DE2615594A1 - PROCESS FOR THE PRODUCTION OF AMINO ACIDS - Google Patents
PROCESS FOR THE PRODUCTION OF AMINO ACIDSInfo
- Publication number
- DE2615594A1 DE2615594A1 DE19762615594 DE2615594A DE2615594A1 DE 2615594 A1 DE2615594 A1 DE 2615594A1 DE 19762615594 DE19762615594 DE 19762615594 DE 2615594 A DE2615594 A DE 2615594A DE 2615594 A1 DE2615594 A1 DE 2615594A1
- Authority
- DE
- Germany
- Prior art keywords
- amino acids
- acid
- preparation
- carbamyl
- acids according
- 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.)
- Granted
Links
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
2 61 5 5 9 A2 61 5 5 9 A
Dr. F. Zumstein sen. - Dr. E. Assmann - Dr. R. Koenigsberger Dipl.-Phys. R. Holzbauer - Dipl.-Ing. F. Klingseisen - Dr. F. Zumstein jun.Dr. F. Zumstein Sr. - Dr. E. Assmann - Dr. R. Koenigsberger Dipl.-Phys. R. Holzbauer - Dipl.-Ing. F. Klingseisen - Dr. F. Zumstein jun.
PATENTANWÄLTEPATENT LAWYERS
B MÜNCHEN Z, B MUNICH Z,
TEUEFON: SAMMEL-NR. 225341 TELEGRAMME: ZUMPAT TELEX 529979TEUEFON: COLLECTION NO. 225341 TELEGRAMS: ZUMPAT TELEX 529979
Case 841 i4/hüCase 841 i4 / hü
SNAMPROGETTI SpA., Mailand/Italien Verfahren zur Herstellung von Aminosäuren.SNAMPROGETTI SpA., Milan / Italy Process for the production of amino acids.
Die Erfindung betrifft ein Verfahren zur Herstellung von Aminosäuren, ausgehend von den entsprechenden Carbamylderivaten.The invention relates to a method for the production of amino acids, starting from the corresponding carbamyl derivatives.
Es ist bekannt, daß optisch aktive Carbamylderivate von Aminosäuren aus den entsprechenden racemischen Hydantoinen durch stereo-selektive enzymatische Hydrolyse gemäß der DT-OS 24 22 erhalten werden können.It is known that optically active carbamyl derivatives of amino acids from the corresponding racemic hydantoins by stereoselective enzymatic hydrolysis according to DT-OS 24 22 can be obtained.
Das auf diese Weise erhaltene Carbamylderivat wurde anschließend in die entsprechende Aminosäure durch bloßes Sieden in wäßriger Lösung übergeführt.The carbamyl derivative thus obtained was then converted into the corresponding amino acid by simple boiling in aqueous solution.
Jedoch war die Hydrolyse des Carbamylderivats in die Aminosäure, die unter derartigen Bedingungen hervorgerufen wurde, sehr langsam, erforderte eine strenge Kontrolle der Arbeitsbedingungen und gab zuweilen Anlass zur Bildung von Nebenprodukten unter Herabsetzung der Ausbeute und sogar unter teilweiser Racemisierung.However, the hydrolysis of the carbamyl derivative into the amino acid produced under such conditions, very slowly, required strict control of the working conditions and sometimes gave rise to the formation of by-products with a reduction in the yield and even with partial racemization.
Es ist ein Ziel der vorliegenden Erfindung, einen neuartigen und einfachen Weg für die Überführung von Carbamy!derivaten in die entsprechenden Aminosäuren zur Verfugung .zu stellen, der unter milden Bedingungen abläuft derart, daß die auf diese Weise gebildete Aminosäure die optische Reinheit der Ausgangscarbamylderivate beibehält.It is an object of the present invention to provide a novel and simple way of converting carbamyl derivatives into the corresponding amino acids are available .zu provide the under mild conditions take place in such a way that the amino acid formed in this way has the optical purity of the starting carbamyl derivatives maintains.
609842/ 1083609842/1083
ORIGINAL INSPECTEDORIGINAL INSPECTED
Das erfindungsgemäße Verfahren umfaßt eine Stufe der Umsetzung des Carbamylderivates mit oxydierenden Substanzen in Gegenwart eines saure Gruppen bzw. Säuregruppen enthaltenden Ionenaus tausche rharzes und dieser Vorgang ist insofern äußerst überraschend, als bisher bekannt war, daß derartige Reaktanten auf die Aminogruppe der Aminosäure unter Bildung der entsprechenden Hydroxysäure einwirken und es dann unmöglich war, das Carbamylderivat in die entsprechende Aminosäure überzuführen, da wie gesagt das letztere sogleich in die Hydroxysäure übergeführt wurde. Im Gegensatz hierzu wurde erfindungsgerpäß gefunden, daß bei einer Arbeitsweise in Gegenwart von kationischen Harzen bei einem geeigneten pH-Wert und bei geeigneten Temperaturbedingungen überraschenderweise hohe Ausbeuten erreicht -werden können, da die Aminosäure von einem Angriff durch die oxydierende Reaktante vollständig ausgenommen ist.The process according to the invention comprises a step of reacting the carbamyl derivative with oxidizing substances in the presence an ion exchange resin containing acid groups or acid groups and this process is extremely surprising, than was previously known that such reactants act on the amino group of the amino acid to form the corresponding Hydroxy acid act and it was then impossible to convert the carbamyl derivative into the corresponding amino acid, as I said the latter was immediately converted into the hydroxy acid. In contrast, it was found according to the invention that in one Operation in the presence of cationic resins at a suitable pH value and under suitable temperature conditions Surprisingly high yields can be achieved because the amino acid is protected from attack by the oxidizing reactant is completely excluded.
Das vorstehende Verfahren wird durchgeführt, indem man das Carbamylderivat oder ein Salz desselben in Wasser bei einer variierbaren Konzentration, vorzugsweise nahe der Sättigung,löst. Die Lösung wird durch eine Menge an kationischem Harz in der Säureform bzw. sauren Form, das eine derartige Austauscherkapazität besitzt, daß 1 bis 5 Mole Produkt gebunden werden, ergänzt. Während dieser Stufe wird der pH erniedrigt und das Carbamylderivat in einer Menge, die dessen Löslichkeit übersteigt, ausgefällt. Es werden 1 bis 1,5 Äquivalente Oxydationsmittel hinzugefügt, wobei die gesamte Stufe bei einer Temperatur im Bereich von 0 bis 40°C durchgeführt wird.The above procedure is carried out by adding the carbamyl derivative or a salt thereof in water at a variable concentration, preferably close to saturation, dissolves. The solution is made up of an amount of cationic resin in the Acid form or acid form, which has such an exchange capacity that 1 to 5 moles of product are bound, added. During this stage the pH is lowered and the carbamyl derivative in an amount that exceeds its solubility, failed. 1 to 1.5 equivalents of oxidizing agent are added, with the entire stage at one temperature is carried out in the range from 0 to 40 ° C.
Als kationische Harze können Harze mit verschiedenen sauren Gruppen bzw. Säuregruppen verwendet werden, obgleich Harze vom Sulfon-bzw. Sulfonsäuretyp bevorzugt verwendet werden. Auch das Oxydationsmittel stellt kein Problem dar, obgleich die Verwendung von salpetriger Säure (nitrous acid) oder eines Salzes derselben bevorzugt ist.As the cationic resins, resins having various acidic groups can be used or acid groups are used, although resins from the sulfone or. Sulfonic acid type are preferably used. That too Oxidizing agents are not a problem, although the use of nitrous acid or a salt thereof is preferred.
Nach Vervollständigung der Reaktion wird die Aminosäure aus dem Harz mit einer Base eluiert, wohingegen das Harz erneut in seine saure Form übergeführt werden kann. Aus dem Eluat wird dieAfter completion of the reaction, the amino acid is eluted from the resin with a base, whereas the resin is again in its acidic form can be converted. The eluate becomes the
609842/1083609842/1083
Aminosäure durch einfache Konzentrierungs- und Kristallisationsverfahren gewonnen.Amino acid through simple concentration and crystallization processes won.
Die vorstehend erläuterte Verfahrensweise und weitere Einzelheiten werden anhand der folgenden Beispiele näher veranschaulicht .The procedure outlined above and other details are illustrated in more detail using the following examples.
50 ml einer 25 mM-Lösung von N-Carbamyl-a-alanin werden bei 0°C mit 5 ml einer 50 mM-Lösung von NaNOp in Wasser behandelt. Man mißt gelegentlich die Konzentration der Aminosäure in der Lösung. Die Konzentration nimmt langsam ab, nachdem in der ersten Stunde der Umsetzung ein Maximum von 5 mM erreicht worden war und fällt nach 5 Stdn. auf 3,2 mM.50 ml of a 25 mM solution of N-carbamyl-a-alanine are added to 0 ° C treated with 5 ml of a 50 mM solution of NaNOp in water. Occasionally one measures the concentration of the amino acid in the Solution. The concentration slowly decreases after reaching a maximum of 5 mM in the first hour of the reaction and falls to 3.2 mM after 5 hours.
Die chromatographische Analyse der Mischung zeigt die Anwesenheit einer beträchtlichen Menge an Milchsäure.Chromatographic analysis of the mixture shows the presence of a significant amount of lactic acid.
Man schlämmte 194 g (1 Mol) D-N-Carbamyl-phenylglyein mit einer optischen Reinheit von 99 % in 10 1 entionisiertem Wasser in Gegenwart von 8 1 Amberlite I.R. 120 (H+) (Kationenaustauseher mit vernetztem Polystyrolgerüst mit -S02-0H-Gruppen) auf. Unter Weiterrühren der Lösung bei Raumtemperatur fügte man 83 g (1,2 Mol) Natriumnitrit hinzu. Nach ca. 2 Stdn. wurde das Harz abfiltriert, zweimal mit 10 1 entmineralisiertem Wasser gewaschen und dann auf eine Säule (Durchmesser 11 cm, Höhe 1 m) übergeführt. Das Harz wurde dann mit 2 M Ammoniak eluiert: Die Aminosäure liegt in ihrer Gesamtheit in der Fraktion von 10 bis 15 1 Eluat vor.194 g (1 mol) of DN-carbamyl-phenylglyein with an optical purity of 99 % were slurried in 10 l of deionized water in the presence of 8 l of Amberlite IR 120 (H + ) (cation exchanger with crosslinked polystyrene structure with -S0 2 -0H groups ) on. While stirring the solution further at room temperature, 83 g (1.2 mol) of sodium nitrite were added. After about 2 hours, the resin was filtered off, washed twice with 10 l of demineralized water and then transferred to a column (diameter 11 cm, height 1 m). The resin was then eluted with 2 M ammonia: the amino acid is present in its entirety in the fraction of 10 to 15 l of eluate.
Die Lösung des Ammoniumsalzes des D-Phenylglycins ( 5 1 ) wird unter vermindertem Druck zur Trockne eingedampft. Es werden 150 g (99 % d.Th.) D(-)-Phenylglyein mit einem Wert für °The solution of the ammonium salt of D-phenylglycine (5 l) is evaporated to dryness under reduced pressure. There are 150 g (99 % of theory) D (-) - phenylglyein with a value for °
von 157° (c = 0,5; HCl 1 N), d.h. einer optischen Reinheit von mehr als 98 fo, wenn man für den [etI^ -Wert die Daten der technischen Literatur (Org. Synth., 22, 23, 19^2) zugrunde legt, erhalten. 60984^/1083of 157 ° (c = 0.5; HCl 1 N), ie an optical purity of more than 98 fo, if the data of the technical literature (Org. Synth., 22, 23, 19 ^ 2) is based on received. 60984 ^ / 1083
Indem man die in Beispiel 2 angegebene Verfahrensweise befolgt und von 132 g (1 Mol) L-N-Carbamyl-a-alanin mit einer optischen Reinheit von 98 % ausgeht, werden 87 g (0,98 Mol) L-a-Alanin mit einem Wert für [α]20von +14,5° ( c = 2; HCl 1N) (Literaturwert für [a]p5= +14,7, J- Chem.Soc, JM3, 526, 1918) erhalten.By following the procedure given in Example 2 and starting from 132 g (1 mol) of LN-carbamyl-a-alanine with an optical purity of 98 % , 87 g (0.98 mol) of La-alanine with a value for [ α] 20 of + 14.5 ° (c = 2; HCl 1N) (literature value for [a] p 5 = +14.7, J-Chem. Soc, JM3, 526, 1918).
Indem man das Verfahren der Beispiele 2 und 3 befolgt und von 16O g (1 Mol) L-N-Carbamyl-valin mit einer optischen i Reinheit von 97 % ausgeht, erhält man 110 g (0,94 Mol) L-Valin; [α]20= 28,2° (c = 3; HGl 6N), Literaturwert für [α]20= 28,8° (Ber., 39, 2320, 1906).By following the procedure of Examples 2 and 3 and starting with 160 g (1 mole) of LN-carbamylvaline having an optical purity of 97 % , 110 g (0.94 moles) of L-valine are obtained; [α] 20 = 28.2 ° (c = 3; HGl 6N), literature value for [α] 20 = 28.8 ° (Ber., 39, 2320, 1906).
Indem man die Verfahrensweise der Beispiele 2 und 4 befolgt und von 192 g (1 Mol) L-N-Carbamyl-methionin mit einer hohen optischen Reinheit von 99 % ausgeht, erhält man 145 g ,By following the procedure of Examples 2 and 4 and starting from 192 g (1 mol) of LN-carbamyl-methionine with a high optical purity of 99 % , 145 g are obtained,
(0,97 Mol) L-Methionin; [a]^5= -8,01° (c « 0,8, Wasser) jL-methionine (0.97 moles); [a] ^ 5 = -8.01 ° (c «0.8, water) j
(Literaturwert für [a]D = -8,11°; J. Am.Chera.Soc, 53, 3490,1931). ΐ(Literature value for [a] D = -8.11 °; J. Am.Chera.Soc, 53, 3490, 1931). ΐ
Indem man die in den Beispielen 2 und 4 beschriebenen Verfahrensweisen befolgt und von 190 g (1 Mol) L-N-Carbamylglutaminsäure mit einer optischen Reinheit von 98 % ausgeht, erhält man 183 g (0,96 Mol) L-Glutaminsäure; [a]50= (c = 1; HCl 6N) (Literaturwert für [ccJ^2= +31,2°; Ber., 40, 3717, 1907).By following the procedures described in Examples 2 and 4 and starting from 190 g (1 mol) of LN-carbamylglutamic acid with an optical purity of 98 % , 183 g (0.96 mol) of L-glutamic acid are obtained; [a] 0 = 5 (c = 1; HCl 6N) (literature value for [CCJ ^ 2 = + 31.2 °; Ber, 40, 3717 1907.).
609842/1083609842/1083
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 (3)
| Publication Number | Publication Date |
|---|---|
| DE2615594A1 true DE2615594A1 (en) | 1976-10-14 |
| DE2615594B2 DE2615594B2 (en) | 1978-07-20 |
| DE2615594C3 DE2615594C3 (en) | 1979-03-15 |
Family
ID=11192138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2615594A Expired DE2615594C3 (en) | 1975-04-09 | 1976-04-09 | Process for the preparation of aminocarboxylic 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) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0288795A2 (en) * | 1987-04-28 | 1988-11-02 | ENIRICERCHE S.p.A. | Method of preparation of optically active alpha-amino-acids |
| US5777076A (en) * | 1994-10-24 | 1998-07-07 | Universite Montpellier Ii Sciences Et Techniques Du Languedoc | Method for peptide synthesis starting from N- (N'-nitrosocarbamoyl) amino acids |
| 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 |
| US6280979B1 (en) * | 1997-03-31 | 2001-08-28 | Council Of Scientific & Industrial Research | Microbial process for the production of D(-)-N-carbamoylphenylglycine |
Families Citing this family (2)
| 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 |
| CN105601542B (en) * | 2016-01-08 | 2017-10-24 | 南京工业大学 | A kind of method that nitration mixture crystallizes N carbamylglutamic acids |
-
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 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 DD DD192242A patent/DD123599A5/xx unknown
- 1976-04-07 LU LU74714A patent/LU74714A1/xx unknown
- 1976-04-07 PT PT64983A patent/PT64983B/en unknown
- 1976-04-07 FR FR7610087A patent/FR2306976A1/en active Granted
- 1976-04-07 NO NO761189A patent/NO143901C/en unknown
- 1976-04-08 IL IL49372A patent/IL49372A/en unknown
- 1976-04-08 BR BR7602173A patent/BR7602173A/en unknown
- 1976-04-08 AT AT258276A patent/AT343092B/en not_active IP Right Cessation
- 1976-04-08 PH PH18315A patent/PH12101A/en unknown
- 1976-04-08 IN IN611/CAL/76A patent/IN144346B/en unknown
- 1976-04-08 CS CS762334A patent/CS194756B2/en unknown
- 1976-04-08 HU HU76SA2914A patent/HU176009B/en unknown
- 1976-04-08 IE IE737/76A patent/IE42673B1/en unknown
- 1976-04-08 YU YU00903/76A patent/YU90376A/en unknown
- 1976-04-08 BE BE165963A patent/BE840527A/en not_active IP Right Cessation
- 1976-04-09 ES ES447176A patent/ES447176A1/en not_active Expired
- 1976-04-09 DE DE2615594A patent/DE2615594C3/en not_active Expired
- 1976-04-09 RO RO7685571A patent/RO70427A/en unknown
- 1976-04-09 NL NL7603816A patent/NL7603816A/en active Search and Examination
- 1976-04-09 PL PL1976188626A patent/PL104015B1/en unknown
- 1976-04-09 JP JP51039420A patent/JPS5940823B2/en not_active Expired
- 1976-04-09 SE SE7604237A patent/SE409701B/en unknown
- 1976-04-09 MX MX000157U patent/MX3304E/en unknown
- 1976-04-09 SU SU762343157A patent/SU670213A3/en active
- 1976-04-09 BG BG7600032860A patent/BG24664A3/en unknown
- 1976-04-09 AR AR262843A patent/AR217052A1/en active
-
1979
- 1979-12-30 MY MY100/79A patent/MY7900100A/en unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0288795A2 (en) * | 1987-04-28 | 1988-11-02 | ENIRICERCHE S.p.A. | Method of preparation of optically active alpha-amino-acids |
| EP0288795A3 (en) * | 1987-04-28 | 1989-09-06 | Eniricerche S.P.A. | Method of preparation of optically active alpha-amino-acids |
| US4925978A (en) * | 1987-04-28 | 1990-05-15 | Eniricerche S.P.A. | Method of preparation of optically active alpha-amino-acids |
| US5777076A (en) * | 1994-10-24 | 1998-07-07 | Universite Montpellier Ii Sciences Et Techniques Du Languedoc | Method for peptide synthesis starting from N- (N'-nitrosocarbamoyl) amino acids |
| 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 |
| US6280979B1 (en) * | 1997-03-31 | 2001-08-28 | Council Of Scientific & Industrial Research | Microbial process for the production of D(-)-N-carbamoylphenylglycine |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2526594C2 (en) | Process for the production of L-phenylglycine and for the recovery of D-phenylglycine amide | |
| DE112008001983B4 (en) | Process for the synthesis of Na-beta-alaninate | |
| DE3229674C2 (en) | ||
| DE2422737A1 (en) | PROCESS FOR THE PREPARATION OF L-CARBAMYLAMINO ACIDS AND THE CORRESPONDING L-AMINO ACIDS | |
| DE2615594A1 (en) | PROCESS FOR THE PRODUCTION OF AMINO ACIDS | |
| DE2501957C2 (en) | Process for the production of optically active p-hydroxyphenylglycine | |
| DE3538746C2 (en) | ||
| EP0664796B1 (en) | Method of preparing aminoalkylhydantoins and aminoalkyl-alpha-aminoacids | |
| DE4119029C2 (en) | ||
| DE2813712A1 (en) | PROCESS FOR SEPARATION OF RACEMIC ALPHA-AMINONITRILE | |
| DE3719872A1 (en) | METHOD FOR PRODUCING D-ALANINE FROM L-CHLORINE PROPIONIC ACID | |
| DE4025962A1 (en) | Pantolactone and beta-alanine prodn. from pantothenic acid solns. - esp. mother liquor from calcium D-pantothenate mfr., by treatment with acidic cation exchanger at elevated temp. | |
| DE2350610A1 (en) | METHOD OF MANUFACTURING THE OPTICAL ANTIPODES OF PANTOLAKTON | |
| EP0184732A2 (en) | Use of N-maleinyl phenylalanine alkyl esters and process for their preparation | |
| DE1145176B (en) | Process for the preparation of d, l-methionine by hydrolysis of ª ‡ -amino-ª † -methylmercaptobutyronitrile | |
| DE2925359C3 (en) | Process for the preparation of salts of (-) cis-1,2-epoxypropylphosphonic acid | |
| AT225183B (en) | Process for the preparation of phenylalanine derivatives | |
| EP0759475A1 (en) | Method for the production of (R)-ter-leucine | |
| DE1111187B (en) | Process for the preparation of phosphoric acid esters, phosphoric amides or carbonic anhydrides | |
| DE2558507B2 (en) | Process for the resolution of dJ-1-phenyl-2-amino-2-propanol | |
| DE2227504C3 (en) | Process for the preparation of trans-4-aminomethylcyclohexane-i-carboxylic acid or its salts | |
| CH643528A5 (en) | METHOD FOR PRODUCING BETA CHLORALANINE. | |
| DE1155137B (en) | Process for the production of L-glutamic acid from racemic glutamic acid | |
| DE1593832B2 (en) | PROCESS FOR THE MANUFACTURING OF CALCIUM-DL-PANTOTHENATE | |
| DE1954519A1 (en) | Vitamin b, active o-arylthiaminedisulphides - selective preparation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |