JPS5939B2 - Production method of high purity adenosine triphosphate - Google Patents
Production method of high purity adenosine triphosphateInfo
- Publication number
- JPS5939B2 JPS5939B2 JP8027276A JP8027276A JPS5939B2 JP S5939 B2 JPS5939 B2 JP S5939B2 JP 8027276 A JP8027276 A JP 8027276A JP 8027276 A JP8027276 A JP 8027276A JP S5939 B2 JPS5939 B2 JP S5939B2
- Authority
- JP
- Japan
- Prior art keywords
- atp
- production
- fermentation
- high purity
- production method
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 title description 18
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 title description 2
- 238000000855 fermentation Methods 0.000 claims description 13
- 230000004151 fermentation Effects 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 claims description 3
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 6
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 6
- 230000002407 ATP formation Effects 0.000 description 5
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 4
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 3
- 229960005305 adenosine Drugs 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- WWMWAMFHUSTZTA-UHFFFAOYSA-N Adenosine tetraphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O WWMWAMFHUSTZTA-UHFFFAOYSA-N 0.000 description 1
- UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- WWMWAMFHUSTZTA-KQYNXXCUSA-N adenosine 5'-(pentahydrogen tetraphosphate) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O WWMWAMFHUSTZTA-KQYNXXCUSA-N 0.000 description 1
- LNQVTSROQXJCDD-UHFFFAOYSA-N adenosine monophosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(CO)C(OP(O)(O)=O)C1O LNQVTSROQXJCDD-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229940013361 cresol Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008103 glucose Substances 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
- 229960001867 guaiacol Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 235000020007 pale lager Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- -1 phosphoric acid compound Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Description
【発明の詳細な説明】
本発明は高純度アデノシントリリン酸（以下ＡＴＰと称
す）の製法に門する。DETAILED DESCRIPTION OF THE INVENTION The present invention is directed to a method for producing high purity adenosine triphosphate (hereinafter referred to as ATP).
ＡＴＰは生体内にさる高エネルギーリン酸化合物の一種
であり、その体内における役割は、直接エネルギー出納
に関するのみでなく、各種の補酵素を介して炭水化物、
蛋白質、脂肪代謝等に重大な作用を有し、医薬品として
、また、生化学研究用試薬として重要である。ATP is a type of high-energy phosphoric acid compound in the body, and its role in the body is not only related to direct energy balance, but also to carbohydrates and carbohydrates through various coenzymes.
It has important effects on protein and fat metabolism, and is important as a medicine and as a reagent for biochemical research.
ＡＴＰの製造法としては、直接筋肉から単離精製する方
法、有機化学的合成法および醗酵法などがあるが、工業
的に大量に生産する方法としては。Methods for producing ATP include direct isolation and purification from muscle, organic chemical synthesis, and fermentation, but these methods are not suitable for industrial mass production.
アデノシンを酵母により酵素的にリン酸化してＡＴＰｋ
得る方法が広く使用されている。Adenosine is enzymatically phosphorylated by yeast to produce ATPk.
methods are widely used.
酵母によるＡＴＰの製造法は、燐酸緩衝液に酵母、アデ
ノシン、糖類等を加え適温で反応させ。To produce ATP using yeast, yeast, adenosine, sugars, etc. are added to a phosphate buffer solution and reacted at an appropriate temperature.
その進行中にＡＴＰの生成率を測定し、その最大生成時
において酵母を濾別し、その濾液を適当に処理しＡＴＰ
ｋ取得するものであるがこの醗酵法によるＡＴＰ製造に
おける欠陥は副反応の生起に起因するＡＴＰの純度低下
にある。During the process, the production rate of ATP is measured, the yeast is filtered out at the time of maximum production, and the filtrate is appropriately treated to produce ATP.
However, the defect in ATP production by this fermentation method is that the purity of ATP is reduced due to the occurrence of side reactions.
即ち、この方法においてＡＴＰの生成が最高に達した時
点で即亥泪的とするＡＴＰだけを反応液より単離するこ
とが容易であれば問題ないが工業的に大量のＡＴＰ金生
産する場合、酵素の濾別管、後処理工程が繁雑なため後
処理工程での副反応の生起はさけがたく、このためＡＴ
Ｐの収率の低減のみならず品質の低下はさけがたいもの
であった。That is, in this method, there is no problem if it is easy to isolate only the ATP that is immediately activated from the reaction solution when the production of ATP reaches its maximum, but when producing ATP gold in large quantities industrially, Since the enzyme filtration tube and post-treatment process are complicated, side reactions are unavoidable in the post-treatment process, and therefore AT
Not only a decrease in the yield of P but also a decrease in quality was unavoidable.
即ち１本酵素反応におけるＡＴＰの生成機構全醗酵液中
のＡＴＰ関連化合物全経済的に測定する事により研究し
た結果、ＡＴＰの生成率が最大に達した後、ＡＴＰの一
部は、さらに酵素反応でリン酸化され、アデノシンテト
ラリン酸（以下ＡＴＴＰと称す）になり、また、一部は
酵素分解によりアデノシンジリン酸（以下ＡＤＰと称す
）およびアデノシンモノリン酸（以下ＡＭＰと称す）に
なりＡＴＰの生成率及び純度は低下する事及びＡＴＴＰ
の生起が後処理工程において最も除去しがたいものであ
る事を解明した。In other words, the production mechanism of ATP in a single enzyme reaction was studied by economically measuring ATP-related compounds in the entire fermentation solution. It is phosphorylated to become adenosine tetraphosphate (hereinafter referred to as ATTP), and some of it becomes adenosine diphosphate (hereinafter referred to as ADP) and adenosine monophosphate (hereinafter referred to as AMP) through enzymatic decomposition, increasing the production rate of ATP. and purity decreases and ATTP
It has been found that the occurrence of this is the most difficult thing to remove in the post-treatment process.
そこで１本発明者等は醗酵法におけるＡＴＰの製造にお
いてＡＴＰの生成率が最大に達した時点ですみやかに副
反応の生起、特にＡＴＴＰの生起を中止すべき方法を種
々検討した結果、ＡＴＰの生成率が最大に達した時点の
醗酵液に極めて少量のフェノール性水酸基を有する化合
物を添加すると、その後の副反応をほとんど中止しうろ
ことを見い出し本発明を完成した。Therefore, the present inventors investigated various ways to stop the side reactions, especially the generation of ATTP, as soon as the production rate of ATP reaches the maximum in the production of ATP using the fermentation method. The inventors discovered that adding a very small amount of a compound having a phenolic hydroxyl group to the fermentation solution at the time when the fermentation rate reached its maximum can almost completely stop subsequent side reactions, thereby completing the present invention.
本発明に使用されろフェノール性水酸基を有する化合物
としてはフェノール、カテコール、レゾルシン、ヒドロ
キノン、ピロガロール、クロコツエノール、フロムフェ
ノール、ニトロフェノール。Compounds having a phenolic hydroxyl group that can be used in the present invention include phenol, catechol, resorcinol, hydroquinone, pyrogallol, crocotenol, fromphenol, and nitrophenol.
アミンフェノール、クレゾール、チモール、グアヤコー
ル、アセトフェノン、サリチル酸等がｈげられる。Amine phenol, cresol, thymol, guaiacol, acetophenone, salicylic acid, etc. are extracted.
これら各物質の添加濃度は、物質の種類。酵母の質およ
び量または醗酵培地により異なるが、醗酵液に対し０．
１〜２．０受で充分その効果を発揮する。The concentration of each of these substances added depends on the type of substance. Although it varies depending on the quality and quantity of yeast or the fermentation medium, 0.
A score of 1 to 2.0 is sufficient to demonstrate its effect.
なお１本酵素反応系において上述の７１ノール性水酸基
を醗酵初期より添加した場合、目的とするＡＴＰの生成
は全くみられないことから本発明方法は従来の酵素反応
において行われた適当な添加剤を加えろ収率改良或は醗
酵条件の改良とは異なるものである。Note that when the above-mentioned 71-nol hydroxyl group is added from the early stage of fermentation in this enzyme reaction system, the production of the target ATP is not observed at all. This is different from improving yield or improving fermentation conditions.
次に実施例を挙げて本発明を説明する。Next, the present invention will be explained with reference to Examples.
実施例 １モルリン酸緩衝液５００ｒｎｌ（ｐＨ６，１） 。Example 500 rnl of 1 molar phosphate buffer (pH 6.1).
グルコース４０ｇおよびアデノシン１６．５９’を水１
４００ｍ１に溶解し、それに８０係アセトアルデヒド３
．７９．ドルオール２０ＴＬｌを添加し、ｐＨ６，５に
調整し液温３６° Ｃに保つ。40g of glucose and 16.59' of adenosine in 1 part of water
Dissolve in 400 ml and add 3 80% acetaldehyde to it.
．． 79. Add 20 TL of Dorol, adjust the pH to 6.5, and maintain the liquid temperature at 36°C.
同温度で乾燥ビール酵母１００ｇ’を加え攪拌下醗酵さ
せる。At the same temperature, add 100g' of dry beer yeast and ferment with stirring.
経時的に醗酵液をサンプリングし、ＡＴＰ関連化合物を
定量する。The fermentation liquid is sampled over time and ATP-related compounds are quantified.
醗酵開始４時間後でＡＴＰ最大生成率を示した。The maximum ATP production rate was reached 4 hours after the start of fermentation.
その時点で醗酵液を分散し、フェノール性水酸基を有す
る化合物を各割合に添加し。At that point, the fermentation liquor is dispersed and the compound having a phenolic hydroxyl group is added in each proportion.
３６°Ｃで更に攪拌を継続し一定時間後の各成分の生成
率を測定した。Stirring was further continued at 36°C, and the production rate of each component was measured after a certain period of time.
４時間後、８時間後のＡＴＰ関連化合物の生成率は第１
表に示す通りである。The production rate of ATP-related compounds after 4 hours and 8 hours was the first
As shown in the table.
ＡＴＰの生成率が最大に達した時： ＡＭＰｏ、４係、ＡＤＰ２．１係、ＡＴＰ９７．Ｏ係。When the ATP production rate reaches its maximum: AMPo, 4th section, ADP2.1 section, ATP97. Person in charge of O.
ＡＴＴＰｏ、５係ATTPo, Section 5
Claims (1)
て、アゾン・／ントリリン酸の生成が最大に達した時点
でフェノール性水酸基を有する化合物を添加することを
特徴とする高純度アデノシンジリンリン酸の製法。1. A method for producing high-purity adenosine diphosphoric acid, which comprises adding a compound having a phenolic hydroxyl group at the time when the production of azone/ntriphosphoric acid reaches its maximum in the production of azone/ntriphosphoric acid by a fermentation method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8027276A JPS5939B2 (en) | 1976-07-06 | 1976-07-06 | Production method of high purity adenosine triphosphate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8027276A JPS5939B2 (en) | 1976-07-06 | 1976-07-06 | Production method of high purity adenosine triphosphate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS536490A JPS536490A (en) | 1978-01-20 |
| JPS5939B2 true JPS5939B2 (en) | 1984-01-05 |
Family
ID=13713640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8027276A Expired JPS5939B2 (en) | 1976-07-06 | 1976-07-06 | Production method of high purity adenosine triphosphate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5939B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT983691B (en) * | 1972-04-07 | 1974-11-11 | Hugin Kassaregister Ab | CHECKS TO A DEVICE TO INDIVIDUALLY DETECT CONTRAS CODED SIGNS FOR AUTOMATIC RECORDING AND READING |
-
1976
- 1976-07-06 JP JP8027276A patent/JPS5939B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS536490A (en) | 1978-01-20 |
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