JPS59181244A - Optical resolution of dl-phenylalanine - Google Patents
Optical resolution of dl-phenylalanineInfo
- Publication number
- JPS59181244A JPS59181244A JP5167483A JP5167483A JPS59181244A JP S59181244 A JPS59181244 A JP S59181244A JP 5167483 A JP5167483 A JP 5167483A JP 5167483 A JP5167483 A JP 5167483A JP S59181244 A JPS59181244 A JP S59181244A
- Authority
- JP
- Japan
- Prior art keywords
- phenylalanine
- mandelic acid
- optically active
- optical resolution
- complex
- 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-UHFFFAOYSA-N phenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 230000003287 optical effect Effects 0.000 title claims abstract description 6
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229960002510 mandelic acid Drugs 0.000 claims abstract description 9
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 8
- 230000003187 abdominal effect Effects 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract description 20
- 229960005190 phenylalanine Drugs 0.000 abstract description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 5
- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 abstract description 3
- 229930182832 D-phenylalanine Natural products 0.000 abstract description 3
- 238000001816 cooling Methods 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 2
- 239000011707 mineral Substances 0.000 abstract description 2
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- ULGJWNIHLSLQPZ-UHFFFAOYSA-N 7-[(6,8-dichloro-1,2,3,4-tetrahydroacridin-9-yl)amino]-n-[2-(1h-indol-3-yl)ethyl]heptanamide Chemical compound C1CCCC2=NC3=CC(Cl)=CC(Cl)=C3C(NCCCCCCC(=O)NCCC=3C4=CC=CC=C4NC=3)=C21 ULGJWNIHLSLQPZ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 102000005367 Carboxypeptidases Human genes 0.000 description 1
- 108010006303 Carboxypeptidases Proteins 0.000 description 1
- -1 L-phenylalanine-d-mandelic acid Chemical compound 0.000 description 1
- CBQJSKKFNMDLON-UHFFFAOYSA-N N-acetylphenylalanine Chemical compound CC(=O)NC(C(O)=O)CC1=CC=CC=C1 CBQJSKKFNMDLON-UHFFFAOYSA-N 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 108010003977 aminoacylase I Proteins 0.000 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000004905 finger nail Anatomy 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- IKGHIFGXPVLPFD-UHFFFAOYSA-N methyl 2-acetamido-3-phenylpropanoate Chemical compound COC(=O)C(NC(C)=O)CC1=CC=CC=C1 IKGHIFGXPVLPFD-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002993 phenylalanine derivatives Chemical class 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、光学活性フェニルアラニンの製造に関するも
のである。し−フェニルアラニンは必要アミノ酸の１つ
であるが、これまで生産峻としては少なく、アミノ酸輸
夜等に用いられているの与であった。最近になり、アミ
ノ酸・論液用の漸増順向とともに１医薬品合成原料しよ
び人工甘味料であるα−Ｌ−アスパルチル−し一フェニ
ルアラニジメチルエステル（アスパルテーム）の原料と
して需要が高まりつつある。またＤ−フェニルアラニン
も′礪膚作用を持つなどから、大儀の光学活性フェニル
アラニンを細枠に単離する必要性−ｂ二生じてきた。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the production of optically active phenylalanine. Phenylalanine is one of the necessary amino acids, but until now it has been produced in small quantities and has only been used as an amino acid. Recently, with the gradual increase in the use of amino acids and logical liquids, demand has been increasing as a raw material for pharmaceutical synthesis and for the artificial sweetener α-L-aspartyl-phenylalanidimethyl ester (aspartame). Furthermore, since D-phenylalanine also has an inflammatory effect, there has been a need to isolate optically active phenylalanine in a small size.
ＤＬ−フェニルアラニンの光学分割（では多くの方法が
報告されている。１）ＤＬ−フェニルアラニンのＮ−ク
ロロアセチルｄ ４１本ＫＩ鯵・噸カルボキシペプチダ
ーゼを１乍用させ、酵素分割する方法（Ｊ 、 Ｂ 、
Ｇ１１ｂｅｒｔ、 Ｖ、 Ｂ。Optical resolution of DL-phenylalanine (Many methods have been reported. 1) A method of enzymatic resolution using one N-chloroacetyl d41 KI Aji-Kan carboxypeptidase of DL-phenylalanine (J, B ,
G11bert, V, B.
Ｐｒ１ｃｅ 、ａｎｄ Ｊ、Ｐ、Ｇｒｅｅｎｓｔｅ
ｉｎ、Ｊ。Pr1ce, and J., P., Greenste.
in, J.
Ｂｉｏｌ、 Ｃｈｅｍ、 、 １旦−Ｑ、、 ４７３
（１９４９）） ２） Ｎ−７セチルーＤＬフェ
ニルアラニンを糸状ｉアミノアシラーゼで不語加水分解
する方法（Ｔ、Ｔｏ、ｓａ、Ｔ、Ｍｏｒｉ、Ｎ、Ｆｕｓ
ｅ ａｎｄ Ｉ。Biol, Chem, 1dan-Q, 473
(1949)) 2) Method for hydrolyzing N-7 cetyl-DL phenylalanine with filamentous aminoacylase (T, To, sa, T, Mori, N, Fus
e and I.
Ｃｈｉｂａｔａ、 Ｂｉｏｔｅｃｈｎｏｌ、 Ｂｉ
ｏｅｎｇ、。Chibata, Biotechnol, Bi
oeng,.
９、 ６０３ （１９６７）） ３） Ｎ−アセ
チル−ＤＬ−フェニルアラニンメチルエステルニ蛋白質
分解酵素を作用させ子爪加水分解する方法（％公昭５７
−３５９５６） ｊ）Ｎ−アセチル−ＤＬ−フェニル
アラニンをアンモニウム頃として過砲仲水溶液より優先
晶、折させる物理化学的方法（特公昭３９−２４４４０
）などが仰られている。しかしながら、これら酵素的分
割方法あるいｉｄフェニルアラニン誘導体の分割以外に
直接的にフェニルアラニ／を分割した例１ｄ未だ報告さ
れていない。9, 603 (1967)) 3) Method of hydrolyzing finger nails by acting with N-acetyl-DL-phenylalanine methyl ester protease (% Kosho 57
-35956) j) Physicochemical method of preferentially crystallizing and folding N-acetyl-DL-phenylalanine from an aqueous solution using ammonium (Japanese Patent Publication No. 39-24440)
) etc. are said. However, no example 1d has yet been reported in which phenylalanine/ is directly resolved other than these enzymatic resolution methods or resolution of id phenylalanine derivatives.
一方、ＤＬ−マンデル酸に、Ｌ−フェニルアラニンを作
用させると、Ｌ−フェニルアラニン・Ｌ−マンデル酸複
合体が晶出するという報告（日化誌９’２．９９９ （
１９７１） ）があるが、Ｄし一フェニルアラニンが光
学活性なマンデル酸によって光学分前できるという報告
（は見当らない。On the other hand, it has been reported that when L-phenylalanine is allowed to act on DL-mandelic acid, an L-phenylalanine/L-mandelic acid complex crystallizes (Nichikkashi 9'2.999 (
(1971)), but there is no report that D-phenylalanine can be optically separated by optically active mandelic acid.
これらの事実に基づき、本発明番らは、工業的に加１更
かつ安価な光学活性フェニルアラニンの製造法を開＃、
ｔべく検討を重ねた結果、光学活性マンデル酸を用いる
ことｆこより、ＤＬ−フェニルアラニンを誘導体（（導
くことなく、高純度、商収率で置部光学分割できること
ｆ：見い出した。Based on these facts, the inventors of the present invention have developed a method for producing optically active phenylalanine that is industrially more processable and inexpensive.
As a result of repeated studies, it was discovered that by using optically active mandelic acid, DL-phenylalanine could be optically resolved into derivatives with high purity and commercial yield without derivation.
すなわち、本発明ｉｄ Ｄ Ｌ−フェニルアラニンに光
学活性なマンデル酸を作用させて複合体を形成し、その
溶！ｉ差を利用して光学分割する方法である。That is, the present invention id D L-phenylalanine is reacted with optically active mandelic acid to form a complex, and the complex is dissolved! This is a method of optical division using the i difference.
本発明の実ａ＆こあたっては、溶媒中でＤＬ−フェニル
アラニ／に光学活性マンテル酸を作用させて２つのジア
ステレオマー複合＋ｔｉ−全生成させ、その後金と１１
などの操作により・難溶性複合体を選択的に晶出させ、
１司液を分離してＬ−フェニルアラニン−し−マンデル
酸マｆｔＩ／１ｉＤ−フェニルアラニン−Ｄ−マン７
）しｒ曖ｆ：得る。生成した複合体は、鉱酸により分解
した淡、有・機ｌ各課でマンデル酸を抽出・除去し、ア
ルカリにより中和して光学活１生フェニルアラニ／を析
出させ、必要があればこれを再結晶して光学活性フェニ
ルアラニンを得ることができる。In the practice of the present invention, optically active mantelic acid is applied to DL-phenylalani/ in a solvent to form two diastereomer complexes +ti-, and then gold and 11
By such operations, the poorly soluble complex is selectively crystallized,
1 liquid was separated and L-phenylalanine-d-mandelic acid MAFTI/1iD-phenylalanine-D-man7
) し r vague f: obtain. The resulting complex is decomposed with mineral acid, and mandelic acid is extracted and removed in the organic and organic sections, neutralized with alkali to precipitate optically active phenylalanine, and if necessary, this is removed. Optically active phenylalanine can be obtained by recrystallization.
使用する溶媒としては、ＩＩｆｉ活、水、メタノール、
エタノール、１−プロパツール、２−プロパノールおよ
びこれらの溶媒の混合溶媒などが好ましい。The solvents used include IIfi active, water, methanol,
Ethanol, 1-propanol, 2-propanol, a mixed solvent of these solvents, and the like are preferred.
晶析させる際には、特に接種の必要ｌｒｉないが、晶析
を円管に行なうために難溶性複合体を敵酸加えても良い
。When performing crystallization, there is no particular need for inoculation, but enemy acid may be added to the poorly soluble complex in order to perform crystallization in a circular tube.
以下、実姉例を挙げ、本発明方法を詳細に説明する。Hereinafter, the method of the present invention will be explained in detail using a real sister example.
実施例１゜
水３６ ＋ｎｌにＤＬ−フェニルアラニン１６．５ＳＭ
’（０，１０ｍｏｌ）、Ｌ−（ト）−マンデル酸７．６
１ｇ （０，０５ｍｏｌ ）、メタンスルホン酸５．７
７１（０，０６ｍｏｌ）を加え、攪拌しつつ加温溶解シ
タ。７０℃にてＬ−フェニルアラニン・Ｌ−マンデル酸
複合体の種結晶（〔α〕４３５＋ １２０．８°）０．
Ｉｆを接種した。放冷後、同夜分離して、Ｌ−フェニル
アラニン・Ｌ−マノデル酸複合体１１．３６１を得た。Example 1 DL-phenylalanine 16.5 SM in 36 +nl of water
'(0.10 mol), L-(t)-mandelic acid 7.6
1g (0.05mol), methanesulfonic acid 5.7
Add 71 (0.06 mol) and dissolve while stirring. Seed crystals of L-phenylalanine/L-mandelic acid complex ([α]435+120.8°) 0.
If was inoculated. After cooling, it was separated on the same night to obtain L-phenylalanine/L-manoderic acid complex 11.361.
〔α〕４３５＋１２０．６° （ｃ １．０ 、 Ｈ
２０）この結晶を水３４ ｍｌより再結晶して、精製Ｌ
−フェニルアラニン・Ｌ−マンデル酸複合ｉ本６．５３
ＦｔｒＩ＆。Ｃαｌｊ ３−ｇ＋ｔ ２０．８゜（ｃ
１．０．Ｈ２Ｏ）
こうして得た晴委復合体を水１０ｒｎｌに加温溶解し、
濃塩酸を加えコンゴレッド凛：生とした。放冷後エーテ
ル抽出を行ない２．９４ ｆのし−（ト）−マ／デル：
瞳を回収した。〔α〕２０・５＋１５０．９° （ｃ
１．０．Ｈ２Ｏ）回収率９３．９チ
ニーチル抽出後の水層に６硯定水酸化ナトリウム水溶液
をｐＨ７になるまで加え、析出した し−（へ）−フェ
ニルアラニン２．３４ｒｉ得だ。〔α〕１９・５−２０
．９° （ｃｌ、０゜Ｈ２Ｏ）
このＬ−（ハ）−フェニルアラニンを１０ｍ１の水より
再結晶して、悄映し−（→−フェニルア特許出願人
山用薬品工栗昧式会社
代表取締役 取原識部[α]435+120.6° (c 1.0, H
20) Recrystallize this crystal from 34 ml of water to obtain purified L.
- Phenylalanine/L-mandelic acid complex i book 6.53
FtrI&. Cαlj 3-g+t 20.8° (c
1.0. H2O) The thus obtained clear polymer complex was dissolved in 10 rnl of water by heating,
Congo Red Rin was made raw by adding concentrated hydrochloric acid. After cooling, ether extraction was performed to obtain 2.94 f.
The eyes were recovered. [α]20・5+150.9° (c
1.0. H2O) recovery rate: 93.9 To the aqueous layer after extraction with chinychile, 6 ml of constant sodium hydroxide aqueous solution was added until the pH reached 7, and 2.34 ri of shi-(he)-phenylalanine was precipitated. [α] 19.5-20
．． 9° (cl, 0°H2O) This L-(c)-phenylalanine was recrystallized from 10 ml of water, and the crystallization - (→- Phenylua Patent Applicant
Shikibe Torihara, Representative Director of Yamayo Pharmaceutical Co., Ltd.
Claims (1)
用させ、生成した腹き体を、その溶解度差を利用して分
割することを特徴とするＤＬ−フェニルアラニンの光学
分割法An optical resolution method for DL-phenylalanine, which is characterized in that an optically active form of mandelic acid is applied to DL-phenylalanine, and the resulting abdominal bodies are separated by utilizing the difference in solubility thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5167483A JPS59181244A (en) | 1983-03-29 | 1983-03-29 | Optical resolution of dl-phenylalanine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5167483A JPS59181244A (en) | 1983-03-29 | 1983-03-29 | Optical resolution of dl-phenylalanine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS59181244A true JPS59181244A (en) | 1984-10-15 |
Family
ID=12893423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5167483A Pending JPS59181244A (en) | 1983-03-29 | 1983-03-29 | Optical resolution of dl-phenylalanine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59181244A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0158301A2 (en) * | 1984-04-06 | 1985-10-16 | Nippon Kayaku Kabushiki Kaisha | Process for producing optically active phenylalanine |
| JPS61115052A (en) * | 1984-11-08 | 1986-06-02 | Nippon Kayaku Co Ltd | Production of optically active mandelic acid |
| CN1301967C (en) * | 2004-12-15 | 2007-02-28 | 南京大学 | Method of chiral separation for D,L-phenylalanine ester or its salt |
-
1983
- 1983-03-29 JP JP5167483A patent/JPS59181244A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0158301A2 (en) * | 1984-04-06 | 1985-10-16 | Nippon Kayaku Kabushiki Kaisha | Process for producing optically active phenylalanine |
| JPS61115052A (en) * | 1984-11-08 | 1986-06-02 | Nippon Kayaku Co Ltd | Production of optically active mandelic acid |
| CN1301967C (en) * | 2004-12-15 | 2007-02-28 | 南京大学 | Method of chiral separation for D,L-phenylalanine ester or its salt |
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