JPH04360859A - Purification of tyrosine by hydrochloride crystallization method - Google Patents
Purification of tyrosine by hydrochloride crystallization methodInfo
- Publication number
- JPH04360859A JPH04360859A JP23367691A JP23367691A JPH04360859A JP H04360859 A JPH04360859 A JP H04360859A JP 23367691 A JP23367691 A JP 23367691A JP 23367691 A JP23367691 A JP 23367691A JP H04360859 A JPH04360859 A JP H04360859A
- Authority
- JP
- Japan
- Prior art keywords
- tyrosine
- crystals
- phenylalanine
- approximately
- hydrochloride
- 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
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 title claims abstract description 76
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 title claims abstract description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000002425 crystallisation Methods 0.000 title abstract description 30
- 238000000746 purification Methods 0.000 title description 5
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims abstract description 37
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000013078 crystal Substances 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000012535 impurity Substances 0.000 claims description 13
- 229960004441 tyrosine Drugs 0.000 abstract description 63
- 230000008025 crystallization Effects 0.000 abstract description 18
- 238000003756 stirring Methods 0.000 abstract description 12
- JJWFIVDAMOFNPS-QRPNPIFTSA-N (2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 JJWFIVDAMOFNPS-QRPNPIFTSA-N 0.000 abstract description 10
- 239000000356 contaminant Substances 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 229940024606 amino acid Drugs 0.000 abstract description 2
- 150000001413 amino acids Chemical class 0.000 abstract description 2
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 238000001802 infusion Methods 0.000 abstract description 2
- 239000008187 granular material Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229960005190 phenylalanine Drugs 0.000 description 30
- 239000000243 solution Substances 0.000 description 14
- 238000006386 neutralization reaction Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、医薬用アミノ酸輸液、
化粧品等に有用なＬ−チロシン（ｐ−オキシフェニルア
ラニン）の工業的かつ経済的な精製法であり、特にフェ
ニルアラニンを主とする夾雑物を淘汰する精製方法に関
する。[Industrial Application Field] The present invention relates to pharmaceutical amino acid infusions,
This is an industrial and economical purification method for L-tyrosine (p-oxyphenylalanine) useful for cosmetics, etc., and particularly relates to a purification method for eliminating impurities mainly containing phenylalanine.
【０００２】0002
【従来の技術】従来、Ｌ−チロシンの晶析による精製法
としては、チロシン溶液のｐＨを９〜１２に調整した後
、クエン酸等の不要物を分離し得られた水溶液のｐＨを
６〜８にすることによってチロシンのフリー体として晶
析させる方法（以下、中和晶析法という）がとられてい
た（特公昭６０−６１５５３号公報参照）。[Prior Art] Conventionally, in the purification method of L-tyrosine by crystallization, the pH of a tyrosine solution was adjusted to 9 to 12, and then unnecessary substances such as citric acid were separated, and the pH of the resulting aqueous solution was adjusted to 6 to 12. 8 to crystallize tyrosine as a free form (hereinafter referred to as neutralization crystallization method) (see Japanese Patent Publication No. 60-61553).
【０００３】通常、中和晶析法によるチロシンのフリー
体の精製方法においても、夾雑物として存在するフェニ
ルアラニンが淘汰できることは認められているが、化学
構造の類似に起因して物性も類似していることからチロ
シンとフェニルアラニンの分離は容易ではなく、医薬用
原料として要求されるグレードまでフェニルアラニンを
主とする夾雑物を淘汰し高純度のチロシンを取得するた
めには、中和晶析を繰り返す必要があった。[0003] Although it is generally recognized that phenylalanine present as a contaminant can be removed in the method of purifying the free form of tyrosine by neutralization crystallization method, the physical properties are also similar due to the similarity of the chemical structure. Therefore, it is not easy to separate tyrosine and phenylalanine, and it is necessary to repeat neutralization crystallization in order to eliminate impurities, mainly phenylalanine, and obtain highly pure tyrosine to the grade required as a pharmaceutical raw material. was there.
