JPS61282397A - グルタチオン及びγ−グルタミルシステインの精製法 - Google Patents
グルタチオン及びγ−グルタミルシステインの精製法Info
- Publication number
- JPS61282397A JPS61282397A JP12256685A JP12256685A JPS61282397A JP S61282397 A JPS61282397 A JP S61282397A JP 12256685 A JP12256685 A JP 12256685A JP 12256685 A JP12256685 A JP 12256685A JP S61282397 A JPS61282397 A JP S61282397A
- Authority
- JP
- Japan
- Prior art keywords
- glutamylcysteine
- glutathione
- acetic acid
- solution
- gluthathione
- 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
- 108010068906 gamma-glutamylcysteine Proteins 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims description 22
- RITKHVBHSGLULN-CRCLSJGQSA-N γ-glutamylcysteine Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@H](CS)C(O)=O RITKHVBHSGLULN-CRCLSJGQSA-N 0.000 title abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000003957 anion exchange resin Substances 0.000 claims abstract description 11
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract description 10
- 238000005342 ion exchange Methods 0.000 claims abstract description 3
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 3
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 129
- 108010024636 Glutathione Proteins 0.000 claims description 65
- 229960003180 glutathione Drugs 0.000 claims description 65
- RITKHVBHSGLULN-WHFBIAKZSA-N L-gamma-glutamyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(O)=O RITKHVBHSGLULN-WHFBIAKZSA-N 0.000 claims description 43
- 239000007788 liquid Substances 0.000 claims description 13
- PABVKUJVLNMOJP-WHFBIAKZSA-N Glu-Cys Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](CS)C(O)=O PABVKUJVLNMOJP-WHFBIAKZSA-N 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 abstract description 27
- 235000018417 cysteine Nutrition 0.000 abstract description 27
- 239000000243 solution Substances 0.000 abstract description 26
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 7
- 239000011347 resin Substances 0.000 abstract description 6
- 229920005989 resin Polymers 0.000 abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 5
- 238000002425 crystallisation Methods 0.000 abstract description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract description 5
- 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 abstract description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 abstract description 4
- 230000008025 crystallization Effects 0.000 abstract description 4
- 238000004108 freeze drying Methods 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 235000019253 formic acid Nutrition 0.000 abstract description 2
- 244000005700 microbiome Species 0.000 abstract description 2
- 239000003456 ion exchange resin Substances 0.000 abstract 2
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000002500 ions Chemical group 0.000 abstract 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 19
- 238000001962 electrophoresis Methods 0.000 description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000001879 copper Chemical class 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 229930189936 Glyoxalase Natural products 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 102000005367 Carboxypeptidases Human genes 0.000 description 1
- 108010006303 Carboxypeptidases Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 108010081687 Glutamate-cysteine ligase Proteins 0.000 description 1
- 102100039696 Glutamate-cysteine ligase catalytic subunit Human genes 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 108010036164 Glutathione synthase Proteins 0.000 description 1
- 102100034294 Glutathione synthetase Human genes 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 1
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZMZINYUKVRMNTG-UHFFFAOYSA-N acetic acid;formic acid Chemical compound OC=O.CC(O)=O ZMZINYUKVRMNTG-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 238000005842 biochemical reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Peptides Or Proteins (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12256685A JPS61282397A (ja) | 1985-06-07 | 1985-06-07 | グルタチオン及びγ−グルタミルシステインの精製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12256685A JPS61282397A (ja) | 1985-06-07 | 1985-06-07 | グルタチオン及びγ−グルタミルシステインの精製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61282397A true JPS61282397A (ja) | 1986-12-12 |
| JPH0533715B2 JPH0533715B2 (enrdf_load_stackoverflow) | 1993-05-20 |
Family
ID=14839065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12256685A Granted JPS61282397A (ja) | 1985-06-07 | 1985-06-07 | グルタチオン及びγ−グルタミルシステインの精製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61282397A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000030474A1 (fr) * | 1998-11-26 | 2000-06-02 | Ajinomoto Co., Inc. | Procede pour produire un renforçateur d'arome pour produits alimentaires |
| WO2016195070A1 (ja) * | 2015-06-05 | 2016-12-08 | 協和発酵バイオ株式会社 | 還元型グルタチオンのα型結晶の製造方法及び当該結晶の保存方法 |
| WO2017159555A1 (ja) | 2016-03-17 | 2017-09-21 | 協和発酵バイオ株式会社 | 還元型グルタチオンの結晶及びその製造方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3036974U (ja) * | 1996-10-17 | 1997-05-06 | 株式会社イモタニ | 入れ歯洗浄用容器 |
-
1985
- 1985-06-07 JP JP12256685A patent/JPS61282397A/ja active Granted
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000030474A1 (fr) * | 1998-11-26 | 2000-06-02 | Ajinomoto Co., Inc. | Procede pour produire un renforçateur d'arome pour produits alimentaires |
| US7118775B2 (en) | 1998-11-26 | 2006-10-10 | Ajinomoto Co., Inc. | Process for producing a flavor-enhancing material for foods |
| CN100366186C (zh) * | 1998-11-26 | 2008-02-06 | 味之素株式会社 | 食品风味增强用原材料的制造方法 |
| JPWO2016195070A1 (ja) * | 2015-06-05 | 2018-03-22 | 協和発酵バイオ株式会社 | 還元型グルタチオンのα型結晶の製造方法及び当該結晶の保存方法 |
| CN107636006A (zh) * | 2015-06-05 | 2018-01-26 | 协和发酵生化株式会社 | 还原型谷胱甘肽的α型晶体的生产方法和所述晶体的保存方法 |
| WO2016195070A1 (ja) * | 2015-06-05 | 2016-12-08 | 協和発酵バイオ株式会社 | 還元型グルタチオンのα型結晶の製造方法及び当該結晶の保存方法 |
| EP3305801A4 (en) * | 2015-06-05 | 2019-01-23 | Kyowa Hakko Bio Co., Ltd. | PROCESS FOR PREPARING AN ALPHA FORM CRYSTAL FROM REDUCED GLUTATHION AND METHOD FOR STORING THE SAID CRYSTAL |
| US10407463B2 (en) | 2015-06-05 | 2019-09-10 | Kyowa Hakko Bio Co., Ltd. | Method for producing alpha-form crystal of reduced glutathione, and method for storing said crystal |
| JP2021080265A (ja) * | 2015-06-05 | 2021-05-27 | 協和発酵バイオ株式会社 | 還元型グルタチオンのα型結晶の製造方法及び当該結晶の保存方法 |
| CN107636006B (zh) * | 2015-06-05 | 2021-11-09 | 协和发酵生化株式会社 | 还原型谷胱甘肽的α型晶体的生产方法和所述晶体的保存方法 |
| EP4406960A3 (en) * | 2015-06-05 | 2025-01-08 | Kyowa Hakko Bio Co., Ltd. | Method for producing alpha-form crystal of reduced glutathione, and method for storing said crystal |
| WO2017159555A1 (ja) | 2016-03-17 | 2017-09-21 | 協和発酵バイオ株式会社 | 還元型グルタチオンの結晶及びその製造方法 |
| US10858393B2 (en) | 2016-03-17 | 2020-12-08 | Kyowa Hakko Bio Co., Ltd. | Crystal of reduced glutathione and method for producing same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0533715B2 (enrdf_load_stackoverflow) | 1993-05-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |