JPH062070B2 - ▲ O --- Method for producing acylamino acid - Google Patents
▲ O --- Method for producing acylamino acidInfo
- Publication number
- JPH062070B2 JPH062070B2 JP16666788A JP16666788A JPH062070B2 JP H062070 B2 JPH062070 B2 JP H062070B2 JP 16666788 A JP16666788 A JP 16666788A JP 16666788 A JP16666788 A JP 16666788A JP H062070 B2 JPH062070 B2 JP H062070B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- oil
- homoserine
- serine
- 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.)
- Expired - Lifetime
Links
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、リパーゼの触媒能を利用して脂肪酸あるいは
油脂とヒドロキシアミノ酸から乳化力の高い界面活性物
質であるＯ−アシルアミノ酸を製造する方法に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention is a method for producing an O -acyl amino acid, which is a surface-active substance having high emulsifying power, from a fatty acid or a fat and an oil and a hydroxyamino acid by utilizing the catalytic activity of lipase. It is about.
〔従来の技術〕Ｏ −アシルアミノ酸は、公知の化学的合成法によって合
成できる。例えば、ヒドロキシアミノ酸をＮ−ｔ−ブト
キシカルボニル基で保護した後、脂肪酸塩化物をピリジ
ンの存在下有機溶媒中で反応させ保護基をはずすことに
よって合成される(G. V. Marinetti, Chem. Phys. Lipi
ds, 33, 145-152(1985))。[Prior Art] O -acyl amino acids can be synthesized by known chemical synthesis methods. For example, the hydroxy amino acid N - t -.. After protected butoxycarbonyl group, is synthesized by removing the protecting group by reacting a fatty acid chloride in the presence an organic solvent pyridine (GV Marinetti, Chem Phys Lipi
ds, 33, 145-152 (1985)).
〔発明が解決しようとする課題〕Ｏ −アシルアミノ酸は、既存の食用乳化剤であるグリセ
リン脂肪酸エステル，ソルビタン脂肪酸エステル，ショ
糖脂肪酸エステルなどの非イオン性界面活性物質とは異
なり、両イオン性の界面活性物質である。また、その構
成成分は天然にある物質であることから、従来のものに
はない新しい機能を持った安全性の高い食用乳化剤，食
品素材あるいは化粧品素材としての利用が期待される。
しかし、従来のＯ−アシルアミノ酸の化学的合成法は、
有機溶媒を溶いるので食品への利用のためには好ましく
ない。また、反応行程が複雑であるという欠点がある。[Problems to be Solved by the Invention] O -acyl amino acids are different from nonionic surface-active substances such as glycerin fatty acid ester, sorbitan fatty acid ester, and sucrose fatty acid ester, which are existing edible emulsifiers, in contrast to zwitterionic interfaces. It is an active substance. Further, since its constituent components are naturally occurring substances, it is expected to be used as a highly safe edible emulsifier, a food material or a cosmetic material having a new function which has not been found in the past.
However, the conventional chemical synthesis method of O -acyl amino acid is
Since it dissolves an organic solvent, it is not preferable for use in foods. Further, there is a drawback that the reaction process is complicated.
本発明は、有機溶媒を用いず、かつ簡単な反応系でＯ−
アシルアミノ酸を合成する方法を提供するためになされ
たものである。The present invention, O in without using an organic solvent, and simple reaction system -
It was made to provide a method for synthesizing an acylamino acid.
本発明者らは、上記の欠点を解消するため、Ｏ−アシル
アミノ酸の酵素的合成法について研究を行ったところ、
油脂あるいは脂肪酸とＬ−セリン，Ｌ−ホモセリン等の
ヒドロキシアミノ酸をリパーゼの存在下で反応させるこ
とにより有機溶媒を用いず、かつ簡単な反応系でＯ−ア
シル−Ｌ−セリン，Ｏ−アシル−Ｌ−ホモセリン等のＯ
−アシルアミノ酸を合成できることを発見し、本発明に
到達した。In order to solve the above-mentioned drawbacks, the present inventors have studied an enzymatic synthesis method of O -acyl amino acid,
O -acyl-L-serine, O -acyl-L can be obtained by reacting a fat or oil or a fatty acid with a hydroxyamino acid such as L-serine or L-homoserine in the presence of lipase in a simple reaction system without using an organic solvent. - O, such as homoserine
-Discovered that an acylamino acid can be synthesized and arrived at the present invention.
