IE42673B1 - Production of amino acids - Google Patents
Production of amino acidsInfo
- Publication number
- IE42673B1 IE42673B1 IE737/76A IE73776A IE42673B1 IE 42673 B1 IE42673 B1 IE 42673B1 IE 737/76 A IE737/76 A IE 737/76A IE 73776 A IE73776 A IE 73776A IE 42673 B1 IE42673 B1 IE 42673B1
- Authority
- IE
- Ireland
- Prior art keywords
- amino acid
- process according
- acid
- carbamoyl
- derivative
- Prior art date
Links
- 150000001413 amino acids Chemical class 0.000 title claims abstract description 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 13
- 229920005989 resin Polymers 0.000 claims abstract description 13
- 239000011347 resin Substances 0.000 claims abstract description 13
- 239000007800 oxidant agent Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims 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 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 238000005342 ion exchange Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 229940024606 amino acid Drugs 0.000 description 19
- 235000001014 amino acid Nutrition 0.000 description 18
- 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
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-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
- 229920001429 chelating resin Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
- 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
- 235000004279 alanine Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 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
- 150000001875 compounds Chemical class 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
- 230000003292 diminished effect Effects 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 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)
Abstract
The technical problem of preparing amino acids from carbamyl derivatives thereof is solved by reacting such a derivative, which may have been converted to a salt, with an oxidising agent such as nitrous acid in the presence of a cation resin in the acid form.
Description
This invention relates to a process for producing amino acids starting from the corresponding carbamoyl derivative of the amino acids.
Our British Patent Specification No. 1,452,591 describes and claims a process for producing optically active carbamoyl derivatives of amino acids from the corresponding racemic hydantoins by stereo-selective enzymic hydrolysis. The carbamoyl derivatives thus obtained can then be converted into the corresponding amino acid merely by boiling the derivative in an aqueous solution.
However, the hydrolysis of the carbamoyl derivatives to the amino acid under such conditions can be slow and can require a strict control of the operating conditions, and can sometimes give rise to by-products with a resulting lowering of the yield and even partial racemization.
The present invention provides a process for producing an «-amino acid, which comprises reacting the N-carbamoyl derivative of the desired amino acid, or a salt of such a derivative, with an oxidizing agent in the presence of an acid-group-containing ion-exchange resin.
By means of the present invention, the conversion of the carbamoyl derivative to the corresponding amino acid, can take place under mild conditions such that the resulting amino acid retains the optical purity of the starting carbamoyl derivative. - 2 4 ««7 3 The results which can be obtained by the present invention are surprising inasmuch as it is known that by merely reacting the carbamoyl derivative of an amino acid with an oxidizing substance, the desired amino acid is produced, but the amino group of the amino acid is immediately converted to a hydroxy group to give the corresponding hydroxy acid, thus making it impossible satisfactorily to convert the carbamoyl derivative to its amino acid.
In contrast, it has been observed that, when operating in the presence of cationic resins, in accordance with the present invention, under appropriate pH and temperature conditions, surprisingly high yields can be achieved inasmuch as the aminoacid is completely exempt from attack by the oxidizing reactant.
The process of the present invention can be carried out by dissolving the carbamoyl derivative, or a salt thereof, in water at a suitable concentration, preferably near saturation. The solution is supplemented by a quantity of a cationic resin in its acidic form preferably having such an exchange capacity as to bind from 100 to 500% of the amino acid product. During this step, the pH is generally lowered and the carbamoyl derivative, in an excess amount relative to its solubility, is precipitated. There are generally added from 1 to 1.5 equivalents of oxidizing agent per mole of carbamoyl derivative, the whole operation generally being conducted at a temperature in the range from 0°C to 40°C.
As cationic resins, there can be used resins with various acidic groups, although sulphonic type resins are preferably used. Also, the oxidizing agent can be any suitable oxidizing agent, although the use of nitrous acid or a salt thereof is preferred.
On completion of the reaction, the amino acid can be eluted from the resin with a base, after which the resin can be brought to its acidic form again; from the eluate, the amino acid can be isolated by simple concentration and crystallization operations. - 3 . 5 Ι«·?3 The present invention will now be illustrated by the following Examples 2 to 6, Example 1 being included for comparative purposes.
EXAMPLE 1 (Comparative) Millilitres of a 25 mM solution of N-carbamoyl-alpha-alanine were treated at 0°C with 5 ml of a 50 mM solution of NaNOg in water. The concentration of the amino acid (i.e. alanine) in the solution was occasionally measured. The concentration reached a maximum of 5 mM in the first hour of the reaction, and after that slowly diminished so that after 5 hours it had fallen to 3.2 mM.
Chromatographic analysis of the mixture showed the presence of a considerable quantity of lactic acid.
EXAMPLE 2. 194 Grams (1 mole) of D-N-carbamoyl-phenylglycine having an optical purity of 99% were slurried in 10 litres of deionized water, in the presence of 8 litres Amberlite I.R. 120 (H+), which is a phenol-methylene sulphonic resin.
The word '‘Amberlite is a Registered Trade Mark. The solution was stirred at room temperature and to it were added 83 grams (1.2 mole) of sodium nitrite.
After about 2 hours, the resin was filtered off, washed twice with 10 litres of demineralized water and then transferred to a column having a diameter of 11 centimetres and a height of 1 metre. The resin was then eluted with 2 mM ammonia; the amino acid was present in its entirety in the fraction from 10 to 15 litres of eluate.
The resulting solution of the ammonium salt of D-phenylglycine, in volume 5 litres, was evaporated under reduced pressure to dryness. There were ΟΛ thus obtained 150 grams (99% of theory) of D(-)phenylglycine having an (« )D = 157° (C = 0.5; HCl IN), that is an optical purity higher than 98% by taking as ?n the («t)D the data of the technical literature (Org. Synth. 22, 23, 1942). EXAMPLE 3.
By adopting the same procedure as set forth in Example 2, but starting from 132 grams (1 mole) of L-N-carbamoyl-alpha-alanine having an optical purity of on 98% there were obtained 87 grams (0.98 mole) of L-alpha-alanine with an ( D = - 4 4***3. 14.3° (c = 2, HCl IN); from the literature ( ο<· )θ15 = + 14.7°, according to J. Chem. Soc. 113, 526, 1918, for the pure compound.
EXAMPLE 4.
Following the same procedure as described in Example 2, but starting from 160 grams (1 mole) of L-N-carbamoyl valine with an optical purity of 97%, there were obtained 110 grams (0.94 mole) of L-valine; ( ot )^20 = 28.2° (c 3; HC1 6 NJ: according to Ber. 39, 2320, 1906, ( «* )θ2θ = 28.8° for the pure isomer.
EXAMPLE 5.
By following the same procedure as described in Example 2, from 192 grams (1 mole) of L-N-carbamoyl methionine, having an optical purity as high as 99%, there were obtained 145 grams (0.97 mole) of L-methionine; ( -)n^ ~ minus 8.01° (c - 0.8, water); according to J. Am. Chem. Soc., 53, u 25 3490, 1931, ( « )D = minus 8.01° for the pure isomer.
EXAMPLE 6.
Following the same procedure as described in Example 2, from 190 grams (1 mole) of L-N-carbamoyl glutamic acid having an optical purity of 98%, there were obtained about 141 grams (about 0.96 mole) of L-glutamic acid; ( « )D20 = 31° (c = 1; HC1 6N); according to Ber., 40, 3717, 1907, ( « )Q12 = + 31,2°, for the pure isomer.
Claims (8)
1. A process for producing an «-amino acid, which comprises reacting the N-carbamoyl derivative of the desired amino acid, or a salt of such a derivative, with an oxidizing agent in the presence of an acid-group-containing ion-exchange 25 resin.
2. A process according to Claim 1, wherein the reaction is conducted in the presence of an amount of oxidizing agent in the range from 1 to 1.5 equivalents per mole of carbamoyl derivative.
3. A process according to Claim 1 or 2, wherein the reaction is conducted 30 at a temperature in the range from 0°C to 40°C. - 5 4»t*3
4. A process according to any preceding claim, wherein the resin used is of the sulphonic type.
5. A process according to any preceding claim, wherein the oxidizing agent is nitrous acid or a salt thereof.
6. A process according to any preceding claim, where the acid-groupcontaining ion-exchange resin is used in an amount sufficient to absorb from 100 to 500% of the amino acid produced in the reaction.
7. A process according to Claim 1, substantially as described iri any one of the foregoing Examples 2 to 6.
8. An amino acid whenever produced by a process according to any preceding claim.
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE42673L IE42673L (en) | 1976-10-09 |
| IE42673B1 true IE42673B1 (en) | 1980-09-24 |
Family
ID=11192138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE737/76A IE42673B1 (en) | 1975-04-09 | 1976-04-08 | Production of 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 ZA ZA761941A patent/ZA761941B/en unknown
- 1976-03-31 DK DK154676A patent/DK146622C/en not_active IP Right Cessation
- 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 EG EG196/76A patent/EG12543A/en active
- 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
- 1976-04-06 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 LU LU74714A patent/LU74714A1/xx unknown
- 1976-04-07 NO NO761189A patent/NO143901C/en unknown
- 1976-04-07 DD DD192242A patent/DD123599A5/xx unknown
- 1976-04-07 PT PT64983A patent/PT64983B/en unknown
- 1976-04-08 CS CS762334A patent/CS194756B2/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 IN IN611/CAL/76A patent/IN144346B/en unknown
- 1976-04-08 IL IL49372A patent/IL49372A/en unknown
- 1976-04-08 BR BR7602173A patent/BR7602173A/en unknown
- 1976-04-08 HU HU76SA2914A patent/HU176009B/en unknown
- 1976-04-08 PH PH18315A patent/PH12101A/en unknown
- 1976-04-08 YU YU00903/76A patent/YU90376A/en unknown
- 1976-04-08 IE IE737/76A patent/IE42673B1/en unknown
- 1976-04-09 RO RO7685571A patent/RO70427A/en unknown
- 1976-04-09 JP JP51039420A patent/JPS5940823B2/en not_active Expired
- 1976-04-09 SU SU762343157A patent/SU670213A3/en active
- 1976-04-09 NL NL7603816A patent/NL7603816A/en active Search and Examination
- 1976-04-09 DE DE2615594A patent/DE2615594C3/en not_active Expired
- 1976-04-09 AR AR262843A patent/AR217052A1/en active
- 1976-04-09 PL PL1976188626A patent/PL104015B1/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 SE SE7604237A patent/SE409701B/en unknown
-
1979
- 1979-12-30 MY MY100/79A patent/MY7900100A/en unknown
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