JPS63203653A - Purification of phenylalanine - Google Patents
Purification of phenylalanineInfo
- Publication number
- JPS63203653A JPS63203653A JP3734687A JP3734687A JPS63203653A JP S63203653 A JPS63203653 A JP S63203653A JP 3734687 A JP3734687 A JP 3734687A JP 3734687 A JP3734687 A JP 3734687A JP S63203653 A JPS63203653 A JP S63203653A
- Authority
- JP
- Japan
- Prior art keywords
- phenylalanine
- organic solvent
- centrifugal force
- tyrosine
- liquid
- 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
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 title claims abstract description 33
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000000746 purification Methods 0.000 title abstract 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 239000012535 impurity Substances 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 238000005086 pumping Methods 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 abstract description 8
- 238000005194 fractionation Methods 0.000 abstract description 5
- 235000003599 food sweetener Nutrition 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000003765 sweetening agent Substances 0.000 abstract description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 4
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Landscapes
- 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
本発明はフェニルアラニンの新規ｎ製方法、詳しくは不
純物として少なくともチクシンを含むフェニルアラニン
をＮ製する方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 novel method for producing phenylalanine, and more particularly, to a method for producing phenylalanine containing at least thixin as an impurity.
フェニルアラニンはアミノ酸の一種であり医薬用に又、
アミノ酸系甘味料の原料として広く使用されている。Phenylalanine is a type of amino acid and is used for medicinal purposes.
It is widely used as a raw material for amino acid sweeteners.
従来の技術
フェニルアラニン及びチロシンは共通の構造的特徴とし
てベンゼン環を持つため物理的、化学的性質が極めてよ
く似ておシ相互分離は困難である。Prior Art Phenylalanine and tyrosine have a benzene ring as a common structural feature, and therefore have extremely similar physical and chemical properties, making it difficult to separate them from each other.
フェニルアラニン、チクシンの相互分離法としては吸着
樹脂を用いてフェニルアラニンのみを当該樹脂に吸着次
いで溶離する方法（特開昭６０−１３６５４３号公報参
照。）、フェニルアラニンのＮａ塩を用すた方法（特開
昭６０−１３７４６号公報参照。）等が知られているが
、前者は樹脂の再生、劣化の点で、後者はＮａＯＨを大
量に使用する点で問題がある。Methods for mutually separating phenylalanine and thixin include a method in which only phenylalanine is adsorbed onto the adsorption resin and then eluted (see JP-A-60-136543), a method using Na salt of phenylalanine (in JP-A-60-136543); (See Publication No. 60-13746.) etc., but the former has problems in terms of regeneration and deterioration of the resin, and the latter has problems in that it uses a large amount of NaOH.
発明が解決しようとする問題点
前記問題点を有さないような簡便かつ低コストでフェニ
ルアラニンとチクシンを相互分離できる方法の開発が望
まれている。Problems to be Solved by the Invention It is desired to develop a simple and low-cost method for mutually separating phenylalanine and thixin that does not have the above-mentioned problems.
るフェニルアラニンから チロシン１
分離し、精製する方法の開発を目的として鋭意検討を重
ねた結果、疎水性の大きいフェニルアラニンを有機溶媒
に抽出することによシチａシンと相互分離でき、上記目
的を達成できることを見出し、この発見に基き本発明を
完成するに到った。from phenylalanine to tyrosine 1
As a result of extensive research aimed at developing a method for separating and purifying it, we discovered that phenylalanine, which is highly hydrophobic, can be separated from cythiasine by extracting it into an organic solvent, and that the above objective can be achieved. Based on this, we have completed the present invention.
即ち、本発明は少なくともチクシンを不純物として夾雑
するフェニルアラニンの水溶液からフェニルアラニンを
ｙｎｔ製するに際し、遠心力で保持されたフェニルアラ
ニンの水溶液中に、水に対して分局する有機溶媒（水飽
和）を遠心力に抗して加圧送液し、フェニルアラニンを
有機溶媒に抽出することを特徴とするフェニルアラニン
のｎｆＪ１方法である。That is, in the present invention, when producing phenylalanine from an aqueous solution of phenylalanine that is contaminated with at least thixin as an impurity, an organic solvent (saturated with water) that is separated from water is added to the aqueous solution of phenylalanine that is held by centrifugal force. This is the nfJ1 method for phenylalanine, which is characterized in that phenylalanine is extracted into an organic solvent by pumping the liquid under pressure against the pressure.
