title: 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.
authors.affiliation: State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi, 214122, Jiangsu, People's Republic of China, wxstongxue@163.com.
authors.forename: Xiaosan
authors.initials: X
authors.lastname: Wang
authors.forename: Wanzhen
authors.initials: W
authors.lastname: Zou
authors.forename: Xuemei
authors.initials: X
authors.lastname: Sun
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.forename: Liying
authors.initials: L
authors.lastname: Wei
authors.forename: Qingzhe
authors.initials: Q
authors.lastname: Jin
authors.forename: Xingguo
authors.initials: X
authors.lastname: Wang
mesh_terms: D004075:Diglycerides / Q000378:metabolism; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D005990:Glycerol / Q000378:metabolism; D008049:Lipase / Q000378:metabolism*; D019301:Oleic Acid / Q000378:metabolism; D019308:Palmitic Acid / Q000378:metabolism; D013696:Temperature; D013997:Time Factors; D014280:Triglycerides / Q000138:chemical synthesis* / Q000378:metabolism*; D014753:Vinyl Compounds / Q000378:metabolism
chemical_list: D004075:Diglycerides; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D014280:Triglycerides; D014753:Vinyl Compounds; D019301:Oleic Acid; D019308:Palmitic Acid; C093667:Novozyme 435; D008049:Lipase; C089743:1,3-diolein; C011566:vinyl acetate; D005990:Glycerol; C095376:1,3-dioleoyl-2-palmitoylglycerol