JPS6253155B2 - - Google Patents
Info
- Publication number
- JPS6253155B2 JPS6253155B2 JP60171021A JP17102185A JPS6253155B2 JP S6253155 B2 JPS6253155 B2 JP S6253155B2 JP 60171021 A JP60171021 A JP 60171021A JP 17102185 A JP17102185 A JP 17102185A JP S6253155 B2 JPS6253155 B2 JP S6253155B2
- Authority
- JP
- Japan
- Prior art keywords
- lipase
- reaction
- hydrolysis
- type
- acetone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 102000004882 Lipase Human genes 0.000 claims description 18
- 108090001060 Lipase Proteins 0.000 claims description 18
- 239000004367 Lipase Substances 0.000 claims description 18
- 235000019421 lipase Nutrition 0.000 claims description 18
- 150000002327 glycerophospholipids Chemical class 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000015439 Phospholipases Human genes 0.000 description 4
- 108010064785 Phospholipases Proteins 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000008777 Glycerylphosphorylcholine Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- SUHOQUVVVLNYQR-MRVPVSSYSA-O glycerylphosphorylcholine Chemical compound C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO SUHOQUVVVLNYQR-MRVPVSSYSA-O 0.000 description 3
- 229960004956 glycerylphosphorylcholine Drugs 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000004443 Ricinus communis Nutrition 0.000 description 2
- 241000179532 [Candida] cylindracea Species 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- FRMZOWIQVCBEAC-UHFFFAOYSA-N glycerylphosphorylethanolamine Chemical compound OCCN(P(O)(O)=O)CC(O)CO FRMZOWIQVCBEAC-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 238000006257 total synthesis reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 102000011720 Lysophospholipase Human genes 0.000 description 1
- 108020002496 Lysophospholipase Proteins 0.000 description 1
- 235000002233 Penicillium roqueforti Nutrition 0.000 description 1
- 229920001872 Spider silk Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- LNPVLXNEAYADKT-UHFFFAOYSA-N benzyl 3-amino-2-hydroxypropanoate Chemical compound NCC(O)C(=O)OCC1=CC=CC=C1 LNPVLXNEAYADKT-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
【発明の詳細な説明】
(a) 産業上の利用分野
本発明は、１位、２位OH型のグリセロリン脂
質の製造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (a) Field of Industrial Application The present invention relates to a method for producing a glycerophospholipid having 1- and 2-OH type glycerophospholipids.
(b) 従来の技術
従来、１位、２位いずれもフリーのOH型であ
るグリセロリン脂質を製造するには、全合成する
方法もしくはジアシルグリセロリン脂質を加水分
解試薬で化学的に分解する方法が用いられてき
た。全合成の方法としては、例えばイソプロピル
デングリセロールをフエニルホスフオリルクロラ
イドでリン酸化し、これにエチレンクロロヒドリ
ンを加え、還元、加水分解、トリメチルアミン処
理を行うとグリセリルホスホリルコリンが得られ
る（E.Baer、D.Buchnea、A.G.Newconbe：J.
Am.Chem.Soc.、78、232（1956））。また上記リ
ン酸化物にカルボベンゾキシエタノールアミンを
加え、還元、加水分解することによりグリセリル
ホスホリルエタノールアミンが得られる（E.
Baer、H.C.Staneer：J.Am.Chem.Soc.、75、
4510（1953））。(b) Conventional technology Conventionally, in order to produce glycerophospholipids in which both the 1st and 2nd positions are free OH type, a method of total synthesis or a method of chemically decomposing diacylglycerophospholipids with a hydrolysis reagent has been used. I've been exposed to it. As a total synthesis method, for example, isopropyldene glycerol is phosphorylated with phenylphosphoryl chloride, ethylene chlorohydrin is added to this, and glycerylphosphorylcholine is obtained by reduction, hydrolysis, and trimethylamine treatment (E. Baer, D. Buchnea, AG Newcombe: J.
Am.Chem.Soc., 78 , 232 (1956)). In addition, glycerylphosphorylethanolamine can be obtained by adding carbobenzoxyethanolamine to the above phosphorus oxide, reducing and hydrolyzing it (E.
Baer, H.C.Staneer: J.Am.Chem.Soc., 75 ,
4510 (1953)).