本発明の出発物質として使用するフェニルアラニンは不
純物として少なくともチロシンを含むものであればよく
、その他の７ｉノ酸や不純物を含んでいても良い。Phenylalanine used as a starting material in the present invention may contain at least tyrosine as an impurity, and may contain other 7i acids or impurities.
本発明は少なくともチロシンが混合するフェニルアラニ
ン含有溶液中からフェニルアラニンを含む両分とチロシ
ンを含む画分とを分離する方法であシ、本発明の実施に
よりその他のアミノ酸、不純物がフェニルアラニン画分
又は他の画分に残ったとしても、従来の既知の技術で容
易にそれら不純物を分離できる。The present invention is a method for separating both the phenylalanine-containing fraction and the tyrosine-containing fraction from a phenylalanine-containing solution in which at least tyrosine is mixed. Even if they remain in the fraction, these impurities can be easily separated using conventional known techniques.
得られたチロシンを含む両分は、例えばチロシ本発明は
、多段液液分配分画装置を使用するのが便利である。こ
れは従来の向流分配分画装−１液滴向流分配装圓ではな
くて、遠心力を利用した連続液液分配分画装置である、
この装置は遠心力を利用する点で水性二相分配液を用い
る連）多段分配分画装置として他の装置より有利になる
。The obtained tyrosine-containing fraction is, for example, tyrosine.In the present invention, it is convenient to use a multi-stage liquid-liquid distribution fractionation device. This is a continuous liquid-liquid distribution fractionation device that utilizes centrifugal force, rather than the conventional countercurrent distribution fractionation device-1 droplet countercurrent distribution device.This device utilizes centrifugal force. It is more advantageous than other devices as a multi-stage distribution/fractionation device using phase partition liquids.
この装置の原理について述べる。遠心ローター上に分配
管を配列し、固定相としてアミノ酸混合液相を充填し、
遠心力で保持させる。一方移動相として溶媒（水飽和）
をローターの一端から固定相中へ連続的に加圧送液する
。The principle of this device will be described below. Arrange the distribution tubes on a centrifugal rotor, fill them with an amino acid mixed liquid phase as a stationary phase,
It is held by centrifugal force. Solvent (water saturated) as mobile phase
is continuously pumped into the stationary phase from one end of the rotor under pressure.
移動相液は固定相液中を遠心力の作用を受は微細な液滴
となって順次通過し１回転軸側の端から流出する。この
移動相液中に注入された試料成分は液液分配によシ分離
され分画採集される。The mobile phase liquid passes through the stationary phase liquid sequentially in the form of fine droplets under the action of centrifugal force, and flows out from the end on the one-rotation shaft side. The sample components injected into this mobile phase liquid are separated by liquid-liquid distribution and collected in fractions.
フェニルアラニン含有液の液性について述べる。The properties of the phenylalanine-containing liquid will be described.
フェニルアラニンは中性では溶解度は２ （ＩＡＣＩＪ
９Ｈ２０＞しか持たないため、フェニルアラニン含有溶
液のμｌは好ましくは、処理量を多くする点から酸（塩
酸、硫酸等）を加えて１０〜２０ Ｖｄノまで濃度を上
げたー二１〜２が良い。Phenylalanine has a solubility of 2 in neutral conditions (IACIJ
9H20>, the phenylalanine-containing solution preferably has a concentration of 1 to 2 μl by adding an acid (hydrochloric acid, sulfuric acid, etc.) to a concentration of 10 to 20 Vd in order to increase the throughput. .
また、酸性にした方がアミノ酸の分配率が高くなる点で
有利である。Furthermore, acidity is advantageous in that the distribution ratio of amino acids is higher.
フェニルアラニン含有液の負荷重は遠心クーターの容量
（理論段）、及び不純物のｉｔ／Ｃよって制限されるの
で最適条件を求める必要がある。Since the load weight of the phenylalanine-containing liquid is limited by the capacity of the centrifugal cooler (theoretical plate) and the it/C of impurities, it is necessary to find optimal conditions.
実施例 以下、実施例により本発明の詳細な説明する。Example Hereinafter, the present invention will be explained in detail with reference to Examples.
実施例１
下記に示す組成のアミノ酸混合物の水溶液九ついて、三
鬼エンデニアリング（株＞ｍ遠心液液分配クロマトグラ
フィーシステムモデルＩＭＴＰ −００１を使用し、遠
心液液分配クロマトグラフィーを実施した。Example 1 Nine aqueous solutions of amino acid mixtures having the compositions shown below were subjected to centrifugal liquid-liquid partition chromatography using a centrifugal liquid-liquid partition chromatography system model IMTP-001 manufactured by Miki Endeneering Co., Ltd.
