JPH05153988A - Method for isolating tryptophan - Google Patents
Method for isolating tryptophanInfo
- Publication number
- JPH05153988A JPH05153988A JP32051191A JP32051191A JPH05153988A JP H05153988 A JPH05153988 A JP H05153988A JP 32051191 A JP32051191 A JP 32051191A JP 32051191 A JP32051191 A JP 32051191A JP H05153988 A JPH05153988 A JP H05153988A
- Authority
- JP
- Japan
- Prior art keywords
- tryptophan
- concentration
- aqueous solution
- crystals
- state
- 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.)
- Granted
Links
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、トリプトファンを含む
水溶液からの同物質の単離法に関するものである。FIELD OF THE INVENTION The present invention relates to a method for isolating tryptophan from an aqueous solution containing the same.
【０００２】なお、本発明は、一般的には、Ｌ−トリプ
トファンの単離法を想定するものであるが、Ｄ−あるい
はＤＬ−トリプトファンにも適用することは、十分可能
である。The present invention generally envisages a method for isolating L-tryptophan, but it is sufficiently applicable to D- or DL-tryptophan.
【０００３】[0003]
【従来の技術および発明が解決しようとする課題】トリ
プトファンはアミノ酸の一種であり、特にＬ体は人間の
みならず生物全般の代謝過程に重要な役割を果たしてい
る。このため、医薬業・食品業・飼料業・農業などの産
業にとって、非常に利用価値の高い物質である。2. Description of the Related Art Tryptophan is a kind of amino acid, and especially L-form plays an important role not only in humans but also in metabolic processes in all organisms. Therefore, it is an extremely valuable substance for industries such as the pharmaceutical industry, food industry, feed industry, and agriculture.
【０００４】トリプトファンの製造法に関しては、多種
多様な製造法が広く知られている。そして、製造から単
離の過程では、トリプトファンは水溶液として存在して
いるのが一般的であり、このため、水溶液中からの同物
質の単離方法に関しても種々の技術が提示されている。A wide variety of methods for producing tryptophan are widely known. In the process of production and isolation, tryptophan generally exists as an aqueous solution. Therefore, various techniques have been proposed for the method of isolating the same from the aqueous solution.
【０００５】この範中の技術の代表例の一つとして、ト
リプトファンを含む水溶液を濃縮し、その後、冷却によ
りトリプトファンの結晶を析出させる方法を挙げること
ができるが、濃縮時に析出するトリプトファンの結晶が
引き起こす発泡・突沸現象に注意を要することが従来よ
りよく知られている。As a typical example of the technique in this range, there can be mentioned a method of concentrating an aqueous solution containing tryptophan and then precipitating tryptophan crystals by cooling. It is well known in the past that attention must be paid to the foaming and bumping phenomena that occur.
【０００６】すなわち、トリプトファンを含む水溶液を
常圧または減圧下で濃縮させると、トリプトファン濃度
がその水溶液での飽和溶解度を上回った時点より、濃縮
液中にはトリプトファンの結晶が析出し始める。過飽和
状態で濃縮操作を継続するにつれて、析出した結晶が、
結晶表面の疎水性のために水溶液表面に浮き始め、泡を
巻き込むために発泡または突沸が起こるのである。ま
た、結晶が水溶液表面を覆うことで、濃縮自体も進行し
にくくなる。That is, when an aqueous solution containing tryptophan is concentrated under normal pressure or reduced pressure, crystals of tryptophan start to precipitate in the concentrated solution when the concentration of tryptophan exceeds the saturated solubility in the aqueous solution. As the concentration operation was continued in a supersaturated state, the precipitated crystals were
Due to the hydrophobicity of the crystal surface, it begins to float on the surface of the aqueous solution, and foaming or bumping occurs due to the inclusion of bubbles. In addition, the crystals themselves cover the surface of the aqueous solution, which makes it difficult for the concentration itself to proceed.
【０００７】これに対して、主に界面活性剤を濃縮時に
添加する等の改善策が既に開示されている（ＷＯ−９０
−０９３７２）。しかし、この方法では、必ずしも発泡
・突沸を完全に防止することはできない。On the other hand, improvement measures such as mainly adding a surfactant at the time of concentration have already been disclosed (WO-90).
-09372). However, this method cannot always completely prevent foaming and bumping.
【０００８】例えば、発酵法または酵素法により製造し
たＬ−トリプトファンを分離・精製するに際して、溶液
中の菌体成分等を活性炭に吸着させて除去したトリプト
ファン溶液を用いた場合、濃縮液のトリプトファン濃度
が約８重量％を越えた時点より発泡・突沸が観察され
る。さらに濃縮を続けると、添加した界面活性剤等の濃
度にもよるが、約１０重量％を越えた時点で界面活性剤
等を添加した効果を次第に見いだせなくなり、約１３重
量％以上では全く効果を期待できない。For example, in the case of separating and purifying L-tryptophan produced by a fermentation method or an enzyme method, when a tryptophan solution obtained by adsorbing and removing cell components in the solution by adsorbing on activated carbon is used, the concentration of tryptophan in the concentrate is Foaming and bumping are observed from the time when the content exceeds about 8% by weight. When the concentration is further continued, the effect of adding the surfactant etc. cannot be gradually found when the concentration exceeds about 10% by weight, depending on the concentration of the added surfactant, etc. I can't expect.
【０００９】また、トリプトファンの濃縮度が上昇する
につれて、濃縮液の粘度が高くなるため、濃縮液の濾過
性もこれに応じて悪化し、引いては、析出したトリプト
ファンの結晶を効率よく分離することが困難となる。Further, as the concentration of tryptophan increases, the viscosity of the concentrate increases, so that the filterability of the concentrate also deteriorates accordingly, and the precipitated crystals of tryptophan are efficiently separated. Becomes difficult.
【００１０】このため、約１３重量％以上にトリプトフ
ァンを濃縮させるプロセスは、工業的には成立しにく
く、それ故に収率向上の妨げとなっている。Therefore, the process of concentrating tryptophan to about 13% by weight or more is not industrially feasible and therefore hinders improvement in yield.
【００１１】[0011]
【課題を解決するための手段】そこで、本発明者らは、
上記の問題点を克服し、トリプトファンを含む水溶液か
ら高収率でトリプトファンを単離するプロセスについて
検討を行い、濃縮時に析出するトリプトファンの結晶
を、析出と同時に取り除くことで、発泡または突沸を防
止しつつ結晶を分離することができる事を見いだし、本
発明を完成させた。Therefore, the present inventors have
To overcome the above problems, we investigated the process of isolating tryptophan from an aqueous solution containing tryptophan in high yield, and remove the tryptophan crystals that precipitate during concentration, simultaneously with the precipitation to prevent foaming or bumping. While discovering that crystals can be separated, the present invention has been completed.
【００１２】即ち、本発明は、トリプトファンを含む水
溶液からトリプトファンの結晶を晶出させるに際して、
常圧または減圧下で濃縮を行い、トリプトファン濃度が
その水溶液での飽和溶解度を上回った状態で結晶化を起
こさせた後、発泡または突沸が起こっていない状態でそ
の溶液の全部または一部を取り出して、濃縮時の温度を
下回らないように保持したままでトリプトファンの結晶
を濃縮液から分離し、続いてその濾液を再び濃縮液に供
給することにより、連続的または段続的に濃縮操作を継
続することを特徴とするトリプトファンの単離法であ
る。That is, according to the present invention, when crystallizing tryptophan crystals from an aqueous solution containing tryptophan,
After concentration under normal pressure or reduced pressure and crystallization when the tryptophan concentration exceeds the saturated solubility in the aqueous solution, take out all or part of the solution without foaming or bumping. , The tryptophan crystals are separated from the concentrate while keeping the temperature at the time of concentration not to fall, and then the filtrate is supplied to the concentrate again to continue the concentration operation continuously or continuously. And a method for isolating tryptophan.
【００１３】本発明方法のトリプトファンを含む水溶液
の濃縮過程において、トリプトファン結晶が析出してい
るものの、発泡または突沸が全く起こっていない状態、
即ち、飽和状態を上回った状態を、今仮に“状態Ａ”と
呼ぶことにする。In the process of concentrating the aqueous solution containing tryptophan of the method of the present invention, a state in which tryptophan crystals are precipitated but no foaming or bumping occurs at all,
That is, the state in which the saturated state is exceeded is now temporarily called "state A".
【００１４】“状態Ａ”は、ある一定の濃度範囲のトリ
プトファン水溶液を指している。その具体的な濃度範囲
は、イオン強度・ｐＨ・温度・不純物の有無等のトリプ
トファンを含む水溶液の組成・性状によって異なってく
るが、より一般的には、約２重量％から１０重量％の間
である。"State A" refers to an aqueous solution of tryptophan within a certain concentration range. The specific concentration range varies depending on the composition and properties of the aqueous solution containing tryptophan, such as ionic strength, pH, temperature, and the presence or absence of impurities, but more generally, it is between about 2% by weight and 10% by weight. Is.
【００１５】例えば、１００℃の単なるトリプトファン
水溶液の場合、この“状態Ａ”に相当するトリプトファ
ンの濃度範囲は、約４．８重量％から約９重量％の間で
ある。一方、７０℃の単なるトリプトファン水溶液の場
合、この“状態Ａ”に相当するトリプトファンの濃度範
囲は、約２．５重量％から約１１重量％の間である。ま
た、酵素法または発酵法によりトリプトファンを生じさ
せ、活性炭処理により菌体成分を除去した溶液（実施例
１参照）の場合、１００℃では、この“状態Ａ”に相当
するトリプトファンの濃度範囲は、約５重量％から約８
重量％の間である。For example, in the case of a simple tryptophan aqueous solution at 100 ° C., the concentration range of tryptophan corresponding to this “state A” is between about 4.8% by weight and about 9% by weight. On the other hand, in the case of a simple tryptophan aqueous solution at 70 ° C., the concentration range of tryptophan corresponding to this “state A” is between about 2.5 wt% and about 11 wt%. Further, in the case of a solution in which tryptophan is produced by an enzymatic method or a fermentation method and bacterial cell components are removed by activated carbon treatment (see Example 1), at 100 ° C., the concentration range of tryptophan corresponding to this “state A” is About 5% by weight to about 8
Between% by weight.
【００１６】トリプトファン水溶液の濃縮は常圧または
減圧いずれの条件でもよい。“状態Ａ”を濃縮過程で保
つための温度は、常温以上であれば特に制約はないが、
濃縮効率等を考慮した場合、好ましくは、６０℃から１
００℃の範囲である。Concentration of the tryptophan aqueous solution may be performed under normal pressure or reduced pressure. The temperature for maintaining the “state A” in the concentration process is not particularly limited as long as it is room temperature or higher.
Considering the concentration efficiency, etc., preferably from 60 ℃ to 1
It is in the range of 00 ° C.
【００１７】“状態Ａ”では、トリプトファンは過飽和
であるので、析出した結晶を取り除いた後に、同じ条件
下で濃縮を継続すれば容易にトリプトファン結晶が析出
する。また、例えば温度の低下等の変化により、トリプ
トファンの溶解度が低下しても、結晶は析出する。In the "state A", tryptophan is supersaturated. Therefore, if the precipitated crystals are removed and the concentration is continued under the same conditions, tryptophan crystals are easily precipitated. Further, even if the solubility of tryptophan decreases due to changes such as a decrease in temperature, crystals are precipitated.
【００１８】ここで、この“状態Ａ”の濃縮液の一部ま
たは全部を取り出し、その温度が濃縮時の温度を下回ら
ないように保持したままで、濾過等の分離操作によりト
リプトファン結晶のみを濃縮液から分離する。その濾液
を濃縮時の温度に保ったままで、再び“状態Ａ”の濃縮
液に戻した場合、濃縮液はほぼ'状態Ａ'に保たれること
になるので、さらに濃縮操作を継続することができる。
この操作を段続的に繰り返すことによりトリプトファン
結晶を高収率で得ることができる。Here, a part or all of this "state A" concentrate is taken out, and the tryptophan crystals alone are concentrated by a separation operation such as filtration while keeping the temperature so that it does not fall below the temperature at the time of concentration. Separate from liquid. When the filtrate is returned to the "state A" concentrate while keeping the temperature at the time of concentration, the concentrate will be kept in "state A", so the concentration operation can be continued. it can.
