JPH0439454B2 - - Google Patents
Info
- Publication number
- JPH0439454B2 JPH0439454B2 JP12002283A JP12002283A JPH0439454B2 JP H0439454 B2 JPH0439454 B2 JP H0439454B2 JP 12002283 A JP12002283 A JP 12002283A JP 12002283 A JP12002283 A JP 12002283A JP H0439454 B2 JPH0439454 B2 JP H0439454B2
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- crystals
- phenylalanine
- monosodium
- pentahydrate
- 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
- 239000013078 crystal Substances 0.000 claims description 101
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 54
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 29
- 239000007788 liquid Substances 0.000 claims description 22
- 238000002425 crystallisation Methods 0.000 claims description 20
- 230000008025 crystallization Effects 0.000 claims description 20
- OXOIFZVQCYLLIV-BXOSLQCASA-N O.O.O.O.O.[Na].N[C@@H](CC1=CC=CC=C1)C(=O)O Chemical compound O.O.O.O.O.[Na].N[C@@H](CC1=CC=CC=C1)C(=O)O OXOIFZVQCYLLIV-BXOSLQCASA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 229910001415 sodium ion Inorganic materials 0.000 claims description 16
- 238000000855 fermentation Methods 0.000 claims description 14
- 230000004151 fermentation Effects 0.000 claims description 14
- 150000004686 pentahydrates Chemical class 0.000 claims description 14
- IRDKFMIMLZOUHA-JZGIKJSDSA-N (2s)-2-amino-3-phenylpropanoic acid;sodium;hydrate Chemical compound O.[Na].OC(=O)[C@@H](N)CC1=CC=CC=C1 IRDKFMIMLZOUHA-JZGIKJSDSA-N 0.000 claims description 11
- 230000007704 transition Effects 0.000 claims description 11
- 150000004682 monohydrates Chemical class 0.000 claims description 7
- 239000002002 slurry Substances 0.000 claims description 7
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 5
- 238000007710 freezing Methods 0.000 claims description 4
- 230000008014 freezing Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 claims 1
- 229960005190 phenylalanine Drugs 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 12
- 239000012535 impurity Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 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 description 4
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- 229960004441 tyrosine Drugs 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 3
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000003798 L-tyrosyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002993 phenylalanine derivatives Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 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
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- ZRVUAXXSASAVFG-QRPNPIFTSA-M sodium;(2s)-2-amino-3-phenylpropanoate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CC1=CC=CC=C1 ZRVUAXXSASAVFG-QRPNPIFTSA-M 0.000 description 1
- IMPPALRZVJRGTC-JZGIKJSDSA-M sodium;(2s)-2-amino-3-phenylpropanoate;hydrate Chemical compound O.[Na+].[O-]C(=O)[C@@H](N)CC1=CC=CC=C1 IMPPALRZVJRGTC-JZGIKJSDSA-M 0.000 description 1
- HQAITFAUVZBHNB-UHFFFAOYSA-N sodium;pentahydrate Chemical compound O.O.O.O.O.[Na] HQAITFAUVZBHNB-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12002283A JPS6013746A (ja) | 1983-07-01 | 1983-07-01 | 新規フェニルアラニン塩結晶とその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12002283A JPS6013746A (ja) | 1983-07-01 | 1983-07-01 | 新規フェニルアラニン塩結晶とその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6013746A JPS6013746A (ja) | 1985-01-24 |
| JPH0439454B2 true JPH0439454B2 (pt) | 1992-06-29 |
Family
ID=14775968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12002283A Granted JPS6013746A (ja) | 1983-07-01 | 1983-07-01 | 新規フェニルアラニン塩結晶とその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6013746A (pt) |
-
1983
- 1983-07-01 JP JP12002283A patent/JPS6013746A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6013746A (ja) | 1985-01-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3694921B2 (ja) | バリンの精製法 | |
| RU1774951C (ru) | Способ выделени кето-2-L-гулоновой кислоты из ферментационного сусла | |
| JPH10237030A (ja) | 分岐鎖アミノ酸の精製法 | |
| JPH08157433A (ja) | 塩基性アミノ酸の精製方法 | |
| US4399304A (en) | L-phenylalanine 1/2 sulfate and its use | |
| US5618936A (en) | Process for preparing (S) (+)-4,4'-(1-methyl-1,2-ethanediyl)-bis (2,6-piperazinedione) | |
| JPH0439454B2 (pt) | ||
| CN110885357B (zh) | 一种纳滤膜分离纯化丙谷二肽的方法 | |
| JPS5939857A (ja) | アミノ酸の晶析方法 | |
| JPH0657719B2 (ja) | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルの回収方法 | |
| JP2971664B2 (ja) | ペプチド類からアミノ酸を回収する方法 | |
| US4582928A (en) | Process for producing optically active phenylalanine | |
| JPS6338B2 (pt) | ||
| JPS604168A (ja) | トリプトフアンの晶析法 | |
| US4588818A (en) | Method for recovery of optically active tryptophane | |
| JPS6258345B2 (pt) | ||
| JPS626702B2 (pt) | ||
| JPH0267256A (ja) | カルニチンおよびカルニチンニトリルの単離精製法 | |
| JPH0352455B2 (pt) | ||
| JPS604155A (ja) | Ｌ−ロイシンおよびｌ−イソロイシンの分離法 | |
| KR850000717B1 (ko) | 단백질 가수분해 산물로 부터의 아미노산의 회수방법 | |
| JPS63130580A (ja) | トリプトフアンの精製法 | |
| JPS6032752A (ja) | 光学活性フェニルアラニンの製造方法 | |
| JPH0342268B2 (pt) | ||
| KR820001129B1 (ko) | L-글루타민산 발효액에서 글루타민산을 회수하는 방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |