DE2421291C2 - Verfahren zur optischen Spaltung von DL-Lysin-(p-aminobenzolsulfonat) - Google Patents
Verfahren zur optischen Spaltung von DL-Lysin-(p-aminobenzolsulfonat)Info
- Publication number
- DE2421291C2 DE2421291C2 DE2421291A DE2421291A DE2421291C2 DE 2421291 C2 DE2421291 C2 DE 2421291C2 DE 2421291 A DE2421291 A DE 2421291A DE 2421291 A DE2421291 A DE 2421291A DE 2421291 C2 DE2421291 C2 DE 2421291C2
- Authority
- DE
- Germany
- Prior art keywords
- lysine
- solution
- supersaturated
- aminobenzene sulfonate
- sulfonate
- 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
- 230000003287 optical effect Effects 0.000 title claims description 16
- 238000003776 cleavage reaction Methods 0.000 title claims description 14
- 230000007017 scission Effects 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 11
- OXDWBEVSRWRLEZ-UHFFFAOYSA-N 4-aminobenzenesulfonic acid;2,6-diaminohexanoic acid Chemical compound NCCCCC(N)C(O)=O.NC1=CC=C(S(O)(=O)=O)C=C1 OXDWBEVSRWRLEZ-UHFFFAOYSA-N 0.000 title description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 51
- 239000013078 crystal Substances 0.000 claims description 15
- 238000010956 selective crystallization Methods 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- -1 DL-lysine acetate DL-lysine carbonate Chemical compound 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 54
- 239000004472 Lysine Substances 0.000 description 45
- 229960003646 lysine Drugs 0.000 description 45
- 235000018977 lysine Nutrition 0.000 description 35
- 239000000243 solution Substances 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HVBSAKJJOYLTQU-UHFFFAOYSA-M 4-aminobenzenesulfonate Chemical compound NC1=CC=C(S([O-])(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-M 0.000 description 20
- OXDWBEVSRWRLEZ-JEDNCBNOSA-N 4-aminobenzenesulfonic acid;(2s)-2,6-diaminohexanoic acid Chemical compound NCCCC[C@H](N)C(O)=O.NC1=CC=C(S(O)(=O)=O)C=C1 OXDWBEVSRWRLEZ-JEDNCBNOSA-N 0.000 description 18
- 235000019766 L-Lysine Nutrition 0.000 description 10
- 239000007787 solid Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010899 nucleation Methods 0.000 description 4
- 229950000244 sulfanilic acid Drugs 0.000 description 4
- RRNJROHIFSLGRA-JEDNCBNOSA-N acetic acid;(2s)-2,6-diaminohexanoic acid Chemical compound CC(O)=O.NCCCC[C@H](N)C(O)=O RRNJROHIFSLGRA-JEDNCBNOSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229960002449 glycine Drugs 0.000 description 3
- 229960005357 lysine acetate Drugs 0.000 description 3
- 230000006911 nucleation Effects 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- OCHFNTLZOZPXFE-JEDNCBNOSA-N carbonic acid;(2s)-2,6-diaminohexanoic acid Chemical compound OC(O)=O.NCCCC[C@H](N)C(O)=O OCHFNTLZOZPXFE-JEDNCBNOSA-N 0.000 description 2
- OCHFNTLZOZPXFE-UHFFFAOYSA-N carbonic acid;2,6-diaminohexanoic acid Chemical compound OC(O)=O.NCCCCC(N)C(O)=O OCHFNTLZOZPXFE-UHFFFAOYSA-N 0.000 description 2
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- NEDCLUPMYCVKFO-UHFFFAOYSA-N azanium;4-aminobenzenesulfonate Chemical compound [NH4+].NC1=CC=C(S([O-])(=O)=O)C=C1 NEDCLUPMYCVKFO-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7306318,A NL175617C (nl) | 1973-05-07 | 1973-05-07 | Werkwijze voor de optische splitsing van racemisch lysinesulfanilaat. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2421291A1 DE2421291A1 (de) | 1974-11-28 |
| DE2421291C2 true DE2421291C2 (de) | 1983-02-03 |
Family
ID=19818807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2421291A Expired DE2421291C2 (de) | 1973-05-07 | 1974-05-02 | Verfahren zur optischen Spaltung von DL-Lysin-(p-aminobenzolsulfonat) |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3932491A (OSRAM) |
| AR (1) | AR199434A1 (OSRAM) |
| AT (1) | AT330742B (OSRAM) |
| BE (1) | BE814633A (OSRAM) |
| BR (1) | BR7403691D0 (OSRAM) |
| CH (1) | CH593216A5 (OSRAM) |
| CS (1) | CS176277B2 (OSRAM) |
| DD (1) | DD114062A5 (OSRAM) |
| DE (1) | DE2421291C2 (OSRAM) |
| DK (1) | DK140008B (OSRAM) |
| FR (1) | FR2228745B1 (OSRAM) |
| GB (1) | GB1461836A (OSRAM) |
| HU (1) | HU168550B (OSRAM) |
| IL (1) | IL44763A (OSRAM) |
| IT (1) | IT1011400B (OSRAM) |
| NL (1) | NL175617C (OSRAM) |
| PL (1) | PL89838B1 (OSRAM) |
| RO (1) | RO65810A (OSRAM) |
| SE (1) | SE413403B (OSRAM) |
| SU (1) | SU495827A3 (OSRAM) |
| ZA (1) | ZA742738B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4362959B2 (ja) * | 2000-08-24 | 2009-11-11 | 味の素株式会社 | 塩基性アミノ酸の製造方法 |
| CN102070477B (zh) * | 2010-12-23 | 2014-11-26 | 蚌埠丰原医药科技发展有限公司 | 一种药用级醋酸赖氨酸的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2934561A (en) * | 1955-09-28 | 1960-04-26 | Du Pont | Optically active salts of lysine and butane-2-sulfonic acid |
| US3527776A (en) * | 1966-08-31 | 1970-09-08 | Ajinomoto Kk | Optical resolution of dl-lysine |
| US3925454A (en) * | 1968-04-22 | 1975-12-09 | Tanabe Seiyaku Co | Preparation of optically active isomers of lysines |
| NL6814129A (OSRAM) * | 1968-10-02 | 1970-04-06 | ||
| US3742041A (en) * | 1968-10-04 | 1973-06-26 | Tanabe Seiyaku Co | Process of resolving dl-serine m-xylene-4-sulfonate |
-
1973
- 1973-05-07 NL NLAANVRAGE7306318,A patent/NL175617C/xx not_active IP Right Cessation
-
1974
- 1974-04-08 US US05/459,237 patent/US3932491A/en not_active Expired - Lifetime
- 1974-04-29 GB GB1862174A patent/GB1461836A/en not_active Expired
- 1974-04-30 ZA ZA00742738A patent/ZA742738B/xx unknown
- 1974-05-02 DE DE2421291A patent/DE2421291C2/de not_active Expired
- 1974-05-03 IL IL44763A patent/IL44763A/en unknown
- 1974-05-03 FR FR7415405A patent/FR2228745B1/fr not_active Expired
- 1974-05-05 SU SU2021727A patent/SU495827A3/ru active
- 1974-05-06 CS CS3246A patent/CS176277B2/cs unknown
- 1974-05-06 DD DD178303A patent/DD114062A5/xx unknown
- 1974-05-06 IT IT50810/74A patent/IT1011400B/it active
- 1974-05-06 AR AR253609A patent/AR199434A1/es active
- 1974-05-06 CH CH614774A patent/CH593216A5/xx not_active IP Right Cessation
- 1974-05-06 AT AT372674A patent/AT330742B/de not_active IP Right Cessation
- 1974-05-06 HU HUSA2637A patent/HU168550B/hu unknown
- 1974-05-07 SE SE7406114A patent/SE413403B/xx unknown
- 1974-05-07 RO RO7478701A patent/RO65810A/ro unknown
- 1974-05-07 PL PL1974170884A patent/PL89838B1/pl unknown
- 1974-05-07 BE BE143989A patent/BE814633A/xx not_active IP Right Cessation
- 1974-05-07 BR BR3691/74A patent/BR7403691D0/pt unknown
- 1974-05-07 DK DK248474AA patent/DK140008B/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HU168550B (OSRAM) | 1976-05-28 |
| SU495827A3 (ru) | 1975-12-15 |
| AR199434A1 (es) | 1974-08-30 |
| AT330742B (de) | 1976-07-12 |
| BR7403691D0 (pt) | 1974-12-24 |
| PL89838B1 (OSRAM) | 1976-12-31 |
| FR2228745B1 (OSRAM) | 1977-10-28 |
| US3932491A (en) | 1976-01-13 |
| IL44763A0 (en) | 1974-07-31 |
| NL175617C (nl) | 1984-12-03 |
| RO65810A (fr) | 1979-05-15 |
| NL7306318A (OSRAM) | 1974-11-11 |
| CH593216A5 (OSRAM) | 1977-11-30 |
| IT1011400B (it) | 1977-01-20 |
| BE814633A (fr) | 1974-11-07 |
| SE413403B (sv) | 1980-05-27 |
| DK140008C (OSRAM) | 1979-11-05 |
| FR2228745A1 (OSRAM) | 1974-12-06 |
| IL44763A (en) | 1977-01-31 |
| AU6856174A (en) | 1975-11-06 |
| CS176277B2 (OSRAM) | 1977-06-30 |
| ATA372674A (de) | 1975-10-15 |
| DD114062A5 (OSRAM) | 1975-07-12 |
| GB1461836A (en) | 1977-01-19 |
| DK140008B (da) | 1979-06-05 |
| ZA742738B (en) | 1975-05-28 |
| DE2421291A1 (de) | 1974-11-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2705022B1 (de) | Verfahren zur herstellung eines kristallinen l-mgda-trialkalimetallsalzes | |
| DE2927672C2 (OSRAM) | ||
| EP0312726B1 (de) | Optisch aktive Salze aus einem substituierten Thiazolidin-4-carboxylat und 3-Chlor-2-hydroxypropyltrimethylammonium, deren Herstellung und Verwendung | |
| DE2421291C2 (de) | Verfahren zur optischen Spaltung von DL-Lysin-(p-aminobenzolsulfonat) | |
| DE68921163T2 (de) | Isolierung von L-Phenylalanin aus dessen racemischen Mischungen. | |
| DE2261926B2 (de) | Verfahren zur Herstellung von DL-Methionyl-DL-methionin | |
| DE1949585C3 (de) | Verfahren zur Gewinnung von L-Lysin oder einem Säureadditionssalz davon aus DL-Lysin | |
| DE1814575C3 (de) | Verfahren zur Gewinnung von optisch aktivem Lysin sowie das DL-, D- und L-Lysinphenoxyacetat | |
| DE1695894C3 (de) | Verfahren zur Herstellung von D- und L-Prolin | |
| DE1645977A1 (de) | Verfahren zur Herstellung von Molekularverbindungen von Inosin-Tryptophan | |
| EP0090087B1 (de) | Verfahren zur Gewinnung von S-(Carboxymethyl)-(R)-cystein und S-(Carboxymethyl)-(S)-cystein | |
| DE2612615C2 (de) | Verfahren zur Gewinnung von optisch aktivem α-Phenylglycin und Zwischenprodukte dafür | |
| DE2044680A1 (de) | Verfahren zur Racemisierung von optisch aktivem Ammonium N acetyl alpha aminophenyl acetat | |
| DE1493894A1 (de) | Verfahren zur Herstellung von Ornithinasparaginat | |
| DE2211252A1 (de) | Verfahren zur Auftrennung der Lithiumsalze von DL^-Pyrrolidon-S-carbonsäure in die optisch aktiven Enantiomeren | |
| DE1518033C3 (de) | Verfahren zur Herstellung von L-Arginin-L-asparaginat | |
| DE1518368B1 (de) | Verfahren zur Zerlegung des Ammoniumsalzes des racemichen N-Benzoyl-serin in seine optisch aktiven Komponenten | |
| DE2605567C3 (de) | Verfahren zur Gewinnung von optisch aktivem a Phenylglycin-hydrochlorid | |
| DE2150994A1 (de) | Verfahren zur herstellung von reinen alkalisalzen von aminopolycarbonsaeuren | |
| AT294851B (de) | Verfahren zur Herstellung eines neuen Diastereomeren eines Antipoden der (cis-1,2-Epoxypropyl)-phosphonsäure | |
| DE1593817C3 (de) | Verfahren zur optischen Aufspaltung von Calciumpantothenat | |
| DE1920413C3 (de) | Verfahren zur optischen Spaltung von DL-Lysin | |
| DE1668975C3 (de) | Verfahren zur Erhöhung der optischen Reinheit von optisch aktivem Lysinmonohydrochlorid | |
| DE1618492C (de) | Fruktosegewinnung aus Zucker | |
| DE1090675B (de) | Verfahren zum Spalten eines Gemisches aus Monoammonium-D- und -L-glutamat |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |