ATE550346T1 - Synthese von n-än-(3,3-dimethylbutyl)-l-alpha- aspartylü - l-phenylalanin-1-methylester unter verwendung von 3,3- dimethylbutyraldehyddimethylacetal als vorläufer - Google Patents
Synthese von n-än-(3,3-dimethylbutyl)-l-alpha- aspartylü - l-phenylalanin-1-methylester unter verwendung von 3,3- dimethylbutyraldehyddimethylacetal als vorläuferInfo
- Publication number
- ATE550346T1 ATE550346T1 AT04751149T AT04751149T ATE550346T1 AT E550346 T1 ATE550346 T1 AT E550346T1 AT 04751149 T AT04751149 T AT 04751149T AT 04751149 T AT04751149 T AT 04751149T AT E550346 T1 ATE550346 T1 AT E550346T1
- Authority
- AT
- Austria
- Prior art keywords
- dimethylbutyl
- phenylalanine
- methyl ester
- dimethylbutyraldehyde
- synthesis
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 239000002243 precursor Substances 0.000 title 1
- LTNUSYNQZJZUSY-UHFFFAOYSA-N 3,3-dimethylbutanal Chemical compound CC(C)(C)CC=O LTNUSYNQZJZUSY-UHFFFAOYSA-N 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 235000010357 aspartame Nutrition 0.000 abstract 1
- 150000007857 hydrazones Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- HLIAVLHNDJUHFG-UHFFFAOYSA-N neotame Chemical compound CC(C)(C)CCNC(CC(O)=O)C(=O)NC(C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-UHFFFAOYSA-N 0.000 abstract 1
- 238000007248 oxidative elimination reaction Methods 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 229960005190 phenylalanine Drugs 0.000 abstract 1
- 230000001172 regenerating effect Effects 0.000 abstract 1
- 150000007659 semicarbazones Chemical class 0.000 abstract 1
- 239000013638 trimer Substances 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
-
- 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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Seasonings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46807603P | 2003-05-06 | 2003-05-06 | |
| PCT/US2004/013625 WO2004101604A2 (en) | 2003-05-06 | 2004-04-30 | SYNTHESIS OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER USING 3,3-DIMETHYLBUTYRALDEHYDE PRECURSORS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE550346T1 true ATE550346T1 (de) | 2012-04-15 |
Family
ID=33452184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT04751149T ATE550346T1 (de) | 2003-05-06 | 2004-04-30 | Synthese von n-än-(3,3-dimethylbutyl)-l-alpha- aspartylü - l-phenylalanin-1-methylester unter verwendung von 3,3- dimethylbutyraldehyddimethylacetal als vorläufer |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US7288670B2 (de) |
| EP (2) | EP2138506A3 (de) |
| JP (2) | JP4602982B2 (de) |
| KR (3) | KR101108256B1 (de) |
| CN (4) | CN101565451B (de) |
| AT (1) | ATE550346T1 (de) |
| WO (1) | WO2004101604A2 (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101775066B (zh) * | 2010-01-29 | 2012-05-02 | 常茂生物化学工程股份有限公司 | 一种合成纽甜的方法 |
| CN102295541B (zh) * | 2011-08-16 | 2013-04-17 | 济南诚汇双达化工有限公司 | 一种3,3-二甲基丁醛的制备方法 |
| CN104045688B (zh) * | 2014-06-18 | 2016-09-14 | 山东诚汇双达药业有限公司 | 一种纽甜的合成方法 |
| CN105504006B (zh) * | 2016-01-28 | 2019-01-04 | 柳玉荣 | 一种提高纽甜质量的合成方法 |
| CN105541965B (zh) * | 2016-01-28 | 2019-01-18 | 柳玉荣 | 一种提高纽甜得率的合成方法 |
| 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 (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1038102A (en) | 1911-12-09 | 1912-09-10 | Farbenfab Vorm Bayer F & Co | 2-alkoxy-5-monosubstituted barbituric acids. |
| 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 |
| RU2179979C1 (ru) * | 1998-04-09 | 2002-02-27 | Адзиномото Ко., Инк. | Сложноэфирные производные аспартилдипептидов и подслащивающие вещества |
| US5905175A (en) * | 1998-05-20 | 1999-05-18 | The Nutrasweet Company | Synthesis and purification of 3,3-dimethylbutyraldehyde via oxidation of 1-chloro-3,3-dimethylbutane with dimethyl sulfoxide |
| NL1010063C2 (nl) | 1998-09-10 | 2000-03-13 | Holland Sweetener Co | Werkwijze voor de bereiding van neotaam. |
| AU1832500A (en) * | 1998-11-25 | 2000-06-19 | Nutrasweet Company, The | Purification of N-(N-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methyl ester via crystallization |
| US6573409B1 (en) * | 1999-07-02 | 2003-06-03 | The Nutrasweet Company | Process for the preparation of 3,3-dimethylbutanal |
| ES2233644T3 (es) * | 2000-05-18 | 2005-06-16 | The Nutrasweet Company | Sintesis de n-(n-3,3 -dimetilbutil) -l-alfa aspartil)-l- fenilalanina 1- metil ester por utilizacion de precursores de l-alfa-aspartatil-l.-fenilalanina 1-metil ester. |
| US6720446B2 (en) * | 2001-11-05 | 2004-04-13 | The Nutrasweet Company | Catalyst modification to enhance neotame production |
-
2004
- 2004-04-30 KR KR1020057020999A patent/KR101108256B1/ko not_active Expired - Fee Related
- 2004-04-30 CN CN2009101265259A patent/CN101565451B/zh not_active Expired - Fee Related
- 2004-04-30 JP JP2006532539A patent/JP4602982B2/ja not_active Expired - Fee Related
- 2004-04-30 EP EP09171874A patent/EP2138506A3/de not_active Withdrawn
- 2004-04-30 AT AT04751149T patent/ATE550346T1/de active
- 2004-04-30 CN CN200910126523XA patent/CN101565449B/zh not_active Expired - Fee Related
- 2004-04-30 EP EP04751149A patent/EP1620458B1/de not_active Expired - Lifetime
- 2004-04-30 KR KR1020117010054A patent/KR20110060969A/ko not_active Ceased
- 2004-04-30 CN CNB2004800120455A patent/CN100482681C/zh not_active Expired - Fee Related
- 2004-04-30 CN CNA2009101265244A patent/CN101565450A/zh active Pending
- 2004-04-30 US US10/834,933 patent/US7288670B2/en not_active Expired - Fee Related
- 2004-04-30 KR KR1020117026260A patent/KR101127519B1/ko not_active Expired - Fee Related
- 2004-04-30 WO PCT/US2004/013625 patent/WO2004101604A2/en not_active Ceased
-
2007
- 2007-09-19 US US11/857,781 patent/US20080045744A1/en not_active Abandoned
-
2010
- 2010-05-12 US US12/778,306 patent/US8034969B2/en not_active Expired - Fee Related
- 2010-08-13 JP JP2010181289A patent/JP2011026323A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1784418A (zh) | 2006-06-07 |
| US20100222608A1 (en) | 2010-09-02 |
| JP2007529419A (ja) | 2007-10-25 |
| CN101565449A (zh) | 2009-10-28 |
| CN101565451B (zh) | 2013-03-27 |
| US20040236140A1 (en) | 2004-11-25 |
| JP4602982B2 (ja) | 2010-12-22 |
| KR20110126191A (ko) | 2011-11-22 |
| CN101565450A (zh) | 2009-10-28 |
| US7288670B2 (en) | 2007-10-30 |
| EP2138506A3 (de) | 2010-04-21 |
| KR101108256B1 (ko) | 2012-01-31 |
| CN101565451A (zh) | 2009-10-28 |
| CN100482681C (zh) | 2009-04-29 |
| JP2011026323A (ja) | 2011-02-10 |
| US8034969B2 (en) | 2011-10-11 |
| EP1620458A2 (de) | 2006-02-01 |
| EP1620458B1 (de) | 2012-03-21 |
| EP2138506A2 (de) | 2009-12-30 |
| CN101565449B (zh) | 2012-05-30 |
| KR20060013385A (ko) | 2006-02-09 |
| US20080045744A1 (en) | 2008-02-21 |
| KR101127519B1 (ko) | 2012-03-22 |
| WO2004101604A2 (en) | 2004-11-25 |
| KR20110060969A (ko) | 2011-06-08 |
| WO2004101604A3 (en) | 2005-03-31 |
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