CH620421A5 - Process for preparing amino acids - Google Patents
Process for preparing amino acids Download PDFInfo
- Publication number
- CH620421A5 CH620421A5 CH423676A CH423676A CH620421A5 CH 620421 A5 CH620421 A5 CH 620421A5 CH 423676 A CH423676 A CH 423676A CH 423676 A CH423676 A CH 423676A CH 620421 A5 CH620421 A5 CH 620421A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbamyl
- amino acid
- acid
- resin
- optical purity
- Prior art date
Links
- 150000001413 amino acids Chemical class 0.000 title claims 16
- 238000004519 manufacturing process Methods 0.000 title 1
- 229940024606 amino acid Drugs 0.000 claims 15
- 235000001014 amino acid Nutrition 0.000 claims 15
- 239000011347 resin Substances 0.000 claims 10
- 229920005989 resin Polymers 0.000 claims 10
- 238000000034 method Methods 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 230000003287 optical effect Effects 0.000 claims 7
- 239000007800 oxidant agent Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 4
- 230000001590 oxidative effect Effects 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- 125000002091 cationic group Chemical group 0.000 claims 3
- 239000003456 ion exchange resin Substances 0.000 claims 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims 3
- 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 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- 229960004295 valine Drugs 0.000 claims 2
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 claims 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 1
- 229930195722 L-methionine Natural products 0.000 claims 1
- DEWDMTSMCKXBNP-BYPYZUCNSA-N N-carbamoyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(N)=O DEWDMTSMCKXBNP-BYPYZUCNSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- LCQLHJZYVOQKHU-VKHMYHEASA-N carglumic acid Chemical compound NC(=O)N[C@H](C(O)=O)CCC(O)=O LCQLHJZYVOQKHU-VKHMYHEASA-N 0.000 claims 1
- 229920001429 chelating resin Polymers 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 239000008367 deionised water Substances 0.000 claims 1
- 229910021641 deionized water Inorganic materials 0.000 claims 1
- 230000007071 enzymatic hydrolysis Effects 0.000 claims 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229960002989 glutamic acid Drugs 0.000 claims 1
- 150000001469 hydantoins Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 229960004452 methionine Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000006340 racemization Effects 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- 230000000707 stereoselective effect Effects 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
- C07C227/20—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters by hydrolysis of N-acylated amino-acids or derivatives thereof, e.g. hydrolysis of carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22144/75A IT1037176B (it) | 1975-04-09 | 1975-04-09 | Procedimento per la preparazione di ammindacidi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH620421A5 true CH620421A5 (en) | 1980-11-28 |
Family
ID=11192138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH423676A CH620421A5 (en) | 1975-04-09 | 1976-04-05 | Process for preparing amino acids |
Country Status (38)
| Country | Link |
|---|---|
| JP (1) | JPS5940823B2 (da) |
| AR (1) | AR217052A1 (da) |
| AT (1) | AT343092B (da) |
| AU (1) | AU503651B2 (da) |
| BE (1) | BE840527A (da) |
| BG (1) | BG24664A3 (da) |
| BR (1) | BR7602173A (da) |
| CA (1) | CA1058213A (da) |
| CH (1) | CH620421A5 (da) |
| CS (1) | CS194756B2 (da) |
| DD (1) | DD123599A5 (da) |
| DE (1) | DE2615594C3 (da) |
| DK (1) | DK146622C (da) |
| EG (1) | EG12543A (da) |
| ES (1) | ES447176A1 (da) |
| FR (1) | FR2306976A1 (da) |
