A novel method for the synthesis of symmetrical triacylglycerols by enzymatic transesterification. (November 2015)

• Record Type: Journal Article
• Authors: Tang, Wenjia; Wang, Xiaosan; Huang, Jianhua; Jin, Qingzhe; Wang, Xingguo
• Is Part Of: Bioresource technology. Volume 196(2015)
• Page Start: 559
• Page End: 565
• Publication Date: 2015-11
• Subjects: Microbial oil -- Symmetrical triacylglycerols -- Fatty acid vinyl ester -- Polyunsaturated fatty acids -- Irreversible transesterification; Biomass -- Periodicals; Biomass energy -- Periodicals; Bioremediation -- Periodicals; Agricultural wastes -- Periodicals; Factory and trade waste -- Periodicals; Organic wastes -- Periodicals; Bioénergie -- Périodiques; Déchets agricoles -- Périodiques; Déchets industriels -- Périodiques; Déchets organiques -- Périodiques; Déchets (Combustible) -- Périodiques; 662.88
• DOI: 10.1016/j.biortech.2015.08.024
• Languages: English
• ISSNs: 0960-8524

Abstract

Highlights: Symmetrical triacylglycerols (STAGs) had been synthesized by transesterification. Enzymatic transesterification for STAGs synthesis is a greener route. Enzymatic reaction using fatty acid vinyl ester as acyl donor is irreversible. Low acyl migration rate during transesterification were due to the irreversibility. 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.