結果は泥１図の如くである。The result is as shown in Figure 1.
（実験条件）
（試料組成）
（分析方法）
日立８３５型アミノ酸アナライザー使用にンヒドリン発
色）
発明の効果
前記から明らかな如く１本発明によれば簡便に７エニル
アラニンとチロシンを相互に分離することができるので
、本発明は工業止金めで有用である。(Experimental conditions) (Sample composition) (Analysis method) Nhydrin color development using Hitachi 835 type amino acid analyzer) Effects of the invention As is clear from the above, according to the present invention, 7-enylalanine and tyrosine can be easily separated from each other. This makes the present invention useful in industrial fasteners.
ｍ１図は前記実施例１の結果を口承したものである。
イ：正溶出；ロ：反転溶出
特許出邸人 味の素株式会社
第１図
溶 出 量
手続補正書
１、事件の表示
昭和６２年特許願第３７３４６号
２、発明の名称
フェニルアラニンのＭ製方法
３、補正をする者
事件との関係 特許出願人
住所 東京都中央区京橋−丁目５番８号代表者
取締役社長 歌 １）勝 弘 ＼゛４、補正指令の
日付 自発
５、補正により増加する発明の数 なし６、補正の
対象 明細書の発明の詳細な説明の欄７、補正の内
容Figure m1 is based on the results of Example 1 described above. A: Positive elution; B: Reverse elution patent owner Ajinomoto Co., Ltd. Figure 1 Elution amount procedure amendment 1, case description 1988 Patent Application No. 37346 2, title of invention Method for producing M of phenylalanine 3, Relationship with the case of the person making the amendment Patent applicant address: 5-8 Kyobashi-chome, Chuo-ku, Tokyo Representative
President and CEO Uta 1) Katsuhiro ＼゛4. Date of amendment order Voluntary action 5. Number of inventions increased by amendment None 6. Subject of amendment Column 7 for detailed explanation of the invention in the specification 7. Contents of amendment
Claims (1)
ラニンを精製するに際し、遠心力で保持された前記フェ
ニルアラニン含有水溶液中に、水に対し分層する有機溶
媒（水飽和）を遠心力に抗して加圧送液し有機溶媒中に
フェニルアラニンを抽出することを特徴とするフェニル
アラニン精製方法。 ２、有機溶媒が炭素数３〜４のアルコールである特許請
求の範囲第１項記載の方法。[Claims] 1. When purifying phenylalanine containing at least tyrosine as an impurity, an organic solvent (saturated with water) that separates into layers from water is added to the phenylalanine-containing aqueous solution held by centrifugal force against centrifugal force. A method for purifying phenylalanine, which comprises extracting phenylalanine into an organic solvent by pumping the liquid under pressure. 2. The method according to claim 1, wherein the organic solvent is an alcohol having 3 to 4 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3734687A JPS63203653A (en) | 1987-02-20 | 1987-02-20 | Purification of phenylalanine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3734687A JPS63203653A (en) | 1987-02-20 | 1987-02-20 | Purification of phenylalanine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63203653A true JPS63203653A (en) | 1988-08-23 |
Family
ID=12495017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3734687A Pending JPS63203653A (en) | 1987-02-20 | 1987-02-20 | Purification of phenylalanine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63203653A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100285236B1 (en) * | 1999-01-18 | 2001-03-15 | 김효근 | Separation and Purification Methods for Phenylalanine by Electrodialysis |
| EP1300392A4 (en) * | 2000-05-18 | 2005-11-23 | Mitsubishi Rayon Co | PROCESS FOR THE PRODUCTION OF OPTICALLY ACTIVE ALPHA AMINOIC ACID AND OPTICALLY ACTIVE ALPHA AMINO ACID AMID |
-
1987
- 1987-02-20 JP JP3734687A patent/JPS63203653A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100285236B1 (en) * | 1999-01-18 | 2001-03-15 | 김효근 | Separation and Purification Methods for Phenylalanine by Electrodialysis |
| EP1300392A4 (en) * | 2000-05-18 | 2005-11-23 | Mitsubishi Rayon Co | PROCESS FOR THE PRODUCTION OF OPTICALLY ACTIVE ALPHA AMINOIC ACID AND OPTICALLY ACTIVE ALPHA AMINO ACID AMID |
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