Efficient Transformation of Castor Oil Using a Highly-Densed Phase Boundary Enzyme

2014 Fiscal Year Final Research Report

• Project/Area Number: 25620079
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Mie University
• Principal Investigator: SHIMIZU Makoto 三重大学, 工学(系)研究科(研究院), 教授 (30162712)
• Project Period (FY): 2013-04-01 – 2015-03-31
• Keywords: ひまし油 / 不斉加水分解 / 1,3-ジアシルグリセロール / 固定化リパーゼ / 1-モノアシルグリセロール / グリコシル化反応 / SQDG / フロー合成

Outline of Final Research Achievements

We examined asymmetric hydrolysis of 1,3-diacyl glycerol or its derivatives with lipases. Use of Lipase PS immobilized on ceramic was not effective to give only a low yield of the product. When 2-BOM- or 2-MOM-1,3-diacyl glycerols were used, Lipase PS worked very well to give the monoacylated glycerol in >90% de. Transformations into SQDG was next examined. Glycasilation of the diacylated glycerol with the imidate derived from sulfenylated glucose in the presence of TMSOTf gave a precursor to SQDG in good yield. Further transformations involving oxidation of the sulfur moiety and the removal of the protecting groups as well as application to a flow synthesis are under way.

Free Research Field

有機合成化学