JPH0220289A - Production of farnesylacetic acid geranyl ester - Google Patents
Production of farnesylacetic acid geranyl esterInfo
- Publication number
- JPH0220289A JPH0220289A JP16882188A JP16882188A JPH0220289A JP H0220289 A JPH0220289 A JP H0220289A JP 16882188 A JP16882188 A JP 16882188A JP 16882188 A JP16882188 A JP 16882188A JP H0220289 A JPH0220289 A JP H0220289A
- Authority
- JP
- Japan
- Prior art keywords
- lipase
- geraniol
- modified
- farnesylacetic acid
- reaction
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- -1 farnesylacetic acid geranyl ester Chemical class 0.000 title abstract description 11
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims abstract description 24
- 102000004882 Lipase Human genes 0.000 claims abstract description 22
- 108090001060 Lipase Proteins 0.000 claims abstract description 22
- 239000004367 Lipase Substances 0.000 claims abstract description 19
- 235000019421 lipase Nutrition 0.000 claims abstract description 19
- 239000005792 Geraniol Substances 0.000 claims abstract description 12
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims abstract description 12
- 229940113087 geraniol Drugs 0.000 claims abstract description 12
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- ZGIGZINMAOQWLX-UHFFFAOYSA-N Farnesyl acetate Natural products CC(C)=CCCC(C)=CCCC(C)=CCOC(C)=O ZGIGZINMAOQWLX-UHFFFAOYSA-N 0.000 claims description 13
- 229940007703 farnesyl acetate Drugs 0.000 claims description 13
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- ZGIGZINMAOQWLX-NCZFFCEISA-N 3,7,11-Trimethyl-2,6,10-dodecatrienyl acetate Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\COC(C)=O ZGIGZINMAOQWLX-NCZFFCEISA-N 0.000 claims description 6
- ZPACYDRSPFRDHO-ROBAGEODSA-N Gefarnate Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(=O)OC\C=C(/C)CCC=C(C)C ZPACYDRSPFRDHO-ROBAGEODSA-N 0.000 claims description 4
- 229960003779 gefarnate Drugs 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- VOKDWPMRYSKGTB-NCZFFCEISA-N (4e,8e)-5,9,13-trimethyltetradeca-4,8,12-trienoic acid Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(O)=O VOKDWPMRYSKGTB-NCZFFCEISA-N 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 125000003277 amino group Chemical group 0.000 abstract description 2
- 238000010898 silica gel chromatography Methods 0.000 abstract description 2
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 241000589516 Pseudomonas Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- WJHFZYAELPOJIV-IJFRVEDASA-N (2E,6E)-farnesoic acid Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\C(O)=O WJHFZYAELPOJIV-IJFRVEDASA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 241000589538 Pseudomonas fragi Species 0.000 description 1
- 241000179532 [Candida] cylindracea Species 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000010701 ester synthesis reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、抗潰瘍治療薬として使用されているファルネ
シル酢酸ゲラニルエステルの製造法に関し、詳しくは０
−メトキシポリエチレングリコールで修飾されたリパー
ゼの存在下において、１．１．１− ）ジクロロエタン
中でゲラニオールにファルネシル酢酸を反応させること
によりなるファルネシル酢酸ゲラニルエステルの製造法
に関するものである。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a method for producing farnesyl acetate geranyl ester, which is used as an anti-ulcer therapeutic agent.
The present invention relates to a method for producing geranyl farnesyl acetate by reacting geraniol with farnesyl acetate in 1.1.1-) dichloroethane in the presence of a lipase modified with -methoxypolyethylene glycol.
ファルネシル酢酸ゲラニルエステルの公知製造法として
は、ゲラニオールとファルネシル酢酸とを硫酸等の触媒
存在下で共沸によって水を除去しながら還流する方法（
特許公告、昭３９−５６１９号、ベルギー特許第６１７
９９４号）があるが、この方法ではエステル化の収率が
低く且エステル化触媒のため目的物の異性化を生じる欠
点がある。このような欠点を改良する方法として、先ず
ゲラニオールと硼酸を反応させ活性エステルとした後、
ファルネシル酢酸と反応させてファルネシル酢酸ゲラニ
ルエステルを製造する方法（特許公告、昭４８３１０８
８号）あるいはファルネシル酢酸とゲラニオ−、、をカ
７．．オ）、Ｊ、ア豐、ネオ、７ケ１．アセタール存在
下で反応させる方法（特許公開、昭５２−４６０１８号
）が知られているが、操作が複雑になったり特殊な原料
を必要とするという欠点がある。更に改良法としてファ
ルネシル酢酸とゲラニオールをオルトギ酸エステル存在
下加熱号
する方法（特許公開、昭ｓ４−ｔｚａｓ１Ｍがあるが、
加熱を必要とし且回収不可能な反応促進剤を等モル使用
する必要がある。A known method for producing geranyl farnesyl acetate is a method in which geraniol and farnesyl acetate are refluxed in the presence of a catalyst such as sulfuric acid while removing water by azeotropy (
Patent Publication, No. 39-5619, Belgian Patent No. 617
No. 994), but this method has the drawbacks of low esterification yield and isomerization of the target product due to the esterification catalyst. As a method to improve these drawbacks, first, geraniol and boric acid are reacted to form an active ester, and then
Method for producing farnesyl acetate geranyl ester by reacting with farnesyl acetate (patent publication, 1983, 1983)
No. 8) or farnesyl acetic acid and geraniol. ．． E), J, Ayo, Neo, 7ke1. A method of reacting in the presence of acetal (Patent Publication No. 46018/1982) is known, but it has drawbacks such as complicated operations and the need for special raw materials. As a further improved method, there is a method of heating farnesyl acetic acid and geraniol in the presence of orthoformic acid ester (patent publication, S4-TZAS1M).
It is necessary to use equimolar amounts of reaction promoters that require heating and are not recoverable.
そこで、リパーゼのエステル合成反応を利用して温和な
条件下で上記エステルを合成することが考えられるが、
リパーゼが有機溶媒中に溶解しないため効率的に反応を
行うことができない。そのため有機溶媒に可溶でかつ酵
素活性を有する修飾リパーゼを用いた飽和アルコールと
飽和脂肪酸或いは不飽和アルコールと低級飽和脂肪酸と
のエステルの合成法が報告されている（特開昭６０＝１
５６３９５ 、Ｔ、Ｎ１５ｈｉｏ ｅｔ ａｌ、、 Ｂ
ｉｏｔｅｃｈｎｏｌｏｇｙＬｅｔｔｅｒｓ、 ９ 、
Ｎｕ ３． １８７−１９０． （１９８７）、）。Therefore, it is conceivable to synthesize the above ester under mild conditions using the ester synthesis reaction of lipase.
Since lipase does not dissolve in organic solvents, the reaction cannot be carried out efficiently. Therefore, a method for synthesizing esters of saturated alcohols and saturated fatty acids or unsaturated alcohols and lower saturated fatty acids using a modified lipase that is soluble in organic solvents and has enzymatic activity has been reported (Japanese Patent Application Laid-open No. 1983-11).
56395, T, N15hio et al,, B
iotechnology Letters, 9,
Nu 3. 187-190. (1987), ).
しかしながら、高級不飽和アルコールと高級不飽和脂肪
酸とのエステル合成法については全く言及されていない
。However, there is no mention of a method for synthesizing esters between higher unsaturated alcohols and higher unsaturated fatty acids.
本発明者らは、産業上有用なファルネシル酢酸ゲラニル
エステルを簡易に高収率で製造する方法を鋭意検討した
結果、１，１．１− ）リクロロエタン可溶性のＯ−メ
トキシポリエチレングリコール修飾リパーゼ酵素の存在
下において、ゲラニオールにファルネシル酢酸を温和な
条件で反応させることにより高純度なファルネシル酢酸
ゲラニルエステルを高収率で製造できることを見出し、
かかる知見に基いて本発明に到達したのである。As a result of intensive research into a method for easily producing industrially useful farnesyl geranyl acetate with high yield, the present inventors discovered that 1,1.1-) Lichloroethane-soluble O-methoxypolyethylene glycol-modified lipase enzyme We have discovered that highly pure farnesyl acetate geranyl ester can be produced in high yield by reacting geraniol with farnesyl acetate under mild conditions in the presence of
The present invention was arrived at based on this knowledge.
すなわち本発明は、０−メトキシポリエチレングリコー
ルで修飾されたリパーゼの存在下、１゜１．１−）ジク
ロロエタン中でゲラニオールにファルネシル酢酸を反応
させることを特徴とするファルネシル酢酸ゲラニルエス
テルの製造法を提供するものである。That is, the present invention provides a method for producing geranyl farnesyl acetate, which comprises reacting geraniol with farnesyl acetate in 1°1.1-) dichloroethane in the presence of a lipase modified with 0-methoxypolyethylene glycol. It is something to do.