【０００４】更に、中和晶析により生成したＬ−チロシ
ンのフリー体結晶は非常に微細であるため、通常使用さ
れる遠心分離型のバスケットセパレーターでは脱水性が
悪く、その為、腐敗すなわち微生物によるチロシン分解
を引き起こし易かった。これを防止するため分離した該
結晶を乾燥するか、または低温で保存しておく必要があ
った。Furthermore, since the free crystals of L-tyrosine produced by neutralization crystallization are very fine, the centrifugal type basket separator that is commonly used has poor dehydration properties, resulting in decomposition, which is caused by microorganisms. It was easy to cause tyrosine degradation. To prevent this, it was necessary to dry the separated crystals or store them at low temperatures.
【０００５】[0005]
【発明が解決しようとする課題】本発明が解決しようと
する課題は、チロシン晶析率（収率）を維持し高純度チ
ロシンを得るために、主にフェニルアラニンを効率的に
除去できるチロシンの晶析方法を探索することにある。Problems to be Solved by the Invention The problems to be solved by the present invention are to obtain tyrosine crystals that can effectively remove phenylalanine, in order to maintain the tyrosine crystallization rate (yield) and obtain high-purity tyrosine. The goal is to explore analytical methods.
【０００６】[0006]
【課題を解決するための手段】本発明者は、フェニルア
ラニンを含む夾雑物を含有するチロシン溶液からチロシ
ンを精製するに際し、チロシンを塩酸塩結晶の形で晶析
せしめ該結晶を分離することにより、晶析率（晶析率７
０％以上）の相違に関わらず、フェニルアラニンを含む
夾雑物を効率的に淘汰できることを見いだし、本発明を
完成させるに至った。本発明の精製方法を以下、塩酸塩
晶析法という。[Means for Solving the Problems] The present inventor has solved the problem by crystallizing tyrosine in the form of hydrochloride crystals and separating the crystals when purifying tyrosine from a tyrosine solution containing impurities including phenylalanine. Crystallization rate (crystallization rate 7
The present inventors have discovered that impurities containing phenylalanine can be efficiently removed regardless of the difference (0% or more), and have completed the present invention. The purification method of the present invention is hereinafter referred to as the hydrochloride crystallization method.
【０００７】以下に本発明を具体的に記述する。The present invention will be specifically described below.
【０００８】本発明で言うフェニルアラニンを含む夾雑
物とは、フェニルアラニン以外に、何を含んでいてもよ
い。例えば、その他の物質としてイソロイシン、アラニ
ン、ロイシン、シスチン等がある。（フェニルアラニン
）／（チロシン）重量比は、通常０．１−５％が良い。
また、フェニルアラニンを含む夾雑物を含有するチロシ
ン溶液は懸濁液であっても清澄液であってもよく、チロ
シン濃度は通常５．０−１０．０ｇ／ｄｌであるが特に
限定されない。[0008] The phenylalanine-containing impurities referred to in the present invention may contain anything other than phenylalanine. For example, other substances include isoleucine, alanine, leucine, cystine, etc. The (phenylalanine)/(tyrosine) weight ratio is usually preferably 0.1-5%. Further, the tyrosine solution containing impurities including phenylalanine may be a suspension or a clear liquid, and the tyrosine concentration is usually 5.0-10.0 g/dl, but is not particularly limited.
【０００９】フェニルアラニンを含む夾雑物を含有する
チロシン溶液（懸濁状態である）を加熱し、攪はんしな
がら塩酸を添加し、完全に溶解させる。添加する塩酸量
は、チロシンの１．０−１．５倍モル、好ましくは１．
３倍モル程度がよい。完全に溶解させる際、チロシンが
分解しない程度に加熱してもよい。加熱温度は、６０−
８０℃、好ましくは７０℃程度に制御するのがよい。得
られた溶解液は濃縮または塩酸の更なる添加によって、
溶解液中の塩酸濃度を上昇させ、チロシン塩酸塩結晶を
析出させる。その際、該溶解液中の塩酸濃度は塩酸塩の
溶解度の観点から１８−２５重量％、好ましくは２０重
量％程度まで上昇させるのがよい。その後、攪はんしな
がらゆっくり１０−０℃、好ましくは５℃まで冷却する
）。得られたスラリーは分離機、例えば遠心分離型のバ
スケットセパレーター等に付し、Ｌ−チロシン塩酸塩結
晶を取得することができる。該チロシン結晶の粒径は０
．５−０．３ｍｍであり、チロシン結晶（フリー体）の
粒径（０．１−０．０５ｍｍ）よりも大きいことから付
着水分量が少なくなり、チロシンを高晶析率かつ高純度
で得ることができる。例えば、原料の（フェニルアラニ
ン）／（チロシン）重量比が５％の場合、得られるチロ
シン塩酸塩のチロシン換算収率が８０％のとき（フェニ
ルアラニン）／（チロシン）重量比は ０．６２％で
、不純物淘汰性が非常によい。これにより、晶析段数が
削減でき、チロシンの生産性を高めることができる。
また、チロシン塩酸塩結晶はチロシン結晶（フリー体）
に比べ保存安定性に優れているので、室温での長期保存
も可能となる。[0009] A tyrosine solution (in a suspended state) containing impurities including phenylalanine is heated, and hydrochloric acid is added while stirring to completely dissolve the impurities. The amount of hydrochloric acid to be added is 1.0 to 1.5 times the mole of tyrosine, preferably 1.0 to 1.5 times the mole of tyrosine.
About 3 times the mole is good. When completely dissolving, heating may be performed to an extent that tyrosine is not decomposed. The heating temperature is 60-
The temperature is preferably controlled at about 80°C, preferably about 70°C. The resulting solution is concentrated or by further addition of hydrochloric acid.
The concentration of hydrochloric acid in the solution is increased to precipitate tyrosine hydrochloride crystals. At that time, the concentration of hydrochloric acid in the solution is preferably increased to 18-25% by weight, preferably about 20% by weight from the viewpoint of solubility of the hydrochloride. Then slowly cool to 10-0°C, preferably 5°C while stirring). The obtained slurry can be applied to a separator, such as a centrifugal basket separator, to obtain L-tyrosine hydrochloride crystals. The particle size of the tyrosine crystal is 0
．． 5-0.3 mm, which is larger than the particle size (0.1-0.05 mm) of tyrosine crystals (free body), so the amount of attached moisture is reduced, and tyrosine can be obtained with a high crystallization rate and high purity. Can be done. For example, when the (phenylalanine)/(tyrosine) weight ratio of the raw material is 5%, and the yield of the obtained tyrosine hydrochloride in terms of tyrosine is 80%, the (phenylalanine)/(tyrosine) weight ratio is 0.62%. Very good at eliminating impurities. Thereby, the number of crystallization stages can be reduced and the productivity of tyrosine can be increased. In addition, tyrosine hydrochloride crystals are tyrosine crystals (free form)
Since it has superior storage stability compared to , it can be stored for a long time at room temperature.
【００１０】（実験例）次に、フェニルアラニン淘汰性
に関して、塩酸塩晶析法と従来の中和晶析法について比
較する。(Experimental Example) Next, the hydrochloride crystallization method and the conventional neutralization crystallization method will be compared in terms of phenylalanine selection.
【００１１】始めに、従来の中和晶析法の実験例につい
て記載する。（フェニルアラニン）／（チロシン）重量
比 ５％のフェニルアラニンを含む夾雑物を含有する
チロシン溶液（チロシン７−１０ｇ／ｄｌ）３Ｌを加熱
し、攪はんしながら塩酸を添加し、完全に溶解させた。
完全溶解時のｐＨは１程度であり、加熱温度は、７０℃
程度とした。その溶解液に２７％水酸化ナトリウム水溶
液をゆっくり攪拌しつつ添加し中和し、チロシン結晶（
フリー体）を析出させた。なお、中和時のｐＨは３〜４
程度である。析出結晶を含むスラリーをゆっくり室温（
２０℃）まで空冷で冷却した。得られたスラリーを遠心
分離型のバスケットセパレーターＨ−１２２型（国産社
製）で３０００ｒｐｍ、約１０分かけて分離し、Ｌ−チ
ロシン結晶（フリー体）を得た。First, an experimental example of the conventional neutralization crystallization method will be described. (Phenylalanine)/(tyrosine) 3L of a tyrosine solution (tyrosine 7-10g/dl) containing impurities containing phenylalanine at a weight ratio of 5% was heated, and hydrochloric acid was added while stirring to completely dissolve it. . The pH at complete dissolution is approximately 1, and the heating temperature is 70°C.
It was set as the degree. A 27% aqueous sodium hydroxide solution was added to the solution while stirring slowly to neutralize it, and tyrosine crystals (
Free body) was precipitated. In addition, the pH during neutralization is 3 to 4.
That's about it. The slurry containing the precipitated crystals was slowly heated to room temperature (
The mixture was air-cooled to 20°C. The obtained slurry was separated using a centrifugal basket separator model H-122 (manufactured by Kokusan Co., Ltd.) at 3000 rpm for about 10 minutes to obtain L-tyrosine crystals (free form).
【００１２】次に塩酸塩晶析法の実験例について記載す
る。（フェニルアラニン）／（チロシン）重量比 ５
％のフェニルアラニンを含む夾雑物を含有するチロシン
溶液（チロシン７５−８０ｇ／ｄｌ）２００ｍｌを加熱
し、攪はんしながら塩酸を総チロシン量の１．３倍モル
程度添加し、７０℃程度で加熱して完全に溶解させた。
得られた溶解液に塩酸を２０重量％程度になるまで更に
添加した。その後、攪はんしながらゆっくり５℃まで冷
却した。得られたスラリーは遠心分離型のバスケットセ
パレーターＨ−１２２型（国産社製）で３０００ｒｐｍ
、１０分かけて分離し、Ｌ−チロシン塩酸塩結晶を取得
した。Next, an experimental example of the hydrochloride crystallization method will be described. (phenylalanine)/(tyrosine) weight ratio 5
Heat 200 ml of a tyrosine solution (tyrosine 75-80 g/dl) containing impurities including % phenylalanine, add about 1.3 times the mole of hydrochloric acid to the total amount of tyrosine while stirring, and heat at about 70°C. and completely dissolved. Hydrochloric acid was further added to the obtained solution until the concentration was about 20% by weight. Thereafter, the mixture was slowly cooled to 5°C while stirring. The obtained slurry was centrifuged at 3000 rpm using a centrifugal basket separator model H-122 (manufactured by Kokusan Co., Ltd.).
, and was separated for 10 minutes to obtain L-tyrosine hydrochloride crystals.
【００１３】上記実験結果に基づき、塩酸塩晶析法及び
中和晶析法の晶析率とフェニルアラニン淘汰率（Ｐ／Ｔ
淘汰率）の関係を図１に示す。図１中のＰ／Ｔ淘汰率と
は、１回の晶析におけるチロシン量に対するフェニルア
ラニン含量の淘汰する割合、即ち［（フェニルアラニン
）／（チロシン）］×１００（％）を意味する。塩酸塩
晶析法も中和晶析法も晶析率が上昇するにつれて、フェ
ニルアラニンの淘汰性が上昇する。しかしながら、本発
明の塩酸塩晶析法はフェニルアラニンの淘汰性について
広い晶析率範囲にわたり従来法の中和晶析法と比べて優
れている。Based on the above experimental results, the crystallization rate and phenylalanine selection rate (P/T
Figure 1 shows the relationship between the culling rate and the culling rate. The P/T selection rate in FIG. 1 means the selection ratio of the phenylalanine content to the tyrosine amount in one crystallization, that is, [(phenylalanine)/(tyrosine)]×100 (%). In both the hydrochloride crystallization method and the neutralization crystallization method, as the crystallization rate increases, the selectivity of phenylalanine increases. However, the hydrochloride crystallization method of the present invention is superior to the conventional neutralization crystallization method in terms of selection of phenylalanine over a wide crystallization rate range.
【００１４】以下、本発明を実施例により詳細に説明す
る。[0014] The present invention will now be explained in detail by way of examples.
実施例１
Ｌ−チロシン結晶２５０ｇとＬ−フェニルアラニン結晶
１２．５ｇ（対チロシン５％）を２Ｌのビーカーに採り
、これに純水（２５℃）１５０ｇと３５％塩酸（２５℃
）１８０ｇ（対チロシン：１．３倍モル）を添加し、メ
カニカルスターラーでよく攪はんし懸濁させた。この懸
濁液を攪はんさせながら７０℃に加熱し完全溶解させた
。攪はんしながら溶解液を５０℃まで自然空冷したとこ
ろで３５％塩酸１４０ｇをゆっくり添加していくと次第
にチロシン塩酸塩が析出して懸濁液になる。この懸濁液
を５℃までゆっくり冷却した。析出した塩酸塩結晶を含
むスラリーを小型遠心分離機にかけてＬ−チロシン塩酸
塩２４０ｇ（チロシン換算：２００ｇ）を得た。（チロ
シン晶析率：８０％、フェニルアラニン含量：０．４５
％、フェニルアラニン淘汰率：８８％、粒径：０．５−
０．３ｍｍ、付着水分：１２％）Example 1 250 g of L-tyrosine crystals and 12.5 g of L-phenylalanine crystals (5% to tyrosine) were placed in a 2 L beaker, and 150 g of pure water (25°C) and 35% hydrochloric acid (25%
) 180 g (1.3 times the mole of tyrosine) was added thereto, and the mixture was thoroughly stirred with a mechanical stirrer to suspend it. This suspension was heated to 70° C. while stirring to completely dissolve it. While stirring, the solution was naturally air-cooled to 50° C., and 140 g of 35% hydrochloric acid was slowly added thereto, and tyrosine hydrochloride was gradually precipitated to form a suspension. This suspension was slowly cooled to 5°C. The slurry containing the precipitated hydrochloride crystals was passed through a small centrifuge to obtain 240 g of L-tyrosine hydrochloride (200 g in terms of tyrosine). (Tyrosine crystallization rate: 80%, phenylalanine content: 0.45
%, Phenylalanine selection rate: 88%, Particle size: 0.5-
0.3mm, attached moisture: 12%)
【００１５】実施例２
Ｌ−チロシン結晶２５０ｇとＬ−フェニルアラニン結晶
１２．５ｇ（対チロシン５％）を５Ｌのビーカーに採り
、これに純水（２５℃）２．９Ｌと３５％塩酸（２５℃
）１８０ｇ（対チロシン：１．３倍モル）を添加しメカ
ニカルスターラーでよく攪はんし懸濁させた。この懸濁
液を攪はんさせながら７０℃に加熱し完全溶解させた。
攪はんしながら溶解液に２７％苛性ソーダ３３５ｇをゆ
っくり添加していくと次第にチロシン結晶が析出して懸
濁液になる。この懸濁液をゆっくり冷却した。得られた
スラリーを小型遠心分離機にかけてＬ−チロシン２５１
ｇを得た。（チロシン晶析率：９８％、フェニルアラニ
ン含量：１．９３％、フェニルアラニン淘汰率：６０％
、粒径：０．１−０．０５ｍｍ、付着水分：２２％）Example 2 250g of L-tyrosine crystals and 12.5g of L-phenylalanine crystals (5% to tyrosine) were placed in a 5L beaker, and 2.9L of pure water (25°C) and 35% hydrochloric acid (25%
) 180 g (1.3 times the mole of tyrosine) was added and stirred well with a mechanical stirrer to suspend. This suspension was heated to 70° C. while stirring to completely dissolve it. When 335 g of 27% caustic soda was slowly added to the solution while stirring, tyrosine crystals were gradually precipitated to form a suspension. This suspension was slowly cooled. The resulting slurry was passed through a small centrifuge to extract L-tyrosine 251.
I got g. (Tyrosine crystallization rate: 98%, phenylalanine content: 1.93%, phenylalanine selection rate: 60%
, particle size: 0.1-0.05mm, attached moisture: 22%)
【００１６】[0016]
【発明の効果】本発明によれば、従来より粒径が大きく
付着水分が少ないチロシンを高晶析率かつ高純度で得る
ことができることから、晶析回数を減らすことができ、
チロシンの生産性を高めることができる。また、チロシ
ン塩酸塩結晶はチロシン結晶（フリー体）に比べ保存安
定性に優れているので、室温での長期保存も可能となる
。[Effects of the Invention] According to the present invention, tyrosine having a larger particle size and less adhering moisture than before can be obtained with a high crystallization rate and high purity, so the number of crystallizations can be reduced.
Tyrosine productivity can be increased. Furthermore, since tyrosine hydrochloride crystals have better storage stability than tyrosine crystals (free form), long-term storage at room temperature is possible.
Claims (1)
するチロシン溶液からチロシンを精製するに際し、チロ
シンを塩酸塩結晶の形で晶析せしめ該結晶を分離するこ
とにより、フェニルアラニンを含む夾雑物を淘汰するこ
とを特徴とするチロシンの精製方法。Claim 1: When purifying tyrosine from a tyrosine solution containing impurities including phenylalanine, the impurities containing phenylalanine are removed by crystallizing tyrosine in the form of hydrochloride crystals and separating the crystals. A method for purifying tyrosine, characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23367691A JPH04360859A (en) | 1991-06-07 | 1991-06-07 | Purification of tyrosine by hydrochloride crystallization method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23367691A JPH04360859A (en) | 1991-06-07 | 1991-06-07 | Purification of tyrosine by hydrochloride crystallization method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04360859A true JPH04360859A (en) | 1992-12-14 |
Family
ID=16958792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23367691A Pending JPH04360859A (en) | 1991-06-07 | 1991-06-07 | Purification of tyrosine by hydrochloride crystallization method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04360859A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114560783A (en) * | 2022-02-22 | 2022-05-31 | 福建科宏生物工程股份有限公司 | Method for extracting L-tyrosine from conversion solution |
-
1991
- 1991-06-07 JP JP23367691A patent/JPH04360859A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114560783A (en) * | 2022-02-22 | 2022-05-31 | 福建科宏生物工程股份有限公司 | Method for extracting L-tyrosine from conversion solution |
| CN114560783B (en) * | 2022-02-22 | 2024-04-30 | 福建科宏生物工程股份有限公司 | Extraction method of L-tyrosine in conversion solution |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0331258A (en) | Purification of tryptophan | |
| JP4560155B2 (en) | Purification and crystallization method of riboflavin | |
| JP3617091B2 (en) | Purification method of basic amino acids | |
| JPH04360859A (en) | Purification of tyrosine by hydrochloride crystallization method | |
| JPH03504320A (en) | Subtilisin crystallization method | |
| JPH07285919A (en) | Production of l-aspartic acid from ammonium aspartate | |
| US2325339A (en) | Purification of caustic | |
| JPS60217897A (en) | Method for separating and purifying lactic acid | |
| US4551548A (en) | Process for the recovery of S-(carboxymethyl)-(R)-cysteine and S-(carboxymethyl)-(S)-cysteine | |
| JPS604168A (en) | Crystallization of tryptophan | |
| JPS604155A (en) | Separation of l-leucine and l-isoleucine | |
| JPH0352455B2 (en) | ||
| JP3541440B2 (en) | Crystallization method of L-cystine and novel crystal | |
| KR950006893B1 (en) | Novel aspartic acid crystals and a process for the production thereof | |
| JPS6072857A (en) | Production of high-purity s-carboxymethyl-l-cysteine hydrochloride | |
| JPS60184054A (en) | Method for purifying optically active lysine | |
| JPH0342268B2 (en) | ||
| JPH0820572A (en) | Method for separating taurine | |
| JPS626702B2 (en) | ||
| JPS63233958A (en) | Purification of aspartic acid | |
| JPH0512344B2 (en) | ||
| JPH0456814B2 (en) | ||
| JPH0336824B2 (en) | ||
| JPH05178801A (en) | Method for crystallizing l-phenylalanine | |
| JPH0443062B2 (en) |