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Enzymatic esterification of glycerol I. Lipase‐catalyzed synthesis of regioisomerically pure 1,3‐ sn ‐diacylglycerols
Author(s) -
Berger Matthias,
Laumen Kurt,
Schneider Manfred P.
Publication year - 1992
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/bf02541057
Subject(s) - rhizomucor miehei , lipase , glycerol , chemistry , organic chemistry , catalysis , diethyl ether , rhizopus oryzae , solvent , triacylglycerol lipase , fatty acid , enzyme , fermentation
Regioisomerically pure 1,3‐ sn ‐diacylglycerols are conveniently prepared in high yields (>80%) and in large quantities by enzymatic esterification of glycerol in the presence of various 1,3‐selective lipases (Chromobacterium viscosum, Rhizopus delemar, Rhizomucor miehei) and a variety of different acyl donors like free fatty acids, fatty acid alkyl esters and vinyl esters. All reactions are carried out in aprotic organic solvents of low water content, namely n ‐hexane, diethyl ether or tBuOMe. The creation of an artificial interphase between the solvent‐immiscible hydrophilic glycerol and the hydrophobic reaction media by the adsorption of glycerol onto a solid support prior to use was essential for the success of these transformations. The effects of reaction conditions and the regioselectivities of the lipases on the product yields are described in detail.