すなわち、本発明はＯ−アシルアミノ酸を製造するにあ
たり、油脂あるいは脂肪酸とＬ−セリンまたはＬ−ホモ
セリンをリパーゼの存在下で反応させることを特徴とす
るＯ−アシルアミノ酸の製造方法を提供するものであ
る。That is, the present invention is O - in producing the acylamino acid, O is the oil or fatty acid and L- serine or L- homoserine comprises reacting in the presence of a lipase - is provided a method for producing an acylamino acid is there.
本発明に用いる油脂としては、一般の動植物油脂のいず
れでもよく、具体例としては牛脂，豚脂，羊脂，魚油，
大豆油，コーン油、オリーブ油，ナタネ油，ヒマワリ
油，サフラワー油，ヤシ油，パーム油などを挙げること
ができる。The fat and oil used in the present invention may be any of general animal and vegetable fats and oils, and specific examples thereof include beef tallow, lard, sheep fat, fish oil,
Soybean oil, corn oil, olive oil, rapeseed oil, sunflower oil, safflower oil, coconut oil, palm oil and the like can be mentioned.
また、本発明に用いる脂肪酸としては、種々のものを使
用できるが、炭素数１２以上の長鎖の飽和あるいは不飽
和脂肪酸が適当である。その例としてはラウリン酸，ミ
リスチン酸，パルミチン酸，ステアリン酸，アラキン
酸，ベヘン酸，リンデル酸，ミリストレイン酸，パルミ
トオレイン酸，オレイン酸，ガドレイン酸，エルカ酸，
リノール酸，リノレン酸などを挙げることができる。As the fatty acid used in the present invention, various fatty acids can be used, but a long-chain saturated or unsaturated fatty acid having 12 or more carbon atoms is suitable. Examples include lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, linderic acid, myristoleic acid, palmitooleic acid, oleic acid, gadoleic acid, erucic acid,
Examples thereof include linoleic acid and linolenic acid.
反応液のＬ−セリンまたはＬ−ホモセリン濃度は飽和濃
度に近い高濃度とするのが好ましい。また、合成反応の
最適pHは７−８であるので、Ｌ−セリンまたはＬ−ホモ
セリン溶液のpHの緩衝液たとえばリン酸緩衝液、あるい
はアルカリなどで最適pHに調整しておくことが好まし
い。The L-serine or L-homoserine concentration in the reaction solution is preferably a high concentration close to the saturation concentration. Further, since the optimum pH of the synthesis reaction is 7-8, it is preferable to adjust the pH to an optimum pH with a buffer solution having a pH of L-serine or L-homoserine solution, such as a phosphate buffer, or an alkali.
リパーゼとしては、動植物起源のものや微生物起源のも
のがあるが、脂肪酸あるいは油脂とＬ−セリンまたはＬ
−ホモセリンからＯ−アシルアミノ酸を合成する能力を
有するものであればいずれでもよく、またその純度は問
題とはならない。Examples of lipase include those of animal and plant origin and those of microbial origin, and fatty acid or oil and L-serine or L
Any one may be used as long as it has the ability to synthesize an O -acyl amino acid from homoserine, and its purity does not matter.
反応は、リパーゼを含有するＬ−セリンまたはＬ−ホモ
セリン溶液に対し脂肪酸あるいは油脂を添加し、１〜４
８時間、好ましくは３〜２４時間、１０〜５０℃、好ま
しくは２０〜４０℃で激しく撹拌することによって行わ
れる。また、常温で固体の脂肪酸あるいは油脂を用いる
場合は、反応液にｎ−ヘキサン等の油脂を溶解する溶媒
を加えることによって効率よく反応を進めることができ
る。Ｌ−セリンまたはＬ−ホモセリン溶液と油脂あるい
は脂肪酸の量比は、撹拌によって両者が十分に混合する
ものであればよい。例えば、Ｌ−セリンまたはＬ−ホモ
セリン溶液１に対し油脂あるいは脂肪酸を10〜500
ｇ、好ましくは50〜200ｇを用いれば、撹拌によって十
分混合することができる。The reaction is carried out by adding a fatty acid or fat to a L-serine or L-homoserine solution containing lipase, and
It is carried out by vigorous stirring at 10 to 50 ° C, preferably 20 to 40 ° C for 8 hours, preferably 3 to 24 hours. When a fatty acid or fat or oil that is solid at room temperature is used, the reaction can be efficiently proceeded by adding a solvent such as n -hexane that dissolves the fat or oil to the reaction solution. The amount ratio of the L-serine or L-homoserine solution to the fat or oil or the fatty acid may be such that both are sufficiently mixed by stirring. For example, 1 to L-serine or L-homoserine solution is mixed with 10 to 500 oils or fatty acids.
If g, preferably 50 to 200 g is used, it can be sufficiently mixed by stirring.
反応終了後、反応液から溶媒抽出によってＯ−アシルア
ミノ酸を抽出し、次いで抽出物から常法、例えばシリカ
ゲルカラムクロマトグラフィーあるいは溶剤分別によっ
て高純度のＯ−アシルアミノ酸が得られる。After completion of the reaction, O by solvent extraction from the reaction solution - to extract the acylamino acid and then a conventional method from the extract, high purity O, for example, by silica gel column chromatography or solvent fractionation - acylamino acid obtained.
このように本発明によれば、人体に有害な有機溶媒を反
応系に用いず、単純な反応行程によりＯ−アシルアミノ
酸が得られる。As described above, according to the present invention, an O -acyl amino acid can be obtained by a simple reaction process without using an organic solvent harmful to the human body in the reaction system.
次に、実施例により本発明を説明する。 Next, the present invention will be described with reference to examples.
実施例１ リン酸緩衝液でpHを７．５に調整した３Ｍ Ｌ−ホモセ
リン溶液１mlに対しキャンディダ・シリンドラセ(Candi
da cylindracea)由来のリパーゼ（名糖産製，LIPASE M
Y,60,000 U/g）１０mgとオレイン酸１００mgを添加し、
３７℃で２４時間振とうし撹拌した。この反応により約
１．５mgのＯ−オレオイル−Ｌ−ホモセリンが生成し
た。生成物を反応混合液からクロロホルム：メタノール
（２：１、v/v）で抽出し、抽出物をケイ酸カラムで精
製することによって高純度Ｏ−オレオイル−Ｌ−ホモセ
リンを得た。Example 1 1 ml of a 3M L-homoserine solution whose pH was adjusted to 7.5 with a phosphate buffer solution was used to prepare Candi Sirindrace (Candi).
lipase from da cylindracea (manufactured by Meito Co., LIPASE M
Y, 60,000 U / g) 10 mg and oleic acid 100 mg,
The mixture was shaken and stirred at 37 ° C. for 24 hours. The reaction produced about 1.5 mg of O -oleoyl-L-homoserine. The product was extracted from the reaction mixture with chloroform: methanol (2: 1, v / v) and the extract was purified with a silicic acid column to give high purity O -oleoyl-L-homoserine.
実施例２ 実施例１において、オレイン酸の代わりにミリスチン
酸，パルミチン酸，ステアリン酸，パルミトオレイン
酸，リノール酸のいずれかを用い、反応時間を３時間と
したこと以外は実施例１と同様に反応させたところ、そ
れぞれ0.069mg，0.031mg，0.019mg，0.692mg，0.532mg
のＯ−アシル−Ｌ−ホモセリンを合成することができ
た。Example 2 Similar to Example 1 except that any one of myristic acid, palmitic acid, stearic acid, palmitooleic acid, and linoleic acid was used instead of oleic acid and the reaction time was 3 hours. When reacted with 0.069mg, 0.031mg, 0.019mg, 0.692mg, 0.532mg,
Of O -acyl-L-homoserine could be synthesized.
実施例３ 実施例１において、Ｌ−ホモセリンの代わりにＬ−セリ
ンを用い、反応時間を３時間としたこと以外は実施例１
と同様に反応させたところ、0.007mgのＯ−アシル−Ｌ
−セリンを合成することができた。Example 3 Example 1 was repeated except that L-serine was used instead of L-homoserine and the reaction time was 3 hours.
When reacted in the same manner as in 0.007 mg of O -acyl-L
-Serine could be synthesized.
実施例４ 実施例１において、オレイン酸の代わりに大豆油，コー
ン油，オリーブ油を用い、反応時間の３時間としたこと
以外は実施例１と同様に反応させたところ、それぞれ0.
715mg，0.705mg，0.740mgのＯ−アシル−Ｌ−ホモセリ
ンを合成することができた。Example 4 The reaction was performed in the same manner as in Example 1 except that soybean oil, corn oil and olive oil were used instead of oleic acid and the reaction time was 3 hours.
715 mg, 0.705 mg, 0.740 mg of O -acyl-L-homoserine could be synthesized.
本発明においては、合成原料である脂肪酸と油脂は天然
物であること、Ｌ−セリンはタンパク質の構成アミノ酸
であり、Ｌ−ホモセリンは植物、特に豆科植物に天然に
存在するアミノ酸であること、および合成は人体に有害
な試薬や溶媒を要しない酵素的合成法を用いていること
から、本発明によって合成されたＯ−アシルアミノ酸の
食用乳化剤としての安全性は十分信頼できる。また、従
来の合成食用乳化剤と異なり両イオン性である上に高い
乳化力を持つので、本発明によって合成されたＯ−アシ
ルアミノ酸は安全性の高い新規食用乳化剤，食品素材と
して食品工業の分野で利用が期待されるほか、化粧品等
の材料としての利用も考えられる。In the present invention, the fatty acids and fats and oils that are synthetic raw materials are natural products, L-serine is a constituent amino acid of protein, and L-homoserine is an amino acid naturally existing in plants, particularly legumes, Since the synthesis is performed by an enzymatic synthesis method which does not require reagents or solvents harmful to the human body, the safety of the O -acyl amino acid synthesized according to the present invention as an edible emulsifier is sufficiently reliable. Also, unlike conventional synthetic edible emulsifiers, since they are zwitterionic and have a high emulsifying power, the O -acyl amino acid synthesized according to the present invention is a highly safe novel edible emulsifier and food material in the field of food industry. Besides being expected to be used, it can also be used as a material for cosmetics and the like.
Claims (1)
脂肪酸あるいは油脂とＬ−セリンまたはＬ−ホモセリン
をリパーゼの存在下で反応させることを特徴とするＯ−
アシルアミノ酸の製造方法。1. When producing an O -acyl amino acid,
O- characterized by reacting a fatty acid or oil and fat with L-serine or L-homoserine in the presence of lipase
A method for producing an acylamino acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16666788A JPH062070B2 (en) | 1988-07-06 | 1988-07-06 | ▲ O --- Method for producing acylamino acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16666788A JPH062070B2 (en) | 1988-07-06 | 1988-07-06 | ▲ O --- Method for producing acylamino acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0217156A JPH0217156A (en) | 1990-01-22 |
| JPH062070B2 true JPH062070B2 (en) | 1994-01-12 |
Family
ID=15835496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16666788A Expired - Lifetime JPH062070B2 (en) | 1988-07-06 | 1988-07-06 | ▲ O --- Method for producing acylamino acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH062070B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL77081A (en) * | 1984-12-04 | 1999-10-28 | Genetics Inst | Dna sequence encoding human erythropoietin process for the preparation thereof and a pharmaceutical composition of human erythropoietin |
| JP3249147B2 (en) * | 1990-06-01 | 2002-01-21 | キリン−アムジエン・インコーポレーテツド | Oral preparation containing bioactive protein |
| US5431904A (en) * | 1993-09-09 | 1995-07-11 | The Gillette Company | O-acyl serines as deodorants |
| TW586933B (en) | 1996-06-20 | 2004-05-11 | Chugai Pharmaceutical Co Ltd | Compositions for treating liver-complaints using EPO |
-
1988
- 1988-07-06 JP JP16666788A patent/JPH062070B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0217156A (en) | 1990-01-22 |
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