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Lipase‐catalyzed synthesis of structured triacylglycerides from 1,3‐diacylglycerides
Author(s) -
Wongsakul Sirirung,
HKittikun Aran,
Bornscheuer Uwe T.
Publication year - 2004
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-004-0873-z
Subject(s) - lipase , oleic acid , lauric acid , caprylic acid , chemistry , glycerol , yield (engineering) , catalysis , solvent , fatty acid , organic chemistry , oleyl alcohol , enzyme , biochemistry , materials science , metallurgy
A new method for the lipase‐catalyzed synthesis of structured TAG (ST) is described. First, sn 1,3‐dilaurin or‐dicaprylin were enzymatically synthesized using different published methods. Next, these were esterified at the sn 2‐position with oleic acid or its vinyl ester using different lipases. Key to successful enzymatic synthesis of ST was the choice of a lipase with appropriate FA specificity, i.e., one that does not act on the FA already present in the sn 1,3‐DAG, but that at the same time exhibits high selectivity and activity toward the FA to be introduced. Reactions were performed in the presence of organic solvents or in solvent‐free systems under reduced pressure. With this strategy, mixed ST containing the desired compounds 1,3‐dicaprylol‐2‐oleyl‐glycerol or 1,3‐dilauroyl‐2‐oleyl‐glycerol (CyOCy or LaOLa) were obtained at 87 and 78 mol% yield, respectively, using immobilized lipases from Burkholderia cepacia (Amano PS‐D) in n ‐hexane at 60°C. However, regiospecific analysis with porcine pancreatic lipase indicated that in CyOCy, 25.7% caprylic acid and in LaOLa 11.1% lauric acid were located at the sn 2‐position. Oleic acid vinyl ester was a better acyl donor than oleic acid. Esterification of sn 1,3‐DAG and free oleic acid gave very low yield (<20%) of ST in a solvent system and moderate yield (>50%) in a solvent‐free system under reduced pressure.