GB1336650A - Process for the preparation of aspartyl aminoacid esters involving little racemization - Google Patents
Process for the preparation of aspartyl aminoacid esters involving little racemizationInfo
- Publication number
- GB1336650A GB1336650A GB1582971*[A GB1582971A GB1336650A GB 1336650 A GB1336650 A GB 1336650A GB 1582971 A GB1582971 A GB 1582971A GB 1336650 A GB1336650 A GB 1336650A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino acid
- ester
- aspartyl
- carbobenzoxy
- esters
- 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
- 235000001014 amino acid Nutrition 0.000 title abstract 10
- -1 aspartyl aminoacid esters Chemical class 0.000 title abstract 7
- 230000006340 racemization Effects 0.000 title 1
- 150000002148 esters Chemical class 0.000 abstract 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- XYXYXSKSTZAEJW-UHFFFAOYSA-N 2-(phenylmethoxycarbonylamino)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)NC(=O)OCC1=CC=CC=C1 XYXYXSKSTZAEJW-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- YEJSPQZHMWGIGP-YFKPBYRVSA-N L-glutamic acid, dimethyl ester Chemical compound COC(=O)CC[C@H](N)C(=O)OC YEJSPQZHMWGIGP-YFKPBYRVSA-N 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- BYHXBBOSJKPUJL-BYPYZUCNSA-N dimethyl (2s)-2-aminobutanedioate Chemical compound COC(=O)C[C@H](N)C(=O)OC BYHXBBOSJKPUJL-BYPYZUCNSA-N 0.000 abstract 1
- YEJSPQZHMWGIGP-UHFFFAOYSA-N dl-glutamic acid dimethyl ester Natural products COC(=O)CCC(N)C(=O)OC YEJSPQZHMWGIGP-UHFFFAOYSA-N 0.000 abstract 1
- 235000003599 food sweetener Nutrition 0.000 abstract 1
- 229910052806 inorganic carbonate Inorganic materials 0.000 abstract 1
- SZJUWKPNWWCOPG-UHFFFAOYSA-N methyl 2-anilinoacetate Chemical compound COC(=O)CNC1=CC=CC=C1 SZJUWKPNWWCOPG-UHFFFAOYSA-N 0.000 abstract 1
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 239000003765 sweetening agent Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 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
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
- A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/801—Peptide sweetners
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7007176A NL7007176A (en) | 1970-05-19 | 1970-05-19 | Sweet aspartylaminoacid esters prepn |
| NL7016630A NL7016630A (en) | 1970-11-13 | 1970-11-13 | Sweet aspartylaminoacid esters prepn |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1336650A true GB1336650A (en) | 1973-11-07 |
Family
ID=26644544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1582971*[A Expired GB1336650A (en) | 1970-05-19 | 1971-05-19 | Process for the preparation of aspartyl aminoacid esters involving little racemization |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3808190A (enExample) |
| JP (1) | JPS5336446B1 (enExample) |
| BE (1) | BE767299A (enExample) |
| CH (1) | CH553751A (enExample) |
| DE (1) | DE2125065A1 (enExample) |
| FR (1) | FR2091628A5 (enExample) |
| GB (1) | GB1336650A (enExample) |
| IT (1) | IT989588B (enExample) |
| SE (1) | SE393602B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4345091A (en) | 1980-02-04 | 1982-08-17 | Ajinomoto Company Incorporated | Method of producing N-benzyloxycarbonyl-L-aspartic acid |
| FR2551059A1 (fr) * | 1983-08-26 | 1985-03-01 | Hatco Chemical Corp | Procede de synthese d'acide n-benzyloxycarbonyl-l-aspartique et acide n-benzyloxycarbonyl-l-aspartique obtenu par ledit procede |
| GB2153365A (en) * | 1984-01-26 | 1985-08-21 | Pierrel Spa | Process for the preparation of N-acyl-derivatives of aspartame |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH589609A5 (enExample) * | 1972-03-29 | 1977-07-15 | Takeda Chemical Industries Ltd | |
| AU472355B2 (en) * | 1972-07-17 | 1976-05-20 | Takeda Chemical Industries, Ltd | Dipeptide esters and production thereof |
| US3901871A (en) * | 1973-09-21 | 1975-08-26 | American Cyanamid Co | Process of preparing ' -l-aspartyl-l-phenylalanine methyl ester |
| DE2857828C2 (enExample) * | 1977-01-27 | 1990-06-07 | Toyo Soda Mfg. Co., Ltd., Shinnanyo, Yamaguchi, Jp | |
| US4111925A (en) * | 1977-10-14 | 1978-09-05 | Monsanto Company | Hydrolysis of esters of α-L-aspartyl-L-phenylalanine |
| JPS5535059A (en) * | 1978-09-05 | 1980-03-11 | Ajinomoto Co Inc | Preparation of lower alkyl ester of alpha-l-aspartyl-l- phenylalanine |
| DE3066228D1 (en) * | 1980-03-03 | 1984-04-05 | Ajinomoto Kk | Process for the production of an alpha-l-aspartyl-l-phenylalanine lower alkyl ester and an intermediate therefor |
| US4293706A (en) * | 1980-06-19 | 1981-10-06 | Ppg Industries, Inc. | Preparation of N-benzyloxycarbonyl aspartic acid |
| US4450284A (en) * | 1981-08-10 | 1984-05-22 | Ppg Industries, Inc. | Method for purifying N-benzyloxycarbonyl aspartic acid |
| US4465626A (en) * | 1981-09-08 | 1984-08-14 | Pfizer Inc. | Process for preparation, isolation and purification of dipeptide sweeteners |
| EP0075160B1 (en) * | 1981-09-21 | 1987-01-07 | Toyo Soda Manufacturing Co., Ltd. | Process for recovering a dipeptide derivative |
| US4440677A (en) * | 1983-06-20 | 1984-04-03 | G. D. Searle & Co. | Method and intermediates for producing α-L-aspartyl-L-phenylalanine |
| US4570015A (en) * | 1983-08-26 | 1986-02-11 | Hatco Chemical Corporation | Preparation of large crystals of N-benzyloxycarbonyl-L-aspartic acid |
| US4523026A (en) * | 1983-08-26 | 1985-06-11 | Hatco Chemical Corporation | Synthesis of N-benzyloxycarbonyl-L-aspartic acid |
| US4484001A (en) * | 1983-11-18 | 1984-11-20 | Ppg Industries, Inc. | Method for preparing N-benzyloxycarbonyl amino acids containing additional functionality |
| US4500726A (en) * | 1984-05-23 | 1985-02-19 | Ppg Industries, Inc. | Method for preparing N-benzyloxycarbonyl amino acids containing additional functionality |
| JPH0680074B2 (ja) * | 1985-07-01 | 1994-10-12 | 味の素株式会社 | Ｎ―ホルミル―Ｌ―α―アスパルチル―Ｌ―フェニルアラニンの製法 |
| EP0510552B2 (en) * | 1991-04-24 | 2000-11-15 | MITSUI TOATSU CHEMICALS, Inc. | Preparation process of alpha-aspartyl-L-phenylalanine methyl ester |
| DE19842952A1 (de) | 1998-09-18 | 2000-03-23 | Basf Ag | Dispergiermittel |
| CN101421293B (zh) * | 2006-03-01 | 2013-09-25 | 福冈县政府 | 含有肽脂质的载体和使用该载体将化合物引入细胞的方法 |
-
1971
- 1971-05-13 CH CH713671A patent/CH553751A/xx not_active IP Right Cessation
- 1971-05-14 FR FR7117531A patent/FR2091628A5/fr not_active Expired
- 1971-05-17 IT IT50379/71A patent/IT989588B/it active
- 1971-05-18 BE BE767299A patent/BE767299A/xx unknown
- 1971-05-18 US US00144639A patent/US3808190A/en not_active Expired - Lifetime
- 1971-05-19 SE SE7106515A patent/SE393602B/xx unknown
- 1971-05-19 DE DE19712125065 patent/DE2125065A1/de not_active Ceased
- 1971-05-19 JP JP3397271A patent/JPS5336446B1/ja active Pending
- 1971-05-19 GB GB1582971*[A patent/GB1336650A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4345091A (en) | 1980-02-04 | 1982-08-17 | Ajinomoto Company Incorporated | Method of producing N-benzyloxycarbonyl-L-aspartic acid |
| FR2551059A1 (fr) * | 1983-08-26 | 1985-03-01 | Hatco Chemical Corp | Procede de synthese d'acide n-benzyloxycarbonyl-l-aspartique et acide n-benzyloxycarbonyl-l-aspartique obtenu par ledit procede |
| GB2149396A (en) * | 1983-08-26 | 1985-06-12 | Hatco Chemical Corp | N-benzyloxycarbonyl-l-aspartic acid |
| GB2153365A (en) * | 1984-01-26 | 1985-08-21 | Pierrel Spa | Process for the preparation of N-acyl-derivatives of aspartame |
Also Published As
| Publication number | Publication date |
|---|---|
| SE393602B (sv) | 1977-05-16 |
| FR2091628A5 (enExample) | 1972-01-14 |
| IT989588B (it) | 1975-06-10 |
| JPS5336446B1 (enExample) | 1978-10-03 |
| BE767299A (fr) | 1971-11-18 |
| US3808190A (en) | 1974-04-30 |
| DE2125065A1 (de) | 1971-12-02 |
| CH553751A (de) | 1974-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |