Chemoenzymatic synthesis of 1,3-dioleoyl-2-palmitoylglycerol

Abstract

We report the synthesis of 1,3-dioleoyl-2-palmitoylglycerol (OPO) by a three-step method. Vinyl oleate was first synthesized by transvinylation between vinyl acetate and oleic acid. This was further reacted with glycerol at 35 °C for 8 h using 10% (w/v) Novozym 435 to synthesize 1,3-diolein. The 1,3-diolein content in the crude reaction mixture was 90.8% and was obtained at 82.3% (w/w) yield with 98.6% purity after purification. Finally, OPO was chemically synthesized by reacting purified 1,3-diolein with palmitic acid. 94.8% OPO was produced in the crude reaction mixture and the regiopurity of OPO after purification was 98.7% at 90.5% yield based on positional distribution analysis. This is an innovative approach for the synthesis of 1,3-diolein in a solvent-free system as an alternative to previously presented studies that applied solvent system.

Differences in Absorption and Metabolism between Structured 1,3-Oleate-2-palmitate Glycerol and 1-Oleate-2-palmitate-3-linoleate Glycerol on C57BL/6J Mice

“…This approach is a transesterification of glycerol using OA vinyl esters and immobilized Novozym 435. In this method, the lipase displays perfect regioselectivity by acting exclusively at the primary alcoholic positions of the glycerol, thereby producing the desired 1,3-diolein without any trace of 1,2-diolein. , Subsequently, PA was introduced into the midposition of the 1,3-diolein using EDCI and DMAP to produce the OPO oil (Figure A). The major advantage of using EDCI and DMAP is the dramatic difference in R f values on TLC between the TAG products and the chemical catalysts.…”

Emulsifying Properties of an Homologous Series of Medium- and Long-Chain d-Maltotriose Esters and their Impacts on the Viabilities of Selected Cell Lines

“…Maltotriose (>80.0%) was purchased from the Bidepharm Co. Ltd. (Shanghai, China), while vinyl decanoate (>99.0%), vinyl laurate (>99.0%), vinyl myristate (>99.0%), vinyl palmitate (>96.0%), and vinyl stearate (>95.0%) were all supplied by the Tokyo Chemical Industry Co. Ltd. (Tokyo, Japan). Vinyl oleate was prepared using a reported transesterification method …”

Facile Preparation of Dopamine-Modified Magnetic Zinc Ferrite Immobilized Lipase for Highly Efficient Synthesis of OPO Functional Lipid

“…Next, according to the method of methyl esterification in fatty acid composition analysis and the parameters of GC, 2-MAGs were methyl esterified and analyzed by GC. The proportion of PA-Sn2 of the total content PA is an essential indicator for judging the synthesized OPO [28], which was calculated using formula (3):…”