One-pot enzymatic synthesis of docosahexaenoic acid-rich triacylglycerols at the sn-1(3) position using by-product from selective hydrolysis of tuna oil.
Docosahexaenoic acid (DHA)-rich oil has been industrially produced by selective hydrolysis of tuna oil with a lipase that acts weakly on DHA. The free fatty acids (FFAs) generated in this process as by-products contain a high DHA concentration (46wt%) but are treated as industrial waste. This study attempted to reuse these by-product FFAs using a one-pot process, and succeeded in producing triacylglycerols (TAGs) through the esterification of the by-product FFAs with glycerol using immobilized Rhizomucor miehei lipase. Regiospecific analysis of the resulting TAGs showed that the content of DHA at the sn-1(3) position (51.7mol%) was higher than the content of DHA at the sn-2 position (17.3mol%). The DHA distribution in TAGs synthesized in this study was similar to the DHA distribution in TAGs from seal oil.
Nagao
Toshihiro
T
Biomaterials and Commodity Chemicals Research Division, Osaka Municipal Technical Research Institute, Osaka 536-8553, Japan. nagao@omtri.or.jp
Watanabe
Yomi
Y
Maruyama
Kazuaki
K
Momokawa
Yuusuke
Y
Kishimoto
Noriaki
N
Shimada
Yuji
Y
D000818:Animals; D002175:Candida / Q000201:enzymology; D002625:Chemistry, Organic / Q000379:methods*; D004281:Docosahexaenoic Acids / Q000737:chemistry / Q000378:metabolism*; D004800:Enzymes, Immobilized / Q000378:metabolism; D004951:Esterification; D005395:Fish Oils / Q000378:metabolism*; D005990:Glycerol / Q000378:metabolism; D006868:Hydrolysis; D008049:Lipase / Q000378:metabolism*; D020103:Rhizomucor / Q000201:enzymology; D013237:Stereoisomerism; D013696:Temperature; D013997:Time Factors; D014280:Triglycerides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D014413:Tuna / Q000378:metabolism*
D004800:Enzymes, Immobilized; D005395:Fish Oils; D014280:Triglycerides; D004281:Docosahexaenoic Acids; D008049:Lipase; D005990:Glycerol