CS202445B1 - Process for producing l-phenylalanine and l-asparagic acid from mother liquor after crystallization of hydrochloride of l-aspartyl-l-phenylalanine methylestere - Google Patents
Process for producing l-phenylalanine and l-asparagic acid from mother liquor after crystallization of hydrochloride of l-aspartyl-l-phenylalanine methylestere Download PDFInfo
- Publication number
- CS202445B1 CS202445B1 CS86479A CS86479A CS202445B1 CS 202445 B1 CS202445 B1 CS 202445B1 CS 86479 A CS86479 A CS 86479A CS 86479 A CS86479 A CS 86479A CS 202445 B1 CS202445 B1 CS 202445B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenylalanine
- crystallization
- hydrochloride
- mother liquors
- aspartyl
- Prior art date
Links
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 title claims description 18
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 title claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 10
- 238000002425 crystallisation Methods 0.000 title claims description 10
- 230000008025 crystallization Effects 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 9
- 229960005190 phenylalanine Drugs 0.000 title claims description 9
- YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 title claims description 3
- 239000012452 mother liquor Substances 0.000 title description 3
- 229960005261 aspartic acid Drugs 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims description 10
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- ZAIZDXVMSSDZFA-QRPNPIFTSA-N (2s)-2-amino-3-phenylpropanoic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CC1=CC=CC=C1 ZAIZDXVMSSDZFA-QRPNPIFTSA-N 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000011156 evaluation Methods 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- AAQFSZFQCXLMNT-ACMTZBLWSA-N (3s)-3-amino-4-[[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid;hydrochloride Chemical compound Cl.OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 AAQFSZFQCXLMNT-ACMTZBLWSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000003599 food sweetener Nutrition 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 239000003765 sweetening agent Substances 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Peptides Or Proteins (AREA)
Description
(54) Způsob získávání L-fenylalaninu a kyseliny L-asparagové z matečných louhů po krystalizaci hydrochloridu methylesteru L-aspartyl-L-fenylalaninu(54) A process for obtaining L-phenylalanine and L-aspartic acid from mother liquors after crystallization of L-aspartyl-L-phenylalanine methyl ester hydrochloride
Vynález se týká způsobu získávání L-fenylalaninu a kyseliny L-asparagové z matečných louhů po krystalizaci hydrochloridu methylesteru L-aspartyl-L-fenylalaninu.The invention relates to a process for obtaining L-phenylalanine and L-aspartic acid from mother liquors after crystallization of L-aspartyl-L-phenylalanine methyl ester hydrochloride.
Při syntéze peptidického sladidla hydrochloridu methylesteru L-aspartyl-L-fenylalaninu zůstává po jeho krystalizaci, výhodně z acetonu (čs. autorské osvědčení č. 187 199), v matečném louhu řada vedlejších produktů spolu s neizolovatelným množstvím žádané látky, které již není možno ekonomicky získat. Protože aminokyseliny L-fenylalanin a kyselina L-asparagová jsou nejdražšími výchozími látkami pro syntézu tohoto sladidla, je nalezení vhodného způsobu jejich regenerace a možnosti vrácení do výrobního procesu z hlediska ekonomizace výroby velmi důležité.In the synthesis of the peptide sweetener L-aspartyl-L-phenylalanine hydrochloride hydrochloride, after crystallization, preferably from acetone (cf. No. 187 199), a number of byproducts remain in the mother liquor together with a non-recoverable amount of the desired substance which is no longer economically possible gain. Since the amino acids L-phenylalanine and L-aspartic acid are the most expensive starting materials for the synthesis of this sweetener, finding a suitable method for their regeneration and the possibility of returning to the production process is very important in terms of economizing production.
Řešení tohoto úkolu je předmětem způsobu získávání L-fenylalaninu a kyseliny L-asparagové z matečných louhů po krystalizaci hydrochloridu methylesteru L-aspartyl-L-fenylalaninu zbavených acetonu, podle vynálezu, jehož podstata spočívá v tom, že se matečné louhy hydrolýzují minerální kyselinou, s výhodou 20 až 36 °/o kyselinou chlorovodíkovou, při teplotě 50 až 100 °C, po skončené hydrolýze se ochlazením na 10 až 20 °C vyloučený hydrochlorid L-fenylalaninu izoluje, matečné louhy se odpaří k suchu a z odparku se po< rozpuštění ve vodě a po úpravě pH na hodnotu 2,5 až 3,5 izoluje krystalizací kyselina L-asparagová.The object of the present invention is to provide a process for obtaining L-phenylalanine and L-aspartic acid from mother liquors after crystallization of L-aspartyl-L-phenylalanine methyl ester hydrochloride deprived of acetone according to the invention, characterized in that the mother liquors are hydrolyzed with mineral acid. preferably from 20 to 36 ° C with hydrochloric acid, at a temperature of 50 to 100 ° C, after complete hydrolysis, the precipitated L-phenylalanine hydrochloride is isolated by cooling to 10 to 20 ° C, the mother liquors are evaporated to dryness and the residue is dissolved in water and after adjusting the pH to 2.5 to 3.5, L-aspartic acid is isolated by crystallization.
Popsaným způsobem se všechny látky peptidického charakteru, které jsou obsaženy ve výchozím matečném louhu, převedou na L-fenylalanin a kyselinu L-asparagovou. Po hydrolýze se získá kolem 80 % teorie L-fenylalaninu a z odparku matečných louhů po úpravě pH kolem 60 % teorie kyseliny L-asparagové. Významnou výhodou způsobu podle vynálezu je také ta skutečnost, že získané aminokyseliny jsou po jednom překrystalování z vhodného rozpouštědla (L-fenylalanin ze zředěné kyseliny chlorovodíkové a kyselina asparagová z vody) dostatečně čisté pro opětné použití k syntéze výše jmenovaného peptidického sladidla.As described above, all peptides of the parent mother liquor are converted to L-phenylalanine and L-aspartic acid. After hydrolysis, about 80% of the theory of L-phenylalanine is obtained, and from the evaporation of the mother liquors after adjustment of the pH about 60% of the theory of L-aspartic acid. An important advantage of the process of the invention is also that the obtained amino acids are sufficiently pure for reuse to synthesize the aforementioned peptide sweetener after one recrystallization from a suitable solvent (L-phenylalanine from dilute hydrochloric acid and aspartic acid from water).
Bližší podrobnosti způsobu podle vynálezu jsou patrné z následujících příkladů provedení, které tentoi způsob pouze ilustrují, ale nijak neomezují:Further details of the method according to the invention can be seen from the following examples, which are illustrative but not limiting:
Příklad 1Example 1
Ze 3 litrů matečných louhů po krystalizaci hydrochloridu methylesteru L-aspartýl-Lfenylalaninu se oddestiluje aceton. Přidá se 0,7 litru konc. kyseliny chlorovodíkové a reakční směs se zahřívá na 90 až 100 °C po dobu 15 hodin. Potom se reakční směs zfiltruje přes aktivní uhlí a nechá vychladnout (na 10 až 20 °C). Vyloučený hydrochlorid L-fenylalaninu se odsaje a překrystaluje ze zředěné kyseliny chlorovodíkové. Výtěžek 260 g, tj. 80 % teorie.Acetone was distilled off from 3 liters of mother liquors after crystallization of L-aspartyl-L-phenylalanine methyl ester hydrochloride. 0.7 liters of conc. hydrochloric acid and the reaction mixture is heated at 90-100 ° C for 15 hours. The reaction mixture was then filtered through charcoal and allowed to cool (to 10-20 ° C). The precipitated L-phenylalanine hydrochloride is filtered off with suction and recrystallized from dilute hydrochloric acid. Yield: 260 g, i.e. 80% of theory.
Hodnota (a) g = — 15° + 1° (voda) je shodná s autentickým preparátem; látka je podle elektrořoretického hodnocení čistá.(A) g = - 15 ° + 1 ° (water) is identical to the authentic formulation; the substance is pure according to electro-theoretical evaluation.
Matečné louhy po» oddělení hydrochloridu L-fenylalaninu se odpaří k suchu a odparek se rozpustí v 700 ml vody. Roztokem hydroxidu sodného se upraví pH na hodnotu 3, ochlazením vyloučená kyselina L-asparagová se odsaje a promyje směsí ethanol-vodaThe mother liquors of L-phenylalanine hydrochloride were evaporated to dryness and the residue was dissolved in 700 ml of water. The pH is adjusted to 3 with sodium hydroxide solution, the precipitated L-aspartic acid precipitated is suction filtered and washed with ethanol-water.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS86479A CS202445B1 (en) | 1979-02-07 | 1979-02-07 | Process for producing l-phenylalanine and l-asparagic acid from mother liquor after crystallization of hydrochloride of l-aspartyl-l-phenylalanine methylestere |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS86479A CS202445B1 (en) | 1979-02-07 | 1979-02-07 | Process for producing l-phenylalanine and l-asparagic acid from mother liquor after crystallization of hydrochloride of l-aspartyl-l-phenylalanine methylestere |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS202445B1 true CS202445B1 (en) | 1981-01-30 |
Family
ID=5341624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS86479A CS202445B1 (en) | 1979-02-07 | 1979-02-07 | Process for producing l-phenylalanine and l-asparagic acid from mother liquor after crystallization of hydrochloride of l-aspartyl-l-phenylalanine methylestere |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS202445B1 (en) |
-
1979
- 1979-02-07 CS CS86479A patent/CS202445B1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0543717B2 (en) | ||
| JPS5935381B2 (en) | Method for resolving (+)- and (-)-6-methoxy-α-methyl-2-naphthaleneacetic acid | |
| US3733352A (en) | Preparation of d-threo-1-p-methyl-sulfonylphenyl-2-dichloro-acet-amidopropane-1,3-diol | |
| US3032585A (en) | Process for the production of p-bis-(2-chloroethyl)-aminophenylalanine | |
| US3832388A (en) | Resolution of 2-(p-hydroxy)phenylglycine | |
| JPH04234374A (en) | Production of diketopiperazine derivative | |
| US6197998B1 (en) | Process for producing N-glycyltyrosine and its crystal structure | |
| US3340298A (en) | Phenylalkanolamine derivatives | |
| CS202445B1 (en) | Process for producing l-phenylalanine and l-asparagic acid from mother liquor after crystallization of hydrochloride of l-aspartyl-l-phenylalanine methylestere | |
| Coutsogeorgopoulos et al. | On β-D-Glucosylamides of L-Amino Acids and of Nicotinic Acid | |
| US2994692A (en) | Process of preparing nu-trityl peptides | |
| US2991307A (en) | Process of resolving nu, nu-dibenzyl-dl-alpha-amino acids and products | |
| SU489310A3 (en) | The method of obtaining the derivative of biphenylacetamide or its salt | |
| US2813876A (en) | Resolution of tryptophane derivatives | |
| SE459176B (en) | ASPARTAME SYNTHESIS | |
| PT91145B (en) | PROCESS FOR THE SYNTHESIS OF OPTICALLY ACTIVE AMINO ACIDS | |
| JP2971291B2 (en) | Production method of optically active 2-aminobutyric acid | |
| US2921959A (en) | Process of resolving dl-serine | |
| US2719849A (en) | beta-(1, 2, 4-triazolyl-3)-alanine and its salts and the preparation thereof | |
| RU1836334C (en) | Method for obtaining methyl ether of 3-aminocrotonic acid | |
| US4226803A (en) | Process for production of optically active bases | |
| SU408546A1 (en) | The method of obtaining hydrochloride 1 = aminoadamantana | |
| KR20010079913A (en) | METHOD FOR PRODUCING (-)-α-(DIFLUOROMETHYL)ORNITHINE-MONOHYDROCHLORIDE MONOHYDRATE | |
| US2463939A (en) | Phenylacetyl amino acid esters | |
| JPS6259274A (en) | Method for producing optically active phenylserine derivatives |