SK5499A3 - Process for the preparation of the disodium salt of z-l-aspartic acid from fumaric acid - Google Patents

Process for the preparation of the disodium salt of z-l-aspartic acid from fumaric acid Download PDF

Info

Publication number: SK5499A3
Authority: SK; Slovakia
Prior art keywords: process according; ammonia; solution; fumaric acid; aspartate
Prior art date: 1998-02-02

Application number

SK54-99A

Other languages

English (en)

Slovak (sk)

Inventor

Karl-Heinz Giselbrecht

Walter Raml

Original Assignee

Chemie Linz Gmbh

Priority date (The priority date 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 date listed.)

1998-02-02

Filing date

1999-01-15

Publication date

1999-08-06

1999-01-15 Application filed by Chemie Linz Gmbh filed Critical Chemie Linz Gmbh

1999-08-06 Publication of SK5499A3 publication Critical patent/SK5499A3/sk

Links

VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 title claims abstract description 60
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title claims abstract description 32
239000001530 fumaric acid Substances 0.000 title claims abstract description 30
238000000034 method Methods 0.000 title claims description 24
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 title claims description 18
XYXYXSKSTZAEJW-VIFPVBQESA-N (2s)-2-(phenylmethoxycarbonylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 XYXYXSKSTZAEJW-VIFPVBQESA-N 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 54
229910021529 ammonia Inorganic materials 0.000 claims abstract description 26
108700016171 Aspartate ammonia-lyases Proteins 0.000 claims abstract description 13
244000005700 microbiome Species 0.000 claims abstract description 8
239000012442 inert solvent Substances 0.000 claims abstract description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 48
238000006243 chemical reaction Methods 0.000 claims description 15
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 claims description 13
XMXOIHIZTOVVFB-JIZZDEOASA-L disodium;(2s)-2-aminobutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CC([O-])=O XMXOIHIZTOVVFB-JIZZDEOASA-L 0.000 claims description 10
YEOCBTKAGVNPMO-JIZZDEOASA-N diazanium;(2s)-2-aminobutanedioate Chemical compound [NH4+].[NH4+].[O-]C(=O)[C@@H](N)CC([O-])=O YEOCBTKAGVNPMO-JIZZDEOASA-N 0.000 claims description 8
238000006911 enzymatic reaction Methods 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
239000008346 aqueous phase Substances 0.000 claims description 6
239000000725 suspension Substances 0.000 claims description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
108010011485 Aspartame Proteins 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
239000000605 aspartame Substances 0.000 claims description 3
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 3
229960003438 aspartame Drugs 0.000 claims description 3
235000010357 aspartame Nutrition 0.000 claims description 3
239000010409 thin film Substances 0.000 claims description 3
238000001944 continuous distillation Methods 0.000 claims description 2
230000002255 enzymatic effect Effects 0.000 claims description 2
239000010408 film Substances 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
238000005191 phase separation Methods 0.000 claims description 2
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 2
COLNVLDHVKWLRT-QMMMGPOBSA-N phenylalanine group Chemical group N[C@@H](CC1=CC=CC=C1)C(=O)O COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 2
239000003799 water insoluble solvent Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 abstract description 5
150000001875 compounds Chemical class 0.000 abstract 1
239000000243 solution Substances 0.000 description 35
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 10
229960005261 aspartic acid Drugs 0.000 description 8
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 7
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 7
108090000790 Enzymes Proteins 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical group CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000012266 salt solution Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical group CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 2
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
-1 ammonium ions Chemical class 0.000 description 2
229960001230 asparagine Drugs 0.000 description 2
235000009582 asparagine Nutrition 0.000 description 2
235000003704 aspartic acid Nutrition 0.000 description 2
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 2
230000000694 effects Effects 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
239000001630 malic acid Substances 0.000 description 2
235000011090 malic acid Nutrition 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000010802 sludge Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000002351 wastewater Substances 0.000 description 2
241001550224 Apha Species 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000588915 Klebsiella aerogenes Species 0.000 description 1
241000191936 Micrococcus sp. Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
241000589540 Pseudomonas fluorescens Species 0.000 description 1
241000607715 Serratia marcescens Species 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000008122 artificial sweetener Substances 0.000 description 1
235000021311 artificial sweeteners Nutrition 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000003795 desorption Methods 0.000 description 1
SVABQOITNJTVNJ-UHFFFAOYSA-N diphenyl-2-pyridylphosphine Chemical compound C1=CC=CC=C1P(C=1N=CC=CC=1)C1=CC=CC=C1 SVABQOITNJTVNJ-UHFFFAOYSA-N 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
230000004992 fission Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/20—Aspartic acid; Asparagine

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Microbiology (AREA)
General Chemical & Material Sciences (AREA)
Biotechnology (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

SK54-99A 1998-02-02 1999-01-15 Process for the preparation of the disodium salt of z-l-aspartic acid from fumaric acid SK5499A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT0016398A ATA16398A (de)	1998-02-02	1998-02-02	Verfahren zur herstellung von z-l-asparaginsäure-dinatriumsalz aus fumarsäure

Publications (1)

Publication Number	Publication Date
SK5499A3 true SK5499A3 (en)	1999-08-06

Family

ID=3483243

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK54-99A SK5499A3 (en)	1998-02-02	1999-01-15	Process for the preparation of the disodium salt of z-l-aspartic acid from fumaric acid

Country Status (5)

Country	Link
EP (1)	EP0945517A3 (cs)
AT (1)	ATA16398A (cs)
CZ (1)	CZ10599A3 (cs)
HU (1)	HUP9900215A2 (cs)
SK (1)	SK5499A3 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT408755B (de) *	1998-05-22	2002-03-25	Dsm Fine Chem Austria Gmbh	Verfahren zur herstellung von l-asparaginsäure
CN106117070B (zh) *	2016-06-17	2018-09-28	宜兴市前成生物有限公司	一种制备l-天门冬氨酸二钠的方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3214345A (en) *	1958-11-20	1965-10-26	Tanabe Seiyaku Co	Process for producing l-aspartic acid
JPS5617073B2 (cs) *	1971-10-28	1981-04-20
JPS5626196A (en) *	1979-08-10	1981-03-13	Mitsubishi Petrochem Co Ltd	Preparation of l-aspartic acid
EP0612784B1 (de) *	1993-02-22	1998-11-11	Bayer Ag	Verfahren zur Herstellung von Polysuccinimid und Polyasparaginsäure
DE4306412A1 (de) *	1993-03-02	1994-09-08	Bayer Ag	Verfahren zur Herstellung von Polyasparaginsäure
JP2798886B2 (ja) *	1994-05-17	1998-09-17	株式会社日本触媒	Ｌ−アスパラギン酸の製造方法
EP0832982B1 (de) *	1996-09-20	2002-05-15	DSM Fine Chemicals Austria Nfg GmbH & Co KG	Verfahren zur Herstellung von Z-L-Asparaginsäure-Dinatriumsalz aus Fumarsäure

1998
- 1998-02-02 AT AT0016398A patent/ATA16398A/de not_active Application Discontinuation
1999
- 1999-01-13 CZ CZ99105A patent/CZ10599A3/cs unknown
- 1999-01-15 SK SK54-99A patent/SK5499A3/sk unknown
- 1999-01-28 EP EP99101849A patent/EP0945517A3/de not_active Withdrawn
- 1999-02-01 HU HU9900215A patent/HUP9900215A2/hu unknown

Also Published As

Publication number	Publication date
HUP9900215A2 (hu)	1999-10-28
ATA16398A (de)	2001-06-15
HU9900215D0 (en)	1999-04-28
EP0945517A2 (de)	1999-09-29
CZ10599A3 (cs)	1999-08-11
EP0945517A3 (de)	2000-08-02

Publication	Publication Date	Title
EP0127411B1 (en)	1988-08-10	Method of preparing alpha-l-aspartyl-l-phenylalanine methyl ester and its hydrochloride
US6072083A (en)	2000-06-06	Method for purifying branched chain amino acids
EP0748791B1 (en)	1999-11-17	Valine p-isopropylbenzene sulfonate and a process for purifying valine
CA1209942A (en)	1986-08-19	Process for producing an addition compound of a dipeptide ester and an amino acid ester
JP3528205B2 (ja)	2004-05-17	Ｌ−３，４−ジヒドロキシフェニルアラニンの製造方法
US5952206A (en)	1999-09-14	Process for preparing L-aspartic acid
SK5499A3 (en)	1999-08-06	Process for the preparation of the disodium salt of z-l-aspartic acid from fumaric acid
US5530160A (en)	1996-06-25	Process for the preparation of L-aspartic acid from ammonium aspartate
US5902737A (en)	1999-05-11	Process for the preparation of disodium benzyloxycarbonyl-L-aspartate from fumaric acid
EP0154472B1 (en)	1989-10-11	Process for the production of l-aspartyl-l-phenylalanine ester
US6008403A (en)	1999-12-28	Method for producing optically active amino acid of derivative thereof having high optical purity
CA1303628C (en)	1992-06-16	Method for racemization of optically active serine
EP1380570A1 (en)	2004-01-14	Process for producing n-formylamino acid and utilization thereof
JPH01120298A (ja)	1989-05-12	光学的に純粋なホモフエニルアラニンの製法
US6258572B1 (en)	2001-07-10	Process for preparing L-aspartic acid
US5120855A (en)	1992-06-09	Formation of hydroxyaromatic ketoacetal from a hydroxyaromatic methylketone and production of 5-(4'-hydroxyphenyl)hydantoin and Dp-hydroxyphenylglycine from 4-hydroxyacetophenone
JPH0634751B2 (ja)	1994-05-11	Ｄ−フエニルアラニンの分離方法
CA1322626C (en)	1993-09-28	Process for the preparation of aspartylphenylalanine methyl ester from n-formylaspartylphenylalanine methyl ester
JP2001316342A (ja)	2001-11-13	イソロイシンの精製法
JPH0623149B2 (ja)	1994-03-30	高純度ｎ−アセチル−ｄｌ−アミノ酸の製造方法
JPH0362398B2 (cs)	1991-09-25