| GB (1) | GB1490054A (da) |
| HU (1) | HU176009B (da) |
| IE (1) | IE42673B1 (da) |
| IL (1) | IL49372A (da) |
| IN (1) | IN144346B (da) |
| IT (1) | IT1037176B (da) |
| LU (1) | LU74714A1 (da) |
| MW (1) | MW1076A1 (da) |
| MX (1) | MX3304E (da) |
| MY (1) | MY7900100A (da) |
| NL (1) | NL7603816A (da) |
| NO (1) | NO143901C (da) |
| PH (1) | PH12101A (da) |
| PL (1) | PL104015B1 (da) |
| PT (1) | PT64983B (da) |
| RO (1) | RO70427A (da) |
| SE (1) | SE409701B (da) |
| SU (1) | SU670213A3 (da) |
| TR (1) | TR18877A (da) |
| YU (1) | YU90376A (da) |
| ZA (1) | ZA761941B (da) |
| ZM (1) | ZM4476A1 (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS584707B2 (ja) * | 1977-02-21 | 1983-01-27 | 鐘淵化学工業株式会社 | 光学活性フエニルグリシン類の製造法 |
| IT1204979B (it) * | 1987-04-28 | 1989-03-10 | Eniricerche Spa | Sintesi di alfa amminoacidi otticamente attivi |
| FR2725991B1 (fr) * | 1994-10-24 | 1997-01-17 | Univ Montpellier Ii | Procede de synthese peptidique a partir des n-(n'-(r')-n' -nitrosocarbamoyls) aminoacides |
| CN1057518C (zh) * | 1995-09-29 | 2000-10-18 | 中国科学院微生物研究所 | 氮－氨甲酰基氨基酸热水解制备光学活性氨基酸的方法 |
| US6087136A (en) * | 1997-03-31 | 2000-07-11 | Council Of Scientific & Industrial Research | Microbial process for the production of D(-)-N-carbamoylphenylglycine |
| CN105601542B (zh) * | 2016-01-08 | 2017-10-24 | 南京工业大学 | 一种混酸结晶n‑氨甲酰谷氨酸的方法 |
-
1975
- 1975-04-09 IT IT22144/75A patent/IT1037176B/it active
-
1976
- 1976-03-31 DK DK154676A patent/DK146622C/da not_active IP Right Cessation
- 1976-03-31 ZA ZA761941A patent/ZA761941B/xx unknown
- 1976-04-01 MW MW10/76A patent/MW1076A1/xx unknown
- 1976-04-02 CA CA249,437A patent/CA1058213A/en not_active Expired
- 1976-04-05 ZM ZM44/76A patent/ZM4476A1/xx unknown
- 1976-04-05 CH CH423676A patent/CH620421A5/it not_active IP Right Cessation
- 1976-04-05 AU AU12648/76A patent/AU503651B2/en not_active Expired
- 1976-04-05 EG EG196/76A patent/EG12543A/xx active
- 1976-04-06 TR TR18877A patent/TR18877A/xx unknown
- 1976-04-06 GB GB13783/76A patent/GB1490054A/en not_active Expired
- 1976-04-07 FR FR7610087A patent/FR2306976A1/fr active Granted
- 1976-04-07 PT PT64983A patent/PT64983B/pt unknown
- 1976-04-07 LU LU74714A patent/LU74714A1/xx unknown
- 1976-04-07 NO NO761189A patent/NO143901C/no unknown
- 1976-04-07 DD DD192242A patent/DD123599A5/xx unknown
- 1976-04-08 IN IN611/CAL/76A patent/IN144346B/en unknown
- 1976-04-08 YU YU00903/76A patent/YU90376A/xx unknown
- 1976-04-08 CS CS762334A patent/CS194756B2/cs unknown
- 1976-04-08 BR BR7602173A patent/BR7602173A/pt unknown
- 1976-04-08 PH PH18315A patent/PH12101A/en unknown
- 1976-04-08 HU HU76SA2914A patent/HU176009B/hu unknown
- 1976-04-08 BE BE165963A patent/BE840527A/xx not_active IP Right Cessation
- 1976-04-08 AT AT258276A patent/AT343092B/de not_active IP Right Cessation
- 1976-04-08 IE IE737/76A patent/IE42673B1/en unknown
- 1976-04-08 IL IL49372A patent/IL49372A/xx unknown
- 1976-04-09 RO RO7685571A patent/RO70427A/ro unknown
- 1976-04-09 DE DE2615594A patent/DE2615594C3/de not_active Expired
- 1976-04-09 SU SU762343157A patent/SU670213A3/ru active
- 1976-04-09 SE SE7604237A patent/SE409701B/xx unknown
- 1976-04-09 BG BG032860A patent/BG24664A3/xx unknown
- 1976-04-09 MX MX000157U patent/MX3304E/es unknown
- 1976-04-09 ES ES447176A patent/ES447176A1/es not_active Expired
- 1976-04-09 PL PL1976188626A patent/PL104015B1/pl unknown
- 1976-04-09 NL NL7603816A patent/NL7603816A/xx active Search and Examination
- 1976-04-09 JP JP51039420A patent/JPS5940823B2/ja not_active Expired
- 1976-04-09 AR AR262843A patent/AR217052A1/es active
-
1979
- 1979-12-30 MY MY100/79A patent/MY7900100A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: ANIC S.P.A. |
|
| PL | Patent ceased |