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Enzymatic esterification of glycerol III. Lipase‐catalyzed synthesis of regioisomerically pure 1,3‐ sn ‐diacylglycerols and 1 (3)‐ rac ‐monoacylglycerols derived from unsaturated fatty acids
Author(s) -
Waldinger Claudia,
Schneider Manfred
Publication year - 1996
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/bf02523518
Subject(s) - lipase , glycerol , erucic acid , chemistry , catalysis , substrate (aquarium) , yield (engineering) , oleic acid , organic chemistry , fatty acid , linoleic acid , enzyme , triacylglycerol lipase , biochemistry , materials science , metallurgy , oceanography , geology
Lipases that display high regioselectivities and broad substrate tolerance were used as catalysts for the efficient esterification of glycerol under the conditions of irreversible acyl transfer. A variety of unsaturated fatty acids, such as oleic, linoleic, erucic, ricinolic, hydroxystearic and coriolic acid, were used for this purpose in the form of their vinyl esters. Suitable biocatalysts were chosen on the basis of systematic screening experiments regarding their regioselectivities (RE) and substrate tolerances. Distinct differences were found and expressed in numerical RE values as a measure for differences of these biocatalysts as being specific, selective, and nonspecific. Based on these experiments, a variety of molecules were synthesized on a preparative scale (>150 mmol) in good yield (ca.85%) and with high regioisomerical purities (>95% RE).