JPS6328061B2 - - Google Patents
Info
- Publication number
- JPS6328061B2 JPS6328061B2 JP3346980A JP3346980A JPS6328061B2 JP S6328061 B2 JPS6328061 B2 JP S6328061B2 JP 3346980 A JP3346980 A JP 3346980A JP 3346980 A JP3346980 A JP 3346980A JP S6328061 B2 JPS6328061 B2 JP S6328061B2
- Authority
- JP
- Japan
- Prior art keywords
- isoleucine
- hydrochloric acid
- resin
- exchange resin
- cation exchange
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 22
- 229960000310 isoleucine Drugs 0.000 claims description 19
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 18
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 13
- 229930182844 L-isoleucine Natural products 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 239000003729 cation exchange resin Substances 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 8
- 229940024606 amino acid Drugs 0.000 claims description 7
- 150000001413 amino acids Chemical class 0.000 claims description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 238000000855 fermentation Methods 0.000 description 4
- 230000004151 fermentation Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000012228 culture supernatant Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical compound CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 description 1
- AYFVYJQAPQTCCC-STHAYSLISA-N D-threonine Chemical compound C[C@H](O)[C@@H](N)C(O)=O AYFVYJQAPQTCCC-STHAYSLISA-N 0.000 description 1
- 229930182822 D-threonine Natural products 0.000 description 1
- 150000008543 L-isoleucines Chemical class 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 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
Description
【発明の詳細な説明】
本発明はＬ−イソロイシン〔以下（）と略称
する〕とDL−α−アミノ酪酸〔以下（）と略
称する〕の混合水溶液より（）を分離する方法
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for separating () from a mixed aqueous solution of L-isoleucine (hereinafter referred to as ()) and DL-α-aminobutyric acid (hereinafter referred to as ()).
本発明の目的は醗酵法により（）を前駆前と
して（）を製造した（）と（）を含む培養
液より（）を有利に分離精製するにある。 An object of the present invention is to advantageously separate and purify () from a culture solution containing () and (), which have been produced by a fermentation method using () as a precursor.
（）は必須アミノ酸として人間及び動物の栄
養上重要な役割をするアミノ酸であり、医薬、食
品、飼料強化剤としての需要は近年急激に増加し
つつある。（）は古くは蛋白質の加水分解物よ
り分離精製されていたが最近（）やＤ−スレオ
ニンを前駆体とする醗酵法が確立され、醗酵液中
に生成された（）を分離精製することが行われ
ている。しかしながら生成された（）と醗酵液
中に残存する（）の両方を含有する醗酵終了液
中より（）を好収量で分離精製することは従来
の技術では工業的に困難であり、良い工業的な方
法が強く要望されている。 () is an amino acid that plays an important role in the nutrition of humans and animals as an essential amino acid, and the demand for it as a medicine, food, and feed fortifier has been increasing rapidly in recent years. In the past, () was separated and purified from a protein hydrolyzate, but recently a fermentation method using () and D-threonine as a precursor has been established, making it possible to separate and purify () produced in the fermentation liquid. It is being done. However, it is industrially difficult to separate and purify () in a good yield from the fermentation-finished liquid containing both () produced and () remaining in the fermentation liquid using conventional techniques. A method is strongly desired.
従来一般的にイオン交換樹脂クロマトグラフイ
ーがアミノ酸の分離精製法として用いられてい
る。この方法は例えば実験農芸化学下巻445〜452
頁東京大学農学部農芸化学教室編 朝倉書店（昭
和44年度版）に記載されている。然しながら従来
用いられているこの技術は複雑な操作を要するこ
となどから、大量処理を必要とする工業的方法に
は好ましくない。 Conventionally, ion exchange resin chromatography has been generally used as a method for separating and purifying amino acids. This method can be used, for example, in Experimental Agricultural Chemistry Volume 2, 445-452.
Page edited by Department of Agricultural Chemistry, Faculty of Agriculture, University of Tokyo, Asakura Shoten (1964 edition). However, since this conventionally used technique requires complicated operations, it is not suitable for industrial methods requiring large-scale processing.
（）と（）の分離にイオン交換樹脂カラム
クロマトグラフイーが用いられた例として「日本
農芸化学会誌 第36巻、437〜441頁 1962年」が
ある。この方法では（）と（）の分離が悪く
効率的な分離法とは言えない。又この場合は
（）は１規定の塩酸水溶液により溶出される為
強い耐酸の器材を使用しなければならない。又こ
の溶出液より純品の（）を得るには塩酸を除く
必要がある。この為には、濃縮やイオン交換樹脂
処理が必要で使用機器の材質の問題があり且手法
が複雑となる難点がある。 An example of using ion exchange resin column chromatography to separate () and () is ``Journal of the Japanese Society of Agricultural Chemistry, Vol. 36, pp. 437-441, 1962.'' This method does not separate () and (), and cannot be said to be an efficient separation method. In this case, since () is eluted by a 1N hydrochloric acid aqueous solution, strong acid-resistant equipment must be used. Furthermore, in order to obtain pure () from this eluate, it is necessary to remove the hydrochloric acid. For this purpose, concentration and ion exchange resin treatment are required, and there are problems with the materials of the equipment used and the method is complicated.
本発明者は鋭意研究を行つて（）と（）の
共存する水溶液から（）を分離する為に次の様
な方法を見出し本発明に到達した。 The present inventor conducted extensive research and discovered the following method for separating () from an aqueous solution in which () and () coexist, and arrived at the present invention.
即ち、強酸性陽イオン交換樹脂（ダイヤイオン
SK−1BSやダウエツクス50Wなど）を充填した
樹脂塔に（）と（）の混在する水溶液を貫流
して液中の両アミノ酸を該樹脂に吸着せしめ、樹
脂層内の非吸着物質を脱イオン水にて洗滌した後
に0.02〜0.6特に好ましくは0.05〜0.07規定の希塩
酸を貫流することにより、先ず（）を選択的に
十分溶出せしめることが出来る。その際のSVは
２前後が望ましい。又樹脂塔の形はＬ／Ｄ４が
好ましい。（）が実質的に全て溶出された後希
塩酸の貫流を続けて（）が溶出し始めるのに若
干の余裕があるが、この間に希塩酸の貫流を終
え、脱イオン水を貫流して樹脂内の塩酸を洗滌
後、次に希アンモニア水を樹脂塔内に貫流するこ
とにより（）を（）とは別個に溶出し（）
と（）とを分離することができる。 In other words, strongly acidic cation exchange resin (Diaion
An aqueous solution containing a mixture of () and () is passed through a resin column filled with (SK-1BS, Dowex 50W, etc.) to adsorb both amino acids in the solution to the resin, and the non-adsorbed substances in the resin layer are removed by deionized water. By flowing dilute hydrochloric acid of 0.02 to 0.6N, particularly preferably 0.05 to 0.07N, after washing, () can be selectively and sufficiently eluted. In this case, the SV is preferably around 2. The shape of the resin tower is preferably L/D4. After substantially all of () has been eluted, dilute hydrochloric acid is continued to flow through, and there is a slight margin for () to begin to elute. During this time, diluted hydrochloric acid has finished flowing through, and deionized water is flowed through to remove the inside of the resin. After washing away the hydrochloric acid, dilute ammonia water is passed through the resin column to elute () separately from ().
and () can be separated.
希アンモニア水で溶出された（）の溶液は濃
縮するとアンモニアがガス状で放出され（）を
結晶化することが出来る。この濃縮工程はアルカ
リ性である為塩酸水溶液中で（）を濃縮する前
記の農芸化学会誌第36巻に記載されている方法
（以下この方法を旧法と呼ぶ）の様に耐酸機器を
使用する必要もなく非常に有利である。次に旧法
と本発明の実施例１の方法につき培養液よりイソ
ロイシンを精製する流れを示す。 When the solution of () eluted with dilute ammonia water is concentrated, ammonia is released in gaseous form and () can be crystallized. Since this concentration process is alkaline, it is also necessary to use acid-resistant equipment, as in the method described in Volume 36 of the Journal of the Japanese Society of Agricultural Chemistry (hereinafter referred to as the old method), in which () is concentrated in an aqueous hydrochloric acid solution. It is extremely advantageous. Next, the flow of purifying isoleucine from the culture solution using the old method and the method of Example 1 of the present invention will be shown.
旧 法
培養液9.2（イソロイシン17.2ｇ含有）
↓
強酸性陽イオン交換樹脂（内径7.4×高さ61cm）
↓アンモニア水
溶出液
↓濃縮メタノール添加
粗結晶
↓再溶解
濃縮液
↓
強酸性陽イオン交換樹脂
（内径2.3×高さ57cm
〃 1.6×〃 40cm）直列
↓1.0規定塩酸
イソロイシン画分溶出液
↓濃縮
アンバーライトIR4B OH型（中和）
↓濃縮
結晶
↓溶解
濃縮液
↓濃縮
再結晶（Ｌ−イソロイシン
11.2ｇ収量65％）
本発明実施例 １
培養液200ml（イソロイシン3.0ｇ含有）
↓
強酸性陽イオン交換樹脂（内径3.5×高さ21cm）
↓0.06規定希塩酸 ↓２％Ｗ／Ｖアンモニア水
溶出液（） 溶出液（）
↓ ↓濃縮
棄てる 結晶（イソロイシン
2.72ｇ収量90.6ｇ）
〔注；溶出液（）の操作の後溶出液（）の操
作を行う〕
以上２つの流れを比較すると、旧法は培養液上
澄を一度脱塩処理後に更に分画の必要があるが、
本発明の方法は一段処理が可能であつて、旧法に
対し本発明の方法によるものが流れが簡単であり
且イソロイシンの収量が優れていることが明らか
である。Old method Culture solution 9.2 (contains 17.2g of isoleucine) ↓ Strongly acidic cation exchange resin (inner diameter 7.4 x height 61cm) ↓ Ammonia water Eluate ↓ Concentrated methanol added Crude crystals ↓ Redissolve Concentrate ↓ Strongly acidic cation exchange resin ( Inner diameter 2.3 x height 57cm (1.6 x 40cm) in series ↓1.0N hydrochloric acid Isoleucine fraction eluate ↓Concentration Amberlite IR4B OH type (neutralization) ↓Concentration Crystal ↓Dissolution Concentrate ↓Concentration Recrystallization (L-isoleucine
11.2g yield 65%) Example 1 of the present invention 200ml of culture solution (contains 3.0g of isoleucine) ↓ Strongly acidic cation exchange resin (inner diameter 3.5 x height 21cm) ↓ 0.06N dilute hydrochloric acid ↓ 2% W/V aqueous ammonia eluate ( ) Eluate () ↓ ↓Concentrate and discard Crystals (isoleucine
2.72g Yield: 90.6g) [Note: Perform the eluate () operation after the eluate () operation.] Comparing the above two processes, the old method desalted the culture supernatant and then further fractionated it. Although it is necessary,
It is clear that the method of the present invention allows one-step processing, and that the method of the present invention has a simpler flow and a superior yield of isoleucine compared to the old method.
実施例 １
強酸性陽イオン交換樹脂のダイヤイオンSK−
1BS200mlを、内径35mm、長さ250mmのガラス円筒
管に充填し、10％Ｗ／Ｖ塩酸水溶液を200ml貫流
してＨ型の再生後400mlの脱イオン水を流速SV＝
１で流して充分水洗し、残在塩酸の完全除去を確
認する。次に醗酵終了液より菌体を除いた培養液
上澄（液中にＬ−イソロイシン15mg／ml、DL−
α−アミノ酪酸４mg／ml含有）400ml（PH4.0）を
前記陽イオン交換樹脂に貫流（流速SV＝１）し、
液中の両アミノ酸を吸着させた。その後800mlの
脱イオン水にて水洗（流速SV＝１）後0.06規定
塩酸水溶液を流速SV＝２にて貫流すると約1.2
貫流時より2.3貫流時までにDL−α−アミノ酪
酸の殆ど全量がＬ−イソロイシンを伴うことなく
溶出された。次に脱イオン水400mlにて水洗（流
速SV＝２）後２％Ｗ／Ｖアンモニア水溶液を流
速SV＝１にて貫流し、Ｌ−イソロイシンを溶出
させた。このＬ−イソロイシン画分を減圧濃縮純
品化することにより、Ｌ−イソロイシンの結晶
2.72ｇを得た。Example 1 Strongly acidic cation exchange resin Diamond SK-
Fill a glass cylindrical tube with an inner diameter of 35 mm and a length of 250 mm with 200 ml of 1BS, and after 200 ml of 10% W/V hydrochloric acid aqueous solution flows through it to regenerate the H type, 400 ml of deionized water is added at a flow rate of SV=
Rinse thoroughly with water and confirm complete removal of residual hydrochloric acid. Next, the culture supernatant after removing the bacterial cells from the fermentation-finished liquid (L-isoleucine 15 mg/ml, DL-
Flowing 400 ml (PH 4.0) of α-aminobutyric acid (containing 4 mg/ml) through the cation exchange resin (flow rate SV = 1),
Both amino acids in the liquid were adsorbed. After washing with 800 ml of deionized water (flow rate SV = 1), 0.06N hydrochloric acid aqueous solution is passed through at a flow rate SV = 2. Approximately 1.2
Almost the entire amount of DL-α-aminobutyric acid was eluted without accompanying L-isoleucine from the time of flow through to the time of 2.3 flow through. Next, after washing with 400 ml of deionized water (flow rate SV=2), a 2% W/V ammonia aqueous solution was passed through at a flow rate SV=1 to elute L-isoleucine. By concentrating and purifying this L-isoleucine fraction under reduced pressure, crystals of L-isoleucine are obtained.
2.72g was obtained.
添付の第１図は強酸性陽イオン交換樹脂に吸着
された培養終了液中のDL−α−アミノ酪酸とＬ
−イソロイシンを0.06規定の塩酸で溶出した場合
の溶出パターンを示す図である。使用した強酸性
陽イオン交換樹脂はダイヤイオンSK−1BS200ml
である。この樹脂を内径35mm長さ250mmの円筒ガ
ラス管に充填したものを樹脂塔として、実施例１
と同じ上記両アミノ酸の混合水溶液200mlを貫流
して該両アミノ酸の樹脂に吸着させ、次に樹脂塔
に0.06規定の塩酸をSV＝２で貫流して両アミノ
酸を溶出した結果が図示されている。 The attached Figure 1 shows the relationship between DL-α-aminobutyric acid and L
- It is a figure showing the elution pattern when isoleucine is eluted with 0.06N hydrochloric acid. The strongly acidic cation exchange resin used was Diaion SK-1BS 200ml.
It is. Example 1 A cylindrical glass tube with an inner diameter of 35 mm and a length of 250 mm was filled with this resin as a resin tower.
The figure shows the results of flowing 200 ml of the same mixed aqueous solution of both of the above amino acids and adsorbing them onto the resin, and then flowing 0.06N hydrochloric acid through the resin tower at SV = 2 to elute both amino acids. .
添付の第２図は第１図の場合において、0.06規
定塩酸の代りに１規定塩酸で溶出した場合のパタ
ーン図である。（１段処理では全く分離されな
い。） The attached FIG. 2 is a pattern diagram when eluting with 1N hydrochloric acid instead of 0.06N hydrochloric acid in the case of FIG. 1. (One-stage processing does not separate them at all.)
第１図は強酸性陽イオン交換樹脂に吸着された
DL−α−アミノ酪酸（）とＬ−イソロイシン
（）を0.06規定の塩酸で溶出した場合の溶出パ
ターンを示す図である。第２図は強酸性陽イオン
交換樹脂に吸着されたDL−α−アミノ酪酸
（）、イソロイシン（）を１規定の塩酸で溶出
した場合の溶出パターンを示す図である。ただ
し、両図共横軸は溶出量を示す。
Figure 1 shows the adsorption on a strongly acidic cation exchange resin.
It is a figure showing the elution pattern when DL-α-aminobutyric acid () and L-isoleucine () were eluted with 0.06 normal hydrochloric acid. FIG. 2 is a diagram showing an elution pattern when DL-α-aminobutyric acid ( ) and isoleucine ( ) adsorbed on a strongly acidic cation exchange resin were eluted with 1N hydrochloric acid. However, in both figures, the horizontal axis indicates the elution amount.
Claims (1)
含む混合水溶液を強酸性陽イオン交換樹脂に貫流
して両アミノ酸を該樹脂に吸着せしめた後先ず
0.02〜0.6規定の希塩酸水溶液にてDL−α−アミ
ノ酪酸を溶出し次にアンモニア水でＬ−イソロイ
シンを溶出することを特徴とするＬ−イソロイシ
ンをDL−α−アミノ酪酸より分離する方法。1. After flowing a mixed aqueous solution containing L-isoleucine and DL-α-aminobutyric acid through a strongly acidic cation exchange resin to adsorb both amino acids onto the resin,
A method for separating L-isoleucine from DL-α-aminobutyric acid, which comprises eluting DL-α-aminobutyric acid with a dilute aqueous hydrochloric acid solution of 0.02 to 0.6 normal, and then eluting L-isoleucine with aqueous ammonia.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3346980A JPS56131550A (en) | 1980-03-18 | 1980-03-18 | Separation of l-isoleucine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3346980A JPS56131550A (en) | 1980-03-18 | 1980-03-18 | Separation of l-isoleucine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56131550A JPS56131550A (en) | 1981-10-15 |
| JPS6328061B2 true JPS6328061B2 (en) | 1988-06-07 |
Family
ID=12387398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3346980A Granted JPS56131550A (en) | 1980-03-18 | 1980-03-18 | Separation of l-isoleucine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56131550A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0276526U (en) * | 1988-11-30 | 1990-06-12 | ||
| CN106831465A (en) * | 2016-12-28 | 2017-06-13 | 安徽省虹升生物股份有限公司 | A kind of method by hydrolyzing refinement beta Alanine in gelatine |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0617343B2 (en) * | 1986-04-28 | 1994-03-09 | 味の素株式会社 | Method for separating and purifying isoleucine |
| FR2603581B1 (en) * | 1986-04-28 | 1993-08-13 | Ajinomoto Kk | PROCESS FOR ISOLATING AND PURIFYING AMINO ACIDS BY CHROMATOGRAPHY |
-
1980
- 1980-03-18 JP JP3346980A patent/JPS56131550A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0276526U (en) * | 1988-11-30 | 1990-06-12 | ||
| CN106831465A (en) * | 2016-12-28 | 2017-06-13 | 安徽省虹升生物股份有限公司 | A kind of method by hydrolyzing refinement beta Alanine in gelatine |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56131550A (en) | 1981-10-15 |
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