By repeating this operation step by step, tryptophan crystals can be obtained in high yield.
【００１９】また、この濃縮・結晶分離・再濃縮の操作
を同時に進行させた場合においては、濃縮液の状態を常
に“状態Ａ”に保ったままで、トリプトファン結晶を連
続的、かつ、高収率で分離することが可能となる。In the case where the operations of concentration, crystal separation and reconcentration are carried out at the same time, the tryptophan crystals are continuously produced at a high yield while keeping the state of the concentrate at "state A". It becomes possible to separate with.
【００２０】さらに、トリプトファンの結晶を分離する
際に、結晶を“状態Ａ”と同程度の温度の適量の温水で
洗浄することで、結晶中の不純物を低減することができ
る。Furthermore, when separating the crystals of tryptophan, the impurities in the crystals can be reduced by washing the crystals with an appropriate amount of warm water at the same temperature as in "state A".
【００２１】一方、“状態Ａ”の濃縮液の粘度は十分低
いので濾過操作には問題がない。このため、本発明にお
けるトリプトファンの結晶を分離するには、任意の遠心
分離機またはベルト濾過機を用いることができる。On the other hand, since the viscosity of the "state A" concentrate is sufficiently low, there is no problem in the filtration operation. Therefore, any desired centrifugal separator or belt filter can be used to separate the tryptophan crystals in the present invention.
【００２２】[0022]
実施例１ 特開昭６１−７０９９３において既に開示されている方
法と同様にして、大腸菌を培養して生産された酵素トリ
プトファンシンターゼの存在下、水溶液中でインドール
とセリンを縮合させてＬ−トリプトファン１５重量％を
含む状態で反応を終了させ、さらに、反応溶液中のトル
エンを加熱・留去した。純水で反応液を希釈し、さらに
硫酸にてｐＨを４．０に調整した後、約６０℃に加熱し
てＬ−トリプトファンを完全に溶解させた。約９５℃に
昇温した後、活性炭をこの溶液に加え、かくはんを続け
ながら約１時間保持した。この後、濾過により活性炭お
よび活性炭に吸着した菌体成分を除去した。Example 1 L-tryptophan 15 was prepared by condensing indole and serine in an aqueous solution in the presence of the enzyme tryptophan synthase produced by culturing Escherichia coli in the same manner as the method already disclosed in JP-A-61-70993. The reaction was terminated in a state of containing wt%, and toluene in the reaction solution was further heated and distilled off. The reaction solution was diluted with pure water, and the pH was adjusted to 4.0 with sulfuric acid, and then heated to about 60 ° C. to completely dissolve L-tryptophan. After the temperature was raised to about 95 ° C., activated carbon was added to this solution, and the stirring was continued for about 1 hour. Then, the activated carbon and the bacterial cell components adsorbed on the activated carbon were removed by filtration.
【００２３】このようにして前処理を施した約３．５重
量％のＬ−トリプトファンを含む水溶液３３７０ｇ（Ｌ
−トリプトファン分約１１８．０ｇ）を用いて以下の操
作を行った。3370 g of an aqueous solution containing about 3.5% by weight of L-tryptophan thus pretreated.
The following operation was carried out using tryptophan content (about 118.0 g).
【００２４】この溶液について、Ｌ−トリプトファン濃
度が約７．３重量％になるまで常圧で濃縮した後、（濃
縮液は発泡または突沸は全く生じなかった）濃縮液の温
度を９５℃に保ったまま濾過を行い、晶析したＬ−トリ
プトファンの結晶約３８．２ｇ（乾燥重量）を得た。ま
た、トリプトファンの結晶を、その湿重量とほぼ同量の
熱水で洗浄した。この時の濾洗液のＬ−トリプトファン
濃度は、約５．２重量％であった。一方、この時の濾過
速度は、約３０００ｍｌ／分であった。This solution was concentrated under atmospheric pressure until the L-tryptophan concentration reached about 7.3% by weight, and then the temperature of the concentrate (the concentrate did not cause foaming or bumping) was kept at 95 ° C. Filtration was performed as it was to obtain about 38.2 g (dry weight) of crystallized L-tryptophan crystals. The tryptophan crystals were washed with hot water in an amount almost equal to the wet weight. At this time, the concentration of L-tryptophan in the filter wash liquid was about 5.2% by weight. On the other hand, the filtration rate at this time was about 3000 ml / min.
【００２５】そこで、この濾洗液を再び約７．３重量％
になるまで常圧で加熱・濃縮した後、同様に濾過操作を
行って、再びＬ−トリプトファンの結晶約２５．５ｇ
（乾燥重量）を得た。Then, this filter washing liquid is again added to about 7.3% by weight.
After heating and concentrating at atmospheric pressure until the temperature reaches, the same filtration operation is performed, and again about 25.5 g of L-tryptophan crystals.
(Dry weight) was obtained.
【００２６】再度、この濃縮／濾過／洗浄／再濃縮の操
作を継続し、合計で７回繰り返した。各ステップでの、
結晶重量・Ｌ−トリプトファン収率・純度について、表
１に示した。This concentration / filtration / washing / reconcentration operation was continued again, and was repeated 7 times in total. At each step,
The crystal weight, L-tryptophan yield, and purity are shown in Table 1.
【００２７】得られた結晶は、合計で１１１．５ｇ（乾
燥重量）であった。また、濃縮前後での総合収率は９
２．２％であり、総合純度は９７．６％であった。The crystals obtained totaled 111.5 g (dry weight). The total yield before and after concentration is 9
It was 2.2%, and the overall purity was 97.6%.
【００２８】実施例２ 実施例１と同じ前処理を施した約３．５重量％のＬ−ト
リプトファンを含む水溶液１０００ｇ（Ｌ−トリプトフ
ァン分約３５．０ｇ）を用いて以下の操作を行った。Example 2 The following operations were carried out using 1000 g of an aqueous solution containing about 3.5% by weight of L-tryptophan (L-tryptophan content of about 35.0 g) which had been subjected to the same pretreatment as in Example 1.
【００２９】この溶液について、Ｌ−トリプトファン濃
度が約６．７重量％になるまで常圧で濃縮を行った後、
（濃縮液は発泡または突沸は全く生じなかった）濃縮液
の温度を９５℃に保ったままで、６０ｍｌ／分の速度で
連続的にこれを抜き出し、続けて濾過を行って、晶析し
たＬ−トリプトファン結晶を同じく連続的に分離した。
また、得られた結晶は、５ｍｌ／分の速度で熱水をフィ
ードして洗浄した。濾洗液は、ほぼ同様の速度で濃縮液
に戻した。この様な循環操作を濃縮液が初発液量の約２
０分の１に減少するまで継続した。一方、この時の濾過
速度は、給液速度とほぼ同様であった。After concentrating this solution under atmospheric pressure until the L-tryptophan concentration reaches about 6.7% by weight,
(The concentrated solution did not cause foaming or bumping at all) While the temperature of the concentrated solution was kept at 95 ° C., it was continuously extracted at a rate of 60 ml / min, followed by filtration to crystallize L- Tryptophan crystals were likewise continuously separated.
The obtained crystals were washed by feeding hot water at a rate of 5 ml / min. The filter wash solution was returned to the concentrated solution at almost the same rate. With such circulation operation, the concentrated liquid is about 2 times the initial liquid amount.
It continued until it decreased to 1/0. On the other hand, the filtration rate at this time was almost the same as the liquid supply rate.
【００３０】得られた結晶は、３３．５ｇ（乾燥重量）
であった。濃縮前後でのＬ−トリプトファンの収率は９
２．８％であり、純度は９７．０％であった。The crystals obtained were 33.5 g (dry weight).
Met. The yield of L-tryptophan before and after concentration was 9
It was 2.8% and the purity was 97.0%.
【００３１】比較例１ 実施例１と同じ前処理を施した約３．５重量％のＬ−ト
リプトファンを含む水溶液３５７０ｇ（Ｌ−トリプトフ
ァン分約１２５．０ｇ）を用いて以下の操作を行った。Comparative Example 1 The following operations were carried out using 3570 g of an aqueous solution containing about 3.5% by weight of L-tryptophan (L-tryptophan content of about 125.0 g) which had been subjected to the same pretreatment as in Example 1.
【００３２】この溶液について、Ｌ−トリプトファン濃
度が約８重量％になるまで常圧下、９５℃で濃縮を行っ
た。ここで、濃縮を行うについては、濃縮液の表面積が
大きくなるようにした。そして、このトリプトファン濃
度で濃縮液が発泡し始めたので、界面活性剤（アデカノ
ール−ＬＧ１０９：旭電化）を０．１ｇ添加することに
より、さらに濃縮を続けた。この後、発泡が起こる度
に、同消泡剤を添加した。また、トリプトファン濃度
が、約１３重量％を越えた時点より、濃縮液に窒素ガス
をパージすることにより、さらに濃縮を進行させた。This solution was concentrated at 95 ° C. under normal pressure until the L-tryptophan concentration became about 8% by weight. Here, regarding the concentration, the surface area of the concentrated liquid was increased. Then, since the concentrated liquid began to foam at this tryptophan concentration, 0.1 g of a surfactant (Adecanol-LG109: Asahi Denka Co., Ltd.) was added to continue further concentration. After this, the same defoamer was added each time foaming occurred. Further, when the tryptophan concentration exceeded about 13% by weight, the concentrated liquid was purged with nitrogen gas to further promote the concentration.
【００３３】この様にして長時間濃縮を続けて、トリプ
トファン濃度が１７．２重量％になるまで濃縮を継続し
た後、濃縮液の温度を３０℃に保ち、１時間結晶を熟成
させた。In this way, the concentration was continued for a long time until the tryptophan concentration reached 17.2% by weight, and then the temperature of the concentrate was kept at 30 ° C. to ripen the crystals for 1 hour.
【００３４】この濃縮液について濾過を行い、Ｌ−トリ
プトファンの結晶を分離した。なお、この時の濾過速度
は、約５００ｍｌ／分であった。続いて、得られた結晶
を、その湿重量と同程度の純水（３０℃）で洗浄した。The concentrated liquid was filtered to separate L-tryptophan crystals. The filtration rate at this time was about 500 ml / min. Subsequently, the obtained crystal was washed with pure water (30 ° C.) having a wet weight equivalent to that of the crystal.
【００３５】得られた結晶は、１１３．１ｇ（乾燥重
量）であった。濃縮前後でのＬ−トリプトファンの収率
は８４．０％であり、純度は９３．９％であった。The crystals obtained were 113.1 g (dry weight). The yield of L-tryptophan before and after the concentration was 84.0%, and the purity was 93.9%.
【００３６】[0036]
【表１】 [Table 1]
【００３７】[0037]
【発明の効果】本発明により、水溶液中のトリプトファ
ンを常圧または減圧下で濃縮により分離するに際して、
界面活性剤などの消泡剤を用いることなく、発泡または
突沸を伴わずに、高収率で水溶液中からトリプトファン
の回収する方法を達成することができる。According to the present invention, when tryptophan in an aqueous solution is separated by concentration under normal pressure or reduced pressure,
It is possible to achieve a method of recovering tryptophan from an aqueous solution in a high yield without using foaming or bumping without using an antifoaming agent such as a surfactant.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 宮原 徹 福岡県大牟田市浅牟田町30 三井東圧化学 株式会社内 (72)発明者 福原 信裕 福岡県大牟田市浅牟田町30 三井東圧化学 株式会社内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Tohru Miyahara 30 Asamu-cho, Omuta-shi, Fukuoka Prefecture Mitsui Toatsu Chemical Co., Ltd. Within
Claims (1)
トファンの結晶を晶出させるに際し、（イ）常圧または
減圧下で濃縮を行い、（ロ）トリプトファン濃度がその
水溶液での飽和溶解度を上回った状態で結晶化を起こさ
せ、（ハ）その溶液の全部または一部を取り出し、
（ニ）濃縮時の温度を下回らないように保持したままで
トリプトファンの結晶を濃縮液から分離し、（ホ）続い
てその濾液を再び濃縮液に供給することにより、（ヘ）
連続的または段続的に濃縮操作を継続することを特徴と
するトリプトファンの単離法。1. Crystallization of tryptophan crystals from an aqueous solution containing tryptophan is carried out by concentrating under (a) normal pressure or reduced pressure, and (b) crystals in a state where the tryptophan concentration exceeds the saturated solubility in the aqueous solution. And (c) take out all or part of the solution,
(D) The crystals of tryptophan are separated from the concentrate while keeping the temperature at the time of concentration so that it does not fall below (e), and then the filtrate is supplied to the concentrate again.
A method for isolating tryptophan, which comprises continuing the concentration operation continuously or continuously.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3320511A JP3014194B2 (en) | 1991-12-04 | 1991-12-04 | Isolation of tryptophan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3320511A JP3014194B2 (en) | 1991-12-04 | 1991-12-04 | Isolation of tryptophan |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05153988A true JPH05153988A (en) | 1993-06-22 |
| JP3014194B2 JP3014194B2 (en) | 2000-02-28 |
Family
ID=18122266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3320511A Expired - Fee Related JP3014194B2 (en) | 1991-12-04 | 1991-12-04 | Isolation of tryptophan |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3014194B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6284897B2 (en) * | 2000-01-13 | 2001-09-04 | Ajinomoto Co., Inc. | Method for crystallizing tryptophan |
| CN116283711A (en) * | 2023-02-21 | 2023-06-23 | 黑龙江新和成生物科技有限公司 | Preparation method of high-purity cake-shaped L-tryptophan crystal and product thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101572134B1 (en) * | 2014-01-29 | 2015-11-26 | 한국과학기술원 | Anti-slip pad usable in various conditions with easy usability |
-
1991
- 1991-12-04 JP JP3320511A patent/JP3014194B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6284897B2 (en) * | 2000-01-13 | 2001-09-04 | Ajinomoto Co., Inc. | Method for crystallizing tryptophan |
| CN116283711A (en) * | 2023-02-21 | 2023-06-23 | 黑龙江新和成生物科技有限公司 | Preparation method of high-purity cake-shaped L-tryptophan crystal and product thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3014194B2 (en) | 2000-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110776543B (en) | Adenosine primary mother liquor recovery method | |
| HU202282B (en) | Process for separating 2-keto-l-gulonic acid from fermentation juice | |
| JP3273578B2 (en) | Method for producing salt of ornithine with acidic amino acids or keto acids | |
| RU2616002C2 (en) | Method for cleaning 1,4-diaminobutane, cleaned by the provided method of 1,4-diaminobutane and polyamide obtained from it | |
| CN112679560A (en) | Kasugamycin crystallization process | |
| JP4482336B2 (en) | Method for producing isomaltulose crystals and reduced isomaltulose | |
| JP3014194B2 (en) | Isolation of tryptophan | |
| JP5996650B2 (en) | Method for separating and purifying 1,4-diaminobutane from fermentation broth | |
| KR100864673B1 (en) | Method of recovering L-Threonine from L-Threonine fermentation broth using a nonsolvent | |
| JP2646343B2 (en) | Method for producing L-aspartic acid from ammonium aspartate | |
| JP4361641B2 (en) | Separation and recovery method of optically active amino acid and optically active amino acid amide | |
| JPH03216195A (en) | Purification of amino acid-nucleic acid and derivative thereof | |
| JPS60169451A (en) | Separation and purification of l-phenylalanine | |
| JPS60217897A (en) | Method for separating and purifying lactic acid | |
| US1989093A (en) | Amino alcohols and the production thereof | |
| CN115626882B (en) | Purification method of creatine monohydrate | |
| JP3239452B2 (en) | Method for producing α-L-aspartyl-L-phenylalanine methyl ester hydrochloride | |
| CN115636772B (en) | Preparation method of high-purity creatine monohydrate | |
| US5329014A (en) | Method for recovering optically active tryptophan | |
| JPS604168A (en) | Crystallization of tryptophan | |
| JPH01102033A (en) | Removal of organic acid | |
| JP3270558B2 (en) | Purification method and production method of L-phenylalanine | |
| JPH05178801A (en) | Method for crystallizing l-phenylalanine | |
| JP2942380B2 (en) | Method for purifying methacrylamide | |
| JPH07238063A (en) | Method for recovering and purifying 5-aminolevulinic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |