ATE202146T1 - Verbesserte enzymatische kupplungsreaktion von n- geschützte l-asparaginsäure und phenylalaninmethylester - Google Patents
Verbesserte enzymatische kupplungsreaktion von n- geschützte l-asparaginsäure und phenylalaninmethylesterInfo
- Publication number
- ATE202146T1 ATE202146T1 AT96202653T AT96202653T ATE202146T1 AT E202146 T1 ATE202146 T1 AT E202146T1 AT 96202653 T AT96202653 T AT 96202653T AT 96202653 T AT96202653 T AT 96202653T AT E202146 T1 ATE202146 T1 AT E202146T1
- Authority
- AT
- Austria
- Prior art keywords
- protected
- methyl ester
- phenylalanine methyl
- coupling reaction
- enzymatic coupling
- Prior art date
Links
- 238000005859 coupling reaction Methods 0.000 title abstract 4
- 230000002255 enzymatic effect Effects 0.000 title abstract 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 title 1
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 title 1
- 238000000034 method Methods 0.000 abstract 3
- 239000002244 precipitate Substances 0.000 abstract 3
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229960005261 aspartic acid Drugs 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000010924 continuous production Methods 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 230000009849 deactivation Effects 0.000 abstract 1
- VSDUZFOSJDMAFZ-UHFFFAOYSA-N methyl 2-amino-3-phenylpropanoate Chemical compound COC(=O)C(N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-UHFFFAOYSA-N 0.000 abstract 1
- 108010009355 microbial metalloproteinases Proteins 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
-
- 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
- C12P21/00—Preparation of peptides or proteins
-
- 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
- C12P21/00—Preparation of peptides or proteins
- C12P21/02—Preparation of peptides or proteins having a known sequence of two or more amino acids, e.g. glutathione
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biophysics (AREA)
- Medicinal Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95202744 | 1995-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE202146T1 true ATE202146T1 (de) | 2001-06-15 |
Family
ID=8220708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT96202653T ATE202146T1 (de) | 1995-10-11 | 1996-09-23 | Verbesserte enzymatische kupplungsreaktion von n- geschützte l-asparaginsäure und phenylalaninmethylester |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5693485A (de) |
| JP (1) | JPH09271389A (de) |
| KR (1) | KR970021094A (de) |
| AT (1) | ATE202146T1 (de) |
| DE (1) | DE69613305T2 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6225493B1 (en) * | 2000-08-21 | 2001-05-01 | The Nutrasweet Company | Metal ion assisted N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester isomer resolution |
| EP1264896A1 (de) * | 2001-06-07 | 2002-12-11 | Holland Sweetener Company V.o.F. | Enzymatische Kupplung von L-Phenylalaninemethylester und N-Benzyloxycarbonyl-Asparagensäure in einem kontinuierlichen oder fed-batch Verfahren |
| US20110098477A1 (en) * | 2005-06-28 | 2011-04-28 | Chugai Seiyaku Kabushiki Kaisha | Method Of Producing Compound Having Anti-Hcv Activity |
| US9101160B2 (en) | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
| US8017168B2 (en) | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2801238C2 (de) * | 1977-01-27 | 1986-06-05 | (Zaidanhojin) Sagami Chemical Research Center, Tokio/Tokyo | Verfahren zur Herstellung von Salzen aus L,L-Dipeptiden und Phenylalaninestern |
| JPS55135595A (en) * | 1979-04-03 | 1980-10-22 | Toyo Soda Mfg Co Ltd | Preparation of dipeptide |
| EP0075160B1 (de) * | 1981-09-21 | 1987-01-07 | Toyo Soda Manufacturing Co., Ltd. | Verfahren zur Gewinnung eines Dipeptidderivates |
| JPS5917997A (ja) * | 1982-07-23 | 1984-01-30 | Toyo Soda Mfg Co Ltd | ジペプチドエステルとアミノ酸エステルとの付加化合物の製造方法 |
| US4873359A (en) * | 1985-10-21 | 1989-10-10 | W. R. Grace & Co. - Conn. | Process for preparing as partyl-phenylalanine dipeptides |
| US5002872A (en) * | 1989-05-10 | 1991-03-26 | W. R. Grace & Co.-Conn. | Enzyme mediated coupling reactions |
| KR930002966B1 (ko) * | 1990-11-24 | 1993-04-16 | 주식회사 미 원 | 디펩티드의 제조방법 |
| US5279946A (en) * | 1991-07-10 | 1994-01-18 | Development Center For Biotechnology | Process for the preparation of N-benzyloxycarbonyl-alpha-L-aspartyl-L-phenylalanine methyl ester |
-
1996
- 1996-09-23 DE DE69613305T patent/DE69613305T2/de not_active Expired - Fee Related
- 1996-09-23 AT AT96202653T patent/ATE202146T1/de not_active IP Right Cessation
- 1996-10-10 KR KR1019960046010A patent/KR970021094A/ko not_active Ceased
- 1996-10-11 JP JP8269795A patent/JPH09271389A/ja active Pending
- 1996-10-11 US US08/729,507 patent/US5693485A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69613305T2 (de) | 2002-05-02 |
| DE69613305D1 (de) | 2001-07-19 |
| US5693485A (en) | 1997-12-02 |
| KR970021094A (ko) | 1997-05-28 |
| JPH09271389A (ja) | 1997-10-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties |