SU670213A3 - Method of producing optically active amino acids - Google Patents
Method of producing optically active amino acidsInfo
- Publication number
- SU670213A3 SU670213A3 SU762343157A SU2343157A SU670213A3 SU 670213 A3 SU670213 A3 SU 670213A3 SU 762343157 A SU762343157 A SU 762343157A SU 2343157 A SU2343157 A SU 2343157A SU 670213 A3 SU670213 A3 SU 670213A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- amino acids
- optically active
- active amino
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 6
- 150000001413 amino acids Chemical class 0.000 title description 4
- 230000003287 optical effect Effects 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- -1 -8.01 ° (c 0.8 Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BJKZXRGDVGYJTP-UHFFFAOYSA-N anilino acetate Chemical compound CC(=O)ONC1=CC=CC=C1 BJKZXRGDVGYJTP-UHFFFAOYSA-N 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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)
Description
(54)(54)
СПОСОБ ПОЛУЧЕНИЯ ОПТИЧЕСКИ АКТИВНЫХ АМИНОКИСЛОТMETHOD OF OBTAINING OPTICALLY ACTIVE AMINO ACIDS
водное, наход щеес в избытке по отношению к его растворимости, выпадает в осадок. До- бавл ют 1-1,5 эквивалента окислител , азотистую кислоту или ее соль, при этом температуру поддерживают в интервале 0-40°С. После свершени реакции аминокислоту вымывают из смолы основанием, после этого сама смола вновь может быть возвращена в кислую форму. Из элюирующего раствора аминокислоту отдел ют простым концентрированием или перекристал- ю water, which is in excess with respect to its solubility, precipitates. 1-1.5 equivalents of oxidant, nitrous acid or its salt are added, while the temperature is maintained in the range of 0-40 ° C. After the reaction is completed, the amino acid is washed out of the resin with a base, after which the resin itself can again be returned to the acidic form. From the elution solution, the amino acid is separated by simple concentration or recrystal
лизациеи.lizatsii.
Целевые продукты получают с высоким выходом и очень высокой оптической чистотой.Target products are obtained with high yield and very high optical purity.
И р и м е Pi I. 194 г (1 моль) D-N-карбамилфениламиноуксусной кислоты оптической чистоты 99% перемешивают с 10 л деионизованной воды в присутствии 8 л Амберлита LR 120 (Н ). К перемешиваемому раствору, при комнатной температуре, добавл ют 83 г (1,2 мол ) нитрита натри . Спуст примерно два часа смолу отфильтровывают, дважды промывают 10 л ум гченной воды и затем перенос т в колонку (диаметр 11 см и высота 1 м). Смолу элюируют 2 н. аммиачной водой.And pI m e Pi I. 194 g (1 mol) of D-N-carbamylphenylaminoacetic acid of optical purity 99% mixed with 10 l of deionized water in the presence of 8 l of Amberlite LR 120 (H). 83 g (1.2 mol) of sodium nitrite is added to the stirred solution at room temperature. After about two hours, the resin is filtered off, washed twice with 10 liters of softened water and then transferred to a column (diameter 11 cm and height 1 m). The resin was eluted with 2N. ammonia water.
Раствор 5 л аммониевой соли О-фениламиноуксусной кислоты упаривают досуха при пониженном давлении. В результате получают 150 г (99% от теоретического) D-фениламиноуксусной кислоты, а 157° (с 0,5, 1 н. НС1),т.е с оптической чистотой вьште 98%.A solution of 5 L of the ammonium salt of O-phenylaminoacetic acid is evaporated to dryness under reduced pressure. The result is 150 g (99% of theoretical) of D-phenylaminoacetic acid, and 157 ° (with 0.5, 1 N. HC1), that is, with an optical purity of 98%.
П р и м е р 2. По выше описанной методике , что и в примере 1, использу в качестве исходного вещества - 132 г (1 моль) L-Nкарбамил-а-аминонропионовой кислоты оптической чистоты 98%, получают 87 г (0,98 мол ) Ьа-аминонропионовой кислоты, а +14,3° (с 2, 1 н. HCI).PRI mme R 2. According to the above described procedure, as in Example 1, using 132 g (1 mol) of L-N-carbamyl-a-aminonropionic acid of optical purity 98% as the starting material, 87 g (0, 98 mol) of LA-aminopropionic acid, and + 14.3 ° (with 2, 1 N. HCl).
Примерз. По выше описа1шой методике; что и в примере 1. использу в качестве исходного вещества 160 г (1 моль) L-N-карбамил-а-аминоизовалериановой кислоты оптической чистоты 97%, получают ПО г (0,94 мол ) L-a-аминоизовалериановой кислоты, fa 28,2° (с 3, 6 н. HCI).Froze According to the above method; as in example 1. using 160 g (1 mol) of LN-carbamyl-a-aminoisovaleric acid of optical purity 97% as the starting material, one obtains PO g (0.94 mol) of La-aminoisovaleric acid, fa 28.2 ° ( from 3, 6 N. HCI).
П р и м е р 4. По выше описанной методике что и в примере 1, в качестве исходного вещества используют 192 г (I моль) L-N-карбамил-а-амино-7-метилтиомасл ной кислоты.EXAMPLE 4 According to the above described procedure as in Example 1, 192 g (I mol) of L-N-carbamyl-a-amino-7-methylthiobutyric acid are used as the starting material.
Получают 145 г (0,97 мол ) ;. и-а-амино-у-метилтиомасл ной кислоты, -8,01° (с 0,8, вода).Obtain 145 g (0.97 mole);. a-a-amino-y-methylthiobutyric acid, -8.01 ° (c 0.8, water).
Пример 5. .Следу той же методике , что и в примере 1, и использу в качестве исходного вещества 130 г (1 моль) L-IM-карбамилглутаминовой кислоты оптической чистоты 98%, получают 183 г (0,96 мол ) L-глутаминовой кислоты, )° 31° (с I, 6 н. HCI).Example 5. Following the same procedure as in Example 1, and using 130 g (1 mol) of L-IM-carbamylglutamic acid of 98% optical purity as the starting material, 183 g (0.96 mol) of L-glutamic acid are obtained. acids,) ° 31 ° (with I, 6 N. HCI).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22144/75A IT1037176B (en) | 1975-04-09 | 1975-04-09 | PROCEDURE FOR THE PREPARATION OF AMINDACIDS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU670213A3 true SU670213A3 (en) | 1979-06-25 |
Family
ID=11192138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762343157A SU670213A3 (en) | 1975-04-09 | 1976-04-09 | Method of producing optically active amino acids |
Country Status (38)
| Country | Link |
|---|---|
| JP (1) | JPS5940823B2 (en) |
| AR (1) | AR217052A1 (en) |
| AT (1) | AT343092B (en) |
| AU (1) | AU503651B2 (en) |
| BE (1) | BE840527A (en) |
| BG (1) | BG24664A3 (en) |
| BR (1) | BR7602173A (en) |
| CA (1) | CA1058213A (en) |
| CH (1) | CH620421A5 (en) |
| CS (1) | CS194756B2 (en) |
| DD (1) | DD123599A5 (en) |
| DE (1) | DE2615594C3 (en) |
| DK (1) | DK146622C (en) |
| EG (1) | EG12543A (en) |
| ES (1) | ES447176A1 (en) |
| FR (1) | FR2306976A1 (en) |
| GB (1) | GB1490054A (en) |
| HU (1) | HU176009B (en) |
| IE (1) | IE42673B1 (en) |
| IL (1) | IL49372A (en) |
| IN (1) | IN144346B (en) |
| IT (1) | IT1037176B (en) |
| LU (1) | LU74714A1 (en) |
| MW (1) | MW1076A1 (en) |
| MX (1) | MX3304E (en) |
| MY (1) | MY7900100A (en) |
| NL (1) | NL7603816A (en) |
| NO (1) | NO143901C (en) |
| PH (1) | PH12101A (en) |
| PL (1) | PL104015B1 (en) |
| PT (1) | PT64983B (en) |
| RO (1) | RO70427A (en) |
| SE (1) | SE409701B (en) |
| SU (1) | SU670213A3 (en) |
| TR (1) | TR18877A (en) |
| YU (1) | YU90376A (en) |
| ZA (1) | ZA761941B (en) |
| ZM (1) | ZM4476A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS584707B2 (en) * | 1977-02-21 | 1983-01-27 | 鐘淵化学工業株式会社 | Method for producing optically active phenylglycines |
| IT1204979B (en) * | 1987-04-28 | 1989-03-10 | Eniricerche Spa | SUMMARY OF OPTICALLY ACTIVE ALPHA AMINO ACIDS |
| FR2725991B1 (en) * | 1994-10-24 | 1997-01-17 | Univ Montpellier Ii | PROCESS FOR PEPTIDE SYNTHESIS FROM N- (N '- (R') - N '-NITROSOCARBAMOYLS) AMINOACIDS |
| CN1057518C (en) * | 1995-09-29 | 2000-10-18 | 中国科学院微生物研究所 | Process for preparation of optically active amino-acid by hot- hydrolysis of nitrogen-ammonia formyl-amino acid |
| US6087136A (en) * | 1997-03-31 | 2000-07-11 | Council Of Scientific & Industrial Research | Microbial process for the production of D(-)-N-carbamoylphenylglycine |
| CN105601542B (en) * | 2016-01-08 | 2017-10-24 | 南京工业大学 | Method for crystallizing N-carbamylglutamic acid by using mixed acid |
-
1975
- 1975-04-09 IT IT22144/75A patent/IT1037176B/en active
-
1976
- 1976-03-31 DK DK154676A patent/DK146622C/en not_active IP Right Cessation
- 1976-03-31 ZA ZA761941A patent/ZA761941B/en unknown
- 1976-04-01 MW MW10/76A patent/MW1076A1/en unknown
- 1976-04-02 CA CA249,437A patent/CA1058213A/en not_active Expired
- 1976-04-05 ZM ZM44/76A patent/ZM4476A1/en unknown
- 1976-04-05 CH CH423676A patent/CH620421A5/en 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/en active
- 1976-04-06 TR TR18877A patent/TR18877A/en unknown
- 1976-04-06 GB GB13783/76A patent/GB1490054A/en not_active Expired
- 1976-04-07 FR FR7610087A patent/FR2306976A1/en active Granted
- 1976-04-07 PT PT64983A patent/PT64983B/en unknown
- 1976-04-07 LU LU74714A patent/LU74714A1/xx unknown
- 1976-04-07 NO NO761189A patent/NO143901C/en 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/en unknown
- 1976-04-08 CS CS762334A patent/CS194756B2/en unknown
- 1976-04-08 BR BR7602173A patent/BR7602173A/en unknown
- 1976-04-08 PH PH18315A patent/PH12101A/en unknown
- 1976-04-08 HU HU76SA2914A patent/HU176009B/en unknown
- 1976-04-08 BE BE165963A patent/BE840527A/en not_active IP Right Cessation
- 1976-04-08 AT AT258276A patent/AT343092B/en not_active IP Right Cessation
- 1976-04-08 IE IE737/76A patent/IE42673B1/en unknown
- 1976-04-08 IL IL49372A patent/IL49372A/en unknown
- 1976-04-09 RO RO7685571A patent/RO70427A/en unknown
- 1976-04-09 DE DE2615594A patent/DE2615594C3/en not_active Expired
- 1976-04-09 SU SU762343157A patent/SU670213A3/en active
- 1976-04-09 SE SE7604237A patent/SE409701B/en unknown
- 1976-04-09 BG BG032860A patent/BG24664A3/en unknown
- 1976-04-09 MX MX000157U patent/MX3304E/en unknown
- 1976-04-09 ES ES447176A patent/ES447176A1/en not_active Expired
- 1976-04-09 PL PL1976188626A patent/PL104015B1/en unknown
- 1976-04-09 NL NL7603816A patent/NL7603816A/en active Search and Examination
- 1976-04-09 JP JP51039420A patent/JPS5940823B2/en not_active Expired
- 1976-04-09 AR AR262843A patent/AR217052A1/en active
-
1979
- 1979-12-30 MY MY100/79A patent/MY7900100A/en unknown
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