NDLI: Lipase-catalyzed synthesis of chiral triglycerides

Content Provider	Springer Nature Link
Author	Chandler, Ian C. Quinlan, Paul T. McNeill, Gerald P.
Copyright Year	1998
Abstract	Under certain reaction conditions, the acidolysis of tripalmitin with oleic acid using immobilized lipase from Rhizomucor miehei resulted in a higher level of monosubstituted oleoyldipalmitoyl (OPP) triglycerides than had been predicted according to kinetic modeling. The reaction products were subjected to chiral analysis by high-performance liquid chromatography (HPLC), which indicated that the enzyme was more active at the sn-1 position of the triglyceride than at the sn-3 position, resulting in synthesis of the chiral triglyceride 1-oleoyl-2,3-dipalmitoyl-sn-glycerol. A kinetic model was developed and was correlated with the HPLC method to provide a simple means to predict the stereoselectivity of lipase-catalyzed reactions. By using the model, the stereoselectivity of immobilized Rhizomucor miehei lipase was found to depend strongly on the initial water activity (a $_{w}$) of the reaction mixture, with greater selectivity occurring at lower a $_{w}$. The sn-1 selectivity was essentially maintained using various solvents, or without solvent, when a $_{w}$ was kept constantly low. Variation in the fatty acid composition of the triglyceride indicated that shorter-chain fatty acids result in greater stereoselectivity, while variation of the chainlength of the free fatty acid indicated an enhancement by the longest chainlength. The stereoselectivity of this lipase was confirmed using a new $^{13}$C nuclear magnetic resonance method. By using immobilized R. miehei lipase at low a $_{w}$ approximately 80% of the chiral triglyceride found in the reaction mixture was the sn-1 enantiomer, at high reaction conversion.
Starting Page	1513
Ending Page	1518
Page Count	6
File Format	PDF
ISSN	0003021X
Journal	Journal of the American Oil Chemists' Society
Volume Number	75
Issue Number	11
e-ISSN	15589331
Language	English
Publisher	Springer-Verlag
Publisher Date	1998-01-01
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Acidolysis chain length chiral free fatty acid lipase solvent type source organism stereoselectivity triglyceride water activity Industrial Chemistry/Chemical Engineering Analytical Chemistry Chemistry/Food Science Biotechnology Biomaterials Agriculture
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Chemical Engineering

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