CA1058213A - Method for the preparation of aminoacids - Google Patents
Method for the preparation of aminoacidsInfo
- Publication number
- CA1058213A CA1058213A CA249,437A CA249437A CA1058213A CA 1058213 A CA1058213 A CA 1058213A CA 249437 A CA249437 A CA 249437A CA 1058213 A CA1058213 A CA 1058213A
- Authority
- CA
- Canada
- Prior art keywords
- preparation
- aminoacids
- carbamyl
- alpha
- aminoacid
- 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
- 235000001014 amino acid Nutrition 0.000 title claims abstract description 20
- 150000001413 amino acids Chemical class 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims 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 claims abstract description 3
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 3
- 239000011347 resin Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 229940024606 amino acid Drugs 0.000 description 12
- 230000003287 optical effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-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
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- GIOUOHDKHHZWIQ-SSDOTTSWSA-N N-carbamoyl-D-phenylglycine Chemical compound NC(=O)N[C@@H](C(O)=O)C1=CC=CC=C1 GIOUOHDKHHZWIQ-SSDOTTSWSA-N 0.000 description 1
- DEWDMTSMCKXBNP-BYPYZUCNSA-N N-carbamoyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(N)=O DEWDMTSMCKXBNP-BYPYZUCNSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- LCQLHJZYVOQKHU-VKHMYHEASA-N carglumic acid Chemical compound NC(=O)N[C@H](C(O)=O)CCC(O)=O LCQLHJZYVOQKHU-VKHMYHEASA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 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 |
|---|---|
| CA1058213A true CA1058213A (en) | 1979-07-10 |
Family
ID=11192138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA249,437A Expired CA1058213A (en) | 1975-04-09 | 1976-04-02 | Method for the preparation of aminoacids |
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
Also Published As
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