arachidonoylglycerol (2-AG) by enzymatic ethanolysis and the synthesis of symmetrical TAGs by enzymatic transesterification between 2-MAGs and vinyl palmitate. Under the optimal conditions, desired symmetrical TAGs were obtained at 89% yield. In this study, vinyl palmitate rather than palmitic acid was used as a novel acyl donor to react with 2-MAGs. It was the first study reporting the synthesis of symmetrical TAGs by enzymatic transesterification. The reaction using fatty acid vinyl ester as acyl donor is irreversible and temperature is low. Low-temperature reaction greatly suppressed the acyl migration of 2-MAGs and the irreversible reaction is much more effective compared to reversible reactions using free fatty acid and fatty acid ester as acyl donors.
authors: State Key Laboratory of Food Science and Technology, Synergetic Innovation Center of Food Safety and Nutrition, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu 214122, PR China.
authors: Wenjia
authors: W
authors: Tang
authors: State Key Laboratory of Food Science and Technology, Synergetic Innovation Center of Food Safety and Nutrition, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu 214122, PR China. Electronic address: wxstongxue@163.com.
authors: Xiaosan
authors: X
authors: Wang
authors: State Key Laboratory of Food Science and Technology, Synergetic Innovation Center of Food Safety and Nutrition, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu 214122, PR China.
authors: Jianhua
authors: J
authors: Huang
authors: State Key Laboratory of Food Science and Technology, Synergetic Innovation Center of Food Safety and Nutrition, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu 214122, PR China.
authors: Qingzhe
authors: Q
authors: Jin
authors: State Key Laboratory of Food Science and Technology, Synergetic Innovation Center of Food Safety and Nutrition, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu 214122, PR China.
authors: Xingguo
authors: X
authors: Wang
mesh_terms: D016718:Arachidonic Acid; D001709:Biotechnology / Q000379:methods*; D004798:Enzymes; D004951:Esterification; D014280:Triglycerides / Q000737:chemistry / Q000378:metabolism
chemical_list: D004798:Enzymes; D014280:Triglycerides; D016718:Arachidonic Acid
keywords: Fatty acid vinyl ester; Irreversible transesterification; Microbial oil; Polyunsaturated fatty acids; Symmetrical triacylglycerols