DE69911061D1 - N-3, 3-dimethylbutyl-l-asparaginsäure und ihre ester, verfahren zur herstellung dieser und das verfahren um daraus n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanin-1-methylester herzustellen - Google Patents
N-3, 3-dimethylbutyl-l-asparaginsäure und ihre ester, verfahren zur herstellung dieser und das verfahren um daraus n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanin-1-methylester herzustellenInfo
- Publication number
- DE69911061D1 DE69911061D1 DE69911061T DE69911061T DE69911061D1 DE 69911061 D1 DE69911061 D1 DE 69911061D1 DE 69911061 T DE69911061 T DE 69911061T DE 69911061 T DE69911061 T DE 69911061T DE 69911061 D1 DE69911061 D1 DE 69911061D1
- Authority
- DE
- Germany
- Prior art keywords
- dimethylbutyl
- phenylalanine
- aspartyl
- alpha
- methylester
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract 2
- -1 3,3-DIMETHYLBUTYL Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000004702 methyl esters Chemical class 0.000 title 1
- SOEVTYGIGRHGQE-ZETCQYMHSA-N (2s)-2-(3,3-dimethylbutylamino)butanedioic acid Chemical compound CC(C)(C)CCN[C@H](C(O)=O)CC(O)=O SOEVTYGIGRHGQE-ZETCQYMHSA-N 0.000 abstract 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract 4
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 abstract 2
- 229960005190 phenylalanine Drugs 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- HLIAVLHNDJUHFG-HOTGVXAUSA-N neotame Chemical compound CC(C)(C)CCN[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-HOTGVXAUSA-N 0.000 abstract 1
- 238000005897 peptide coupling reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/219,898 US6077962A (en) | 1998-12-24 | 1998-12-24 | N-3, 3-dimethylbutyl-L-aspartic acid and esters thereof, the process of preparing the same, and the process for preparing N-(N-(3,3-dimethylbutyl) -α L-aspartyl)-L- phenylalanine 1-methyl ester therefrom |
| US219898 | 1998-12-24 | ||
| PCT/US1999/029064 WO2000039075A1 (en) | 1998-12-24 | 1999-12-08 | N-3, 3-DIMETHYLBUTYL-L-ASPARTIC ACID AND ESTERS THEREOF, THE PROCESS OF PREPARING THE SAME, AND THE PROCESS FOR PREPARING N-[N-(3, 3-DIMENTHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER THEREFROM |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69911061D1 true DE69911061D1 (de) | 2003-10-09 |
| DE69911061T2 DE69911061T2 (de) | 2004-06-03 |
Family
ID=22821194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69911061T Expired - Lifetime DE69911061T2 (de) | 1998-12-24 | 1999-12-08 | N-3, 3-dimethylbutyl-l-asparaginsäure und ihre ester, verfahren zur herstellung dieser und das verfahren um daraus n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanin-1-methylester herzustellen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6077962A (de) |
| EP (1) | EP1140795B1 (de) |
| AT (1) | ATE248806T1 (de) |
| AU (1) | AU1751700A (de) |
| DE (1) | DE69911061T2 (de) |
| ES (1) | ES2201812T3 (de) |
| WO (1) | WO2000039075A1 (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001018034A1 (fr) * | 1999-09-07 | 2001-03-15 | Ajinomoto Co., Inc. | Procede de production de derive d'aspartame, procede de purification de ce derive, cristaux et utilisation de ce derive |
| US6627431B1 (en) * | 2000-05-12 | 2003-09-30 | The Nutrasweet Company | Chemoenzymatic synthesis of neotame |
| US6281380B1 (en) * | 2000-05-18 | 2001-08-28 | The Nutra Sweet Company | Synthesis of N-(N-(3,3-dimethylbutyl)-L-α-aspartyl)L-phenylalanine1-methyl ester by reductive alkylation and crystallization/ isolation in aqueous methanol |
| DE60108745T2 (de) | 2000-05-19 | 2005-07-07 | The Nutrasweet Co., Chicago | Herstellung von N-[N-(3,3-Dimethylbutyl)-L-α-aspartyl]-L-phenylalanin-1-methylester mittels Oxazolidinonderivate |
| 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 |
| KR20030020646A (ko) * | 2001-09-04 | 2003-03-10 | 한미약품공업 주식회사 | 2-(에스)-아미노-4-페닐부틸산의 개선된 제조방법 |
| SE0302986D0 (sv) * | 2003-11-13 | 2003-11-13 | Akzo Nobel Nv | Use of a derivative of aspartic acid as a collector in froth flotation processes |
| US10017388B2 (en) * | 2014-06-06 | 2018-07-10 | Massachusetts Institute Of Technology | Dihydrogen tetrametaphosphate, its derivatives, and preparation thereof |
| CN105152951A (zh) * | 2015-07-17 | 2015-12-16 | 宁波海硕药业科技有限公司 | 一种l-鸟氨酸·l-天门冬氨酸的制备方法 |
| CN110467648B (zh) * | 2019-07-24 | 2021-12-21 | 江苏理工学院 | 一种去除纽甜异味的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2697844B1 (fr) * | 1992-11-12 | 1995-01-27 | Claude Nofre | Nouveaux composés dérivés de dipeptides ou d'analogues dipeptidiques utiles comme agents édulcorants, leur procédé de préparation. |
| FR2719590B1 (fr) * | 1994-05-09 | 1996-07-26 | Claude Nofre | Procédé perfectionné de préparation d'un composé dérivé de l'aspartame utile comme agent édulcorant. |
| US5728862A (en) * | 1997-01-29 | 1998-03-17 | The Nutrasweet Company | Method for preparing and purifying an N-alkylated aspartame derivative |
-
1998
- 1998-12-24 US US09/219,898 patent/US6077962A/en not_active Expired - Fee Related
-
1999
- 1999-12-08 DE DE69911061T patent/DE69911061T2/de not_active Expired - Lifetime
- 1999-12-08 AT AT99960662T patent/ATE248806T1/de not_active IP Right Cessation
- 1999-12-08 ES ES99960662T patent/ES2201812T3/es not_active Expired - Lifetime
- 1999-12-08 WO PCT/US1999/029064 patent/WO2000039075A1/en active IP Right Grant
- 1999-12-08 AU AU17517/00A patent/AU1751700A/en not_active Abandoned
- 1999-12-08 EP EP99960662A patent/EP1140795B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6077962A (en) | 2000-06-20 |
| ES2201812T3 (es) | 2004-03-16 |
| AU1751700A (en) | 2000-07-31 |
| WO2000039075A1 (en) | 2000-07-06 |
| EP1140795B1 (de) | 2003-09-03 |
| DE69911061T2 (de) | 2004-06-03 |
| ATE248806T1 (de) | 2003-09-15 |
| EP1140795A1 (de) | 2001-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: NUTRASWEET PROPERTY HOLDINGS,INC., CHICAGO, II, US |