一方加水分解する方法としては、例えばレシチ
ンにテトチブチルアンモニウムヒドロキシドを作
用させることによつて、アシル基を２つとも脱離
させることができる（H.Brocherhoff、M.
Yurkowski：Can.J.Biochem.、43、177
（1965））。 On the other hand, as a method for hydrolysis, for example, by treating lecithin with tetrabutylammonium hydroxide, both acyl groups can be eliminated (H. Brocherhoff, M.
Yurkowski: Can.J.Biochem., 43 , 177
(1965)).
(c) 発明が解決しようとする問題点
従来の合成法は、多段階を経る反応であり、ま
た使用する試薬も高価で危険なものが多い。さら
には副生成物も多く、精製に多大な労力を必要と
し、収率も低い。加水分解試薬を用いる方法は反
応自体は簡便であるが、副反応が生じやすく収率
や純度が悪いという欠点を有している。(c) Problems to be Solved by the Invention Conventional synthesis methods involve reactions that involve multiple steps, and the reagents used are often expensive and dangerous. Furthermore, there are many by-products, a great deal of effort is required for purification, and the yield is low. Although the reaction itself is simple in the method using a hydrolysis reagent, it has the disadvantage that side reactions are likely to occur and yield and purity are poor.
一方リン脂質のアシル基を酵素によつて加水分
解すること自体は従来から知られており、ホスホ
リパーゼA1は１位のアシル基を加水分解し、ホ
スホリパーゼA2は２位のアシル基を加水分解す
る。またホスホリパーゼＢはホスホリパーゼＡで
得られたリゾレシチンを加水分解する。しかし、
いずれのホスホリパーゼも特殊で高価なものであ
り、さらにはこれらを混合し、１段階で加水分解
するには、至適PH、温度の違い、阻害物質の問題
等があり、今まで実用化されていなかつた。 On the other hand, it has long been known that the acyl groups of phospholipids are hydrolyzed by enzymes; phospholipase A 1 hydrolyzes the 1-position acyl group, and phospholipase A 2 hydrolyzes the 2-position acyl group. do. Phospholipase B also hydrolyzes lysolecithin obtained with phospholipase A. but,
All phospholipases are special and expensive, and furthermore, in order to mix them and hydrolyze them in one step, there are problems such as differences in optimal pH, temperature, and inhibitors, so they have not been put into practical use until now. Nakatsuta.
本発明の目的は従つて、前記した化学的手段や
酵素を用いる方法にみられる諸欠点が払拭され
た、１位、２位、OH型のグリセロリン脂質を製
造する方法を提供することにある。 Therefore, an object of the present invention is to provide a method for producing 1-position, 2-position, and OH type glycerophospholipids, which eliminates the various drawbacks found in the methods using chemical means and enzymes described above.
(d) 問題点を解決するための手段
本発明者らは、かかる目的を達成すべく、鋭意
研究の結果、リパーゼを用いると数種の酵素を混
合することなく、１段階でグリセロリン脂質の１
位および２位のアシル基を非選択的に加水分解で
きることを見出した。(d) Means for Solving the Problems In order to achieve the above object, the present inventors have conducted extensive research and have found that by using lipase, one step of glycerophospholipid can be achieved without mixing several types of enzymes.
It has been found that the acyl groups at position and 2 can be hydrolyzed non-selectively.
本発明は、このような知見に基づいて完成され
たもので、ジアシルグリセロリン脂質の２個所の
アシル基を同時にリパーゼにより加水分解するこ
とを特徴とする１位、２位OH型のグリセロリン
脂質の製造法である。 The present invention was completed based on such findings, and is a method for producing glycerophospholipids with OH type at the 1- and 2-positions, which is characterized by simultaneously hydrolyzing two acyl groups of diacylglycerophospholipids using lipase. It is the law.
以下、本発明つき詳しく説明する。 The present invention will be explained in detail below.
本発明に用いるリン脂質は、ホスフアチジルコ
リン、ホスフアチジルエタノールアミン、ホスフ
アチジルイノシトール、ホスフアチジルセリン、
ホスフアチジン酸等のジアシルグリセロリン脂質
の１種あるいは２種以上の混合物である。また純
度は、本発明の反応には大きく影響しないので問
題とはならないが、目的物は純度の良いものが要
求されることが多いので反応後もしくは反応前に
精製することが望ましい。 The phospholipids used in the present invention include phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine,
It is one type or a mixture of two or more types of diacylglycerophospholipids such as phosphatidic acid. Further, purity is not a problem as it does not greatly affect the reaction of the present invention, but since the target product is often required to be of high purity, it is desirable to purify it after or before the reaction.
使用するリパーゼは、アオカビ、コウジカビ、
クモノスガビ由来のリパーゼにおいてもわずかに
反応は進むが、トリグリセリドの加水分解におい
て位置特異性が少なくランダム加水分解を行う酵
母、ヒマシ由来のリパーゼが好ましい。特に酵母
由来のリパーゼは、グリセロリン脂質の１位、２
位の加水分解速度の差が少なく本発明を実施する
に最も適している。 The lipases used are Blue mold, Aspergillus mold,
Although the reaction progresses slightly with lipase derived from Arachnidium chinensis, lipase derived from yeast and castor is preferred because it has less positional specificity and performs random hydrolysis in the hydrolysis of triglycerides. In particular, yeast-derived lipase is the 1st and 2nd glycerophospholipid.
There is little difference in hydrolysis rate, making it the most suitable for carrying out the present invention.
反応は、通常の加水分解と同様で水溶液中で酵
素反応を行えばよい。緩衝液や活性化剤を加える
方が反応は効率的に進むが、特に使用する必要は
ない。またリパーゼを固定化して使用してもよ
い。固定化法は、通常の担体結合法、架橋法、包
括法いずれも可能である。固定化法を用いれば、
カラム充填による連続反応や膜に固定化し反応の
促進と精製を容易にできることは従来の酵素によ
る加水分解と同様であり、本発明の反応になんら
影響を及ぼさない。 The reaction is similar to normal hydrolysis, and the enzymatic reaction may be carried out in an aqueous solution. The reaction will proceed more efficiently if a buffer or activator is added, but there is no need to add a buffer or activator. Alternatively, lipase may be immobilized and used. As the immobilization method, any of the usual carrier binding methods, crosslinking methods, and entrapping methods can be used. If you use the immobilization method,
Continuous reaction by column packing and facilitation of reaction promotion and purification by immobilization on a membrane are similar to conventional hydrolysis using enzymes, and do not affect the reaction of the present invention in any way.
上記の加水分解反応によつて得られた水溶液か
ら脂肪酸を除去することにより、目的とする１
位、２位OH型のグリセロリン脂質が得られる。 By removing fatty acids from the aqueous solution obtained by the above hydrolysis reaction, the target 1
Glycerophospholipids with the OH type at the 2nd and 2nd positions are obtained.
脂肪酸を除去する方法としては、溶剤分別、膜
分離、吸着等の操作が可能である。溶剤分別法と
しては、アセトン分別が最も容易で効率も良い。
水溶液に直接多量のアセトンを添加しても良い
が、好ましくは水溶液を乾燥後、乾燥物の２〜20
倍量のアセトンで１〜２回よく洗浄する。濾別し
たケーキが、粘性を帯びている場合は、さらにア
セトンで洗浄し、白〜淡褐色の粉末を得る。真空
乾燥を行えば、１位、２位OH型のグリセロリン
脂質が得られる。 As a method for removing fatty acids, operations such as solvent fractionation, membrane separation, and adsorption are possible. As a solvent fractionation method, acetone fractionation is the easiest and most efficient.
A large amount of acetone may be added directly to the aqueous solution, but preferably after drying the aqueous solution,
Wash thoroughly once or twice with twice the amount of acetone. If the filtered cake is viscous, it is further washed with acetone to obtain a white to light brown powder. If vacuum drying is performed, glycerophospholipids with the 1- and 2-position OH type can be obtained.
(e) 実施例
実施例 １
高純度大豆．ホスフアチジルコリンPC−95
（日清製油製 ジアシルホスフアチジルコリン含
量：95％）10ｇを水100ｇに添加し、ホモミキサ
ーで均質化する。この水溶液に酵母
（Candidacylindracea）リパーゼ0.1ｇを添加す
る。35℃、10時間撹拌反応後、水溶液を減圧乾燥
する。得られた乾燥物約10ｇにアセトン100mlを
加え、固型物を細かくしながらよく撹拌する。濾
別し、ケーキを再度アセトン100mlで分別する。
得られたケーキを減圧乾燥後、ヘキサン100mlに
溶解し、不溶物となるリパーゼを除去する。再度
減圧乾燥し、グリセリルホスホリルコリン３ｇ
（純度90％：TCL分析）が得られる。(e) Examples Example 1 High purity soybeans. Phosphatidylcholine PC-95
Add 10 g of diacylphosphatidylcholine content: 95% (manufactured by Nisshin Oil Co., Ltd.) to 100 g of water and homogenize with a homomixer. 0.1 g of yeast (Candidacylindracea) lipase is added to this aqueous solution. After stirring the reaction at 35°C for 10 hours, the aqueous solution is dried under reduced pressure. Add 100 ml of acetone to about 10 g of the dried product obtained, and stir well while breaking up the solids. Filter and separate the cake again with 100 ml of acetone.
After drying the obtained cake under reduced pressure, it is dissolved in 100 ml of hexane to remove insoluble lipase. Dry under reduced pressure again and add 3g of glycerylphosphorylcholine.
(purity 90%: TCL analysis) is obtained.
実施例 ２
ジアシルホスフアチジルエタノールアミン（純
度60％）10ｇを水100ｇに添加し、ホモミキサー
で均質化する。この水溶液に酵母
（Candidacylindracea）リパーゼ0.1ｇを添加す
る。35℃、10時間撹拌反応後、水溶液を減圧乾燥
する。得られた乾燥物を約10ｇにアセトン100ml
を加え、固型物を細かくしながらよく撹拌する。
濾別してケーキを再度アセトン100mlで分別す
る。得られたケーキを減圧乾燥後、ヘキサン100
mlに溶解し、不溶物となるリパーゼを除去する。
再度減圧乾燥し、グリセリルホスホリルエタノー
ルアミン3.5ｇ（純度50％：TLC分析）が得られ
る。Example 2 10 g of diacylphosphatidylethanolamine (purity 60%) is added to 100 g of water and homogenized using a homomixer. 0.1 g of yeast (Candidacylindracea) lipase is added to this aqueous solution. After stirring the reaction at 35°C for 10 hours, the aqueous solution is dried under reduced pressure. Add 100ml of acetone to about 10g of the dried product.
Add and stir well while breaking up the solids.
Filter and separate the cake again with 100 ml of acetone. After drying the obtained cake under reduced pressure, add 100% hexane.
ml and remove insoluble lipase.
Dry under reduced pressure again to obtain 3.5 g of glycerylphosphorylethanolamine (purity 50%: TLC analysis).
実施例 ３
実施例１と同様にジアシルホスフアチジルコリ
ンにヒマシリパーゼを作用する。25℃、20時間作
用させ、実施例１と同様に精製すると純度40％の
グリセリルホスホリルコリンが得られる。Example 3 In the same manner as in Example 1, diacylphosphatidylcholine is treated with castor lipase. After reacting at 25°C for 20 hours and purifying in the same manner as in Example 1, glycerylphosphorylcholine with a purity of 40% is obtained.
(f) 発明の効果
本発明によれば、従来数段階の複雑な工程で製
造されていた１位、２位OH型のグリセロリン脂
質を、リパーゼを用い、１段階で製造することが
でき、製造法が簡便化される。１種類のリパーゼ
による反応なので、反応、精製が容易であり、か
つ低温でエステル結合にのみ作用する反応の為、
副反応が生じにくい。さらには、特殊な試薬を用
いない為、安全性も高い。(f) Effects of the invention According to the present invention, glycerophospholipids with the 1- and 2-position OH types, which were conventionally produced in a complicated process of several steps, can be produced in one step using lipase. The law will be simplified. Because the reaction uses one type of lipase, it is easy to react and purify, and because the reaction only acts on ester bonds at low temperatures,
Side reactions are less likely to occur. Furthermore, since no special reagents are used, it is highly safe.
こうして得らた１位、２位OH型のグリセロリ
ン脂質は、OH基に脂肪酸、アルコール、糖、リ
ン酸等の置換基を導入するための中間体とし有益
である他、水溶性リン脂質として医薬、化粧品、
食品等の工業用原材料として使用可能である。 The glycerophospholipid with OH type at the 1- and 2-positions thus obtained is useful as an intermediate for introducing substituents such as fatty acids, alcohols, sugars, and phosphoric acid into the OH group, and is also used as a water-soluble phospholipid for pharmaceutical use. ,cosmetics,
It can be used as an industrial raw material for foods, etc.
Claims (1)
基を同時にリパーゼにより加水分解することを特
徴とする１位、２位OH型のグリセロリン脂質の
製法。 ２ リパーゼとして、トリグリセリドに対してラ
ンダム加水分解をするリパーゼを使用する特許請
求の範囲第１項記載の製法。 ３ 酵母由来のリパーゼを用いる特許請求の範囲
第２項記載の製法。[Scope of Claims] 1. A method for producing a glycerophospholipid of the 1- and 2-position OH type, which comprises simultaneously hydrolyzing two acyl groups of the diacylglycerophospholipid using lipase. 2. The manufacturing method according to claim 1, wherein a lipase that randomly hydrolyzes triglyceride is used as the lipase. 3. The production method according to claim 2, which uses yeast-derived lipase.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17102185A JPS6232890A (en) | 1985-08-05 | 1985-08-05 | Production of glycerophospholipid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17102185A JPS6232890A (en) | 1985-08-05 | 1985-08-05 | Production of glycerophospholipid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6232890A JPS6232890A (en) | 1987-02-12 |
| JPS6253155B2 true JPS6253155B2 (en) | 1987-11-09 |
Family
ID=15915617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17102185A Granted JPS6232890A (en) | 1985-08-05 | 1985-08-05 | Production of glycerophospholipid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6232890A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6411737U (en) * | 1987-07-14 | 1989-01-23 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5747484A (en) * | 1976-08-19 | 1982-03-18 | Eastman Kodak Co | Hydrolysis of plasma phospholipid |
-
1985
- 1985-08-05 JP JP17102185A patent/JPS6232890A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5747484A (en) * | 1976-08-19 | 1982-03-18 | Eastman Kodak Co | Hydrolysis of plasma phospholipid |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6411737U (en) * | 1987-07-14 | 1989-01-23 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6232890A (en) | 1987-02-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20040235119A1 (en) | Method for the production of phospholipids | |
| JP4045100B2 (en) | Method for producing lysophosphatidylethanolamine | |
| JP2794574B2 (en) | Method for producing lysolecithin | |
| WO1998003529A1 (en) | Process for the preparation of sphingolipids and sphingolipid derivatives | |
| US7189544B2 (en) | Enzymatic modification of lecithin | |
| CN104818303A (en) | Method for enzymatic preparation of glycerophosphorylcholine | |
| JPS6253155B2 (en) | ||
| US5100787A (en) | Method for preparing highly purified phosphatidylinositol | |
| KR102433277B1 (en) | Choline alfoscerate composition manufacturing method using fatty oil | |
| JP2011211921A (en) | Method for producing cyclic phosphatidic acid | |
| JPH0279990A (en) | Production of phosphatidylserine | |
| JPS63123389A (en) | Production of phospholipid-d-serine derivative by enzymatic method | |
| JP2006197842A (en) | Composition having phospholipase a1 activity, 2-acyl type lysophospholipid obtained by using the same and method for producing those | |
| JP2009148244A (en) | Method for producing lysophosphatidylethanolamine | |
| JP2707642B2 (en) | Method for producing lysophospholipid | |
| JP2830072B2 (en) | Enzymatic degradation method of synthetic phosphatidylcholine | |
| KR100225669B1 (en) | Process for preparing highly pure phospholipid using enzyme | |
| JPH09296197A (en) | Dehydration and purification of oil and fat | |
| JPH03123493A (en) | Hydrolysis of diacylglyceroline lipid | |
| AU2003286065B2 (en) | Isolation of inositol from plant materials | |
| JPH0761273B2 (en) | Phospholipid modification method | |
| JP4467722B2 (en) | Method for producing high-purity lysophosphatidylinositol and glycolipid | |
| JP2683590B2 (en) | Method for producing enzyme-converted phospholipid | |
| CA2506509C (en) | Purification of inositol from plant materials | |
| JPH0471497A (en) | Preparation of monoacylglycerophospholipid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| LAPS | Cancellation because of no payment of annual fees |