本発明に用いる修飾リパーゼは、０−メトキシポリエチ
レングリコールの活性誘導体が、リパーゼ分子のアミノ
基に部分的に置換したものであって、特に２．４−ビス
−（Ｏ−メトキシポリエチレングリコール）−６−クロ
ロ−３−トリアジンでリパーゼ分子中のアミノ基の約２
５〜７５％が修飾されたものが好適に用いられる。修飾
率が２５％以下のリパーゼでは溶解性が低く、７５％以
上では酵素活性が低下する傾向にある。この修飾リパー
ゼの製造法は特開昭６０−１５６３９５号公報に記載さ
れている。The modified lipase used in the present invention is one in which the amino group of the lipase molecule is partially substituted with an active derivative of O-methoxypolyethylene glycol, and in particular, 2,4-bis-(O-methoxypolyethylene glycol)-6 -Chloro-3-triazine for about 2 amino groups in the lipase molecule
Those with 5 to 75% modification are preferably used. A lipase with a modification rate of 25% or less has low solubility, and a modification rate of 75% or more tends to reduce enzyme activity. A method for producing this modified lipase is described in JP-A-60-156395.
※
又リパーゼとしてはシュードモナス・フラボ２２ ・３
９ Ｂ （Ｐｓｅｕｄｏａ＋ｏｎａｓ−ｆｒａｇｉ ２
２ ・３９Ｂ）、シェードモナス・フルオレッセンス（
Ｐｓｅｕｄｏｍｏｎａｓ ８ｆｌｕｏｒｅｓｃｅｎｓ）
、カンディダ・シリンドラセア（Ｃａｎｄｉｄａ ｃｙ
ｌｉｎｄｒａｃｅａ）等由来のものを用いることができ
る。*Also, as a lipase, Pseudomonas flavo 22/3
9 B (Pseudoa+onas-fragi 2
2 ・39B), Shademonas fluorescens (
Pseudomonas 8fluorescens)
, Candida cylindracea
lindracea) and the like can be used.
本発明においては、溶媒として１，１．１−）リクロエ
タンを用いることが必須である（下記比較例参照）。１
，１．１−）リクロロエタンは無水〜含水状態のものを
用いることができる。受−の溶媒で本発明の反応に直接
関与しない溶媒を混合して用いることもできる。In the present invention, it is essential to use 1,1.1-)lichloethane as a solvent (see Comparative Example below). 1
, 1.1-) Anhydrous to hydrated dichloroethane can be used. A receiving solvent that does not directly participate in the reaction of the present invention can also be used in combination.
本発明の方法の実施に際し、ファルネシル酸とゲラニオ
ールを含む１，１．１−）リクロロエタンの溶液に上記
修飾リパーゼを加え、１０〜６０℃好ましくは特与室溢
で数時間〜数十時間攪拌して反応させるといったような
温和な条件で行われ、目的のファルネシル酢酸ゲラニル
エステルを高純度、かつ高収率で得ることができる。更
にこの修飾リパーゼは反応系にヘキサン等の非極性の有
機溶媒を加えて沈澱させることにより回収可能であり活
性を減することなく繰り返し使用できる。When carrying out the method of the present invention, the above-mentioned modified lipase is added to a solution of 1,1.1-)lichloroethane containing farnesylic acid and geraniol, and the mixture is stirred at 10 to 60°C, preferably overflowing in a special chamber, for several hours to several tens of hours. The reaction is carried out under mild conditions, such as a reaction with high purity, and the desired farnesyl acetate geranyl ester can be obtained with high purity and high yield. Furthermore, this modified lipase can be recovered by adding a non-polar organic solvent such as hexane to the reaction system to precipitate it, and can be used repeatedly without reducing its activity.
以下実施例を挙げて詳細に説明する。A detailed explanation will be given below with reference to examples.
〔実
施
例
１〕
ｈｅｘａｎｅ層は分取し溶媒留去した後、シリカゲルカ
ラムクロマトグラフィーで精製すると、ファルネシル酢
酸ゲラニルエステル（１６０■、８０％）を得た。ここ
で得たものは、ＮＭＲスペクトル及びガスクロマトグラ
フィーにおいて、市販品のファルネシル酢酸ゲラニルエ
ステルと同様の挙動を示した。[Example 1] The hexane layer was separated, the solvent was distilled off, and then purified by silica gel column chromatography to obtain farnesyl acetate geranyl ester (160 μm, 80%). The product obtained here exhibited behavior similar to commercial farnesyl acetate geranyl ester in NMR spectrum and gas chromatography.
ファルネシル酢酸（１３２Ｎ、０．５０ｍｍｏ １）及
びゲラニオール（７８■、０．５１ｍｍｏ １）の水飽
和１，１．１−）リクロロエタン（５，０ｍ１）溶液に
、Ｏ−メトキシポリエチレングリコール修飾、リパーゼ
（Ｐｓｅｕｄｏｍｏｎａｓ ｆｒａｇｉ ２２ ・３
９ Ｂ由来）酵素１０■（タンパク質量５■）を加え、
室温下で２４時間攪拌した。反応溶液の溶媒を留去し、
ｈｅｘａｎｅ （２Ｘ２５ｍｌ）を加え遠心により沈澱
物として該修飾酵素を回収した。A solution of farnesyl acetic acid (132 N, 0.50 mmo 1) and geraniol (78 μ, 0.51 mmo 1) in water-saturated 1,1.1-)lichloroethane (5,0 ml) was added with O-methoxypolyethylene glycol modification, lipase ( Pseudomonas fragi 22 ・3
9 B-derived) Add 10■ enzyme (protein amount 5■),
The mixture was stirred at room temperature for 24 hours. Distill the solvent of the reaction solution,
Hexane (2×25 ml) was added and the modified enzyme was collected as a precipitate by centrifugation.
〔実施例２〕 無水１，１．１−トリクロロエタンを用いてを得た。[Example 2] Obtained using anhydrous 1,1,1-trichloroethane.
〔実施例３〕 実施例２で回収した酵素を用い、実施例２と同■。[Example 3] Same procedure as in Example 2 using the enzyme recovered in Example 2.
８７％） を得た。87%) I got it.
〔実
施
例
４〕
実施例３の操作を４度繰り返した後に回収した〔実施例
６〕
０−メトキシポリエチレングリコール修飾リパーゼ酵素
５０．０■（タンパク質量２５．０■）を用い実施例２
と同様に反応を行った。反応時間及びファルネシル酢酸
ゲラニルエステルの収率を以下に記す。[Example 4] Collected after repeating the operation of Example 3 four times [Example 6] Example 2 using 0-methoxypolyethylene glycol modified lipase enzyme 50.0 μ (protein amount 25.0 μ)
The reaction was carried out in the same manner. The reaction time and the yield of farnesyl acetate geranyl ester are described below.
４時間 ７４％
７時間 ８２％
９時間 ８５％
１０時間 ８７％
Ｏ−メトキシポリエチレングリコール修飾リパーゼ酵素
２５．０■（タンパク質量１２．５■）を用い実施例２
と同様に反応を行い反応時間１８時間〔比 較 例〕4 hours 74% 7 hours 82% 9 hours 85% 10 hours 87% Example 2 using O-methoxypolyethylene glycol modified lipase enzyme 25.0■ (protein amount 12.5■)
The reaction was carried out in the same manner as above, and the reaction time was 18 hours [Comparative example]
Claims (1)
たリパーゼの存在下、１，１，１−トリクロロエタン中
でゲラニオールにファルネシル酢酸を反応させることを
特徴とするファルネシル酢酸ゲラニルエステルの製造法
。(1) A method for producing geranyl farnesyl acetate, which comprises reacting geraniol with farnesyl acetate in 1,1,1-trichloroethane in the presence of a lipase modified with O-methoxypolyethylene glycol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16882188A JPH0220289A (en) | 1988-07-08 | 1988-07-08 | Production of farnesylacetic acid geranyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16882188A JPH0220289A (en) | 1988-07-08 | 1988-07-08 | Production of farnesylacetic acid geranyl ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0220289A true JPH0220289A (en) | 1990-01-23 |
Family
ID=15875134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16882188A Pending JPH0220289A (en) | 1988-07-08 | 1988-07-08 | Production of farnesylacetic acid geranyl ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0220289A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0507278A2 (en) * | 1991-04-02 | 1992-10-07 | Hoechst Aktiengesellschaft | Immobilised biocatalyser, its preparation and use for ester synthesis in a column reactor |
-
1988
- 1988-07-08 JP JP16882188A patent/JPH0220289A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0507278A2 (en) * | 1991-04-02 | 1992-10-07 | Hoechst Aktiengesellschaft | Immobilised biocatalyser, its preparation and use for ester synthesis in a column reactor |
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