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Highly selective synthesis of 1,3-oleoyl-2-palmitoylglycerol by lipase catalysis.
Biotechnology and Bioengineering ( IF 3.5 ) Pub Date : 1999-07-23
U Schmid 1 , U T Bornscheuer , M M Soumanou , G P McNeill , R D Schmid
Affiliation  

1,3-Oleoyl-2-palmitoylglycerol (OPO), an important structured triglyceride in infant nutrition, was synthesized by a two-step process in high yields and purity using sn1,3-regiospecific lipases. In the first step, tripalmitin (TP) was subjected to an alcoholysis reaction in an organic solvent catalyzed by sn1,3-regiospecific lipases yielding the corresponding 2-monopalmitin (2-MP). The 2-MP was isolated in up to 85% yield and >95% purity by crystallization and esterified in the second step with oleic acid using the same lipases to form the structured triglyceride OPO in up to 78% yield containing 96% palmitic acid in the sn2-position. Water activity, solvent, as well as carrier for lipase immobilization strongly influenced the yield and purity of products in both steps. The best results were achieved with lipases from Rhizomucor miehei and Rhizopus delemar immobilized on EP 100 and equilibrated to a water activity of 0.43. Special emphasis was given to develop this process in solvents that are allowed to be used in foodstuffs and to perform the second step in a solvent-free system.

中文翻译:

通过脂肪酶催化高选择性合成1,3-油酰基-2-棕榈酰基甘油。

1,3-Oleoyl-2-palmitoylglycerol(OPO),婴儿营养中重要的结构化甘油三酸酯,使用sn1,3-regiospecific脂肪酶通过两步过程以高产率和高纯度合成。在第一步中,将三棕榈精蛋白(TP)在有机溶剂中进行醇解反应,该溶剂由sn1,3-区域特异性脂肪酶催化,生成相应的2-单棕榈精蛋白(2-MP)。通过结晶分离2-MP,收率高达85%,纯度> 95%,并在第二步中使用相同的脂肪酶与油酸酯化,形成结构化的甘油三酸酯OPO,收率高达78%,其中含有96%的棕榈酸。 sn2位置。在两个步骤中,水活度,溶剂以及用于脂肪酶固定化的载体都强烈影响产物的产率和纯度。用固定在EP 100上并平衡至水活度为0.43的来自根瘤菌(Rhizomucor miehei)和深根霉(Rhizopus delemar)的脂肪酶获得了最佳结果。特别强调了在允许用于食品的溶剂中开发该方法,并在无溶剂系统中执行第二步。
更新日期:2019-11-01
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