AU2001264678A1 - Synthesis of n-(n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methylester by reductive alkylation and crystallization/isolation in aqueous methanol - Google Patents

Synthesis of n-(n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methylester by reductive alkylation and crystallization/isolation in aqueous methanol

Info

Publication number
AU2001264678A1
AU2001264678A1 AU2001264678A AU6467801A AU2001264678A1 AU 2001264678 A1 AU2001264678 A1 AU 2001264678A1 AU 2001264678 A AU2001264678 A AU 2001264678A AU 6467801 A AU6467801 A AU 6467801A AU 2001264678 A1 AU2001264678 A1 AU 2001264678A1
Authority
AU
Australia
Prior art keywords
aspartyl
dimethylbutyl
phenylalanine
alpha
crystallization
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.)
Abandoned
Application number
AU2001264678A
Inventor
Indra Prakash
Mike G Scaros
Kurt L. Wachholder
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nutrasweet Co
Original Assignee
Nutrasweet Co
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.)
Filing date
Publication date
Application filed by Nutrasweet Co filed Critical Nutrasweet Co
Publication of AU2001264678A1 publication Critical patent/AU2001264678A1/en
Abandoned legal-status Critical Current

Links

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

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Seasonings (AREA)

Abstract

N-[N-(3,3-dimethylbutyl)-L-alpha-aspartyl]-L-phenylalanine 1-methyl ester is produced by reductive alkylation and crystallization/isolation in methanol and water. The production method is efficient and low cost, as compared with conventional N-[N-(3,3-dimethylbutyl)-L-alpha-aspartyl]-L-phenylalanine 1-methyl ester synthesis and results in high purity N-[N-(3,3-dimethylbutyl)-L-alpha-aspartyl]-L-phenylalanine 1-methyl ester.
AU2001264678A 2000-05-18 2001-05-18 Synthesis of n-(n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methylester by reductive alkylation and crystallization/isolation in aqueous methanol Abandoned AU2001264678A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/572,843 US6281380B1 (en) 2000-05-18 2000-05-18 Synthesis of N-(N-(3,3-dimethylbutyl)-L-α-aspartyl)L-phenylalanine1-methyl ester by reductive alkylation and crystallization/ isolation in aqueous methanol
US09572843 2000-05-18
PCT/US2001/016143 WO2001087926A2 (en) 2000-05-18 2001-05-18 SYNTHESIS OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER BY REDUCTIVE ALKYLATION AND CRYSTALLIZATION/ISOLATION IN AQUEOUS METHANOL

Publications (1)

Publication Number Publication Date
AU2001264678A1 true AU2001264678A1 (en) 2001-11-26

Family

ID=24289587

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2001264678A Abandoned AU2001264678A1 (en) 2000-05-18 2001-05-18 Synthesis of n-(n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methylester by reductive alkylation and crystallization/isolation in aqueous methanol

Country Status (7)

Country Link
US (1) US6281380B1 (en)
EP (1) EP1284990B1 (en)
AT (1) ATE282046T1 (en)
AU (1) AU2001264678A1 (en)
DE (1) DE60107079T2 (en)
ES (1) ES2228876T3 (en)
WO (1) WO2001087926A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006528648A (en) * 2003-07-24 2006-12-21 ザ クイーンズ メディカル センター Preparation and use of alkylating agents

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL9201408A (en) * 1992-08-05 1994-03-01 Holland Sweetener Co Method for crystallizing aspartame.
FR2697844B1 (en) * 1992-11-12 1995-01-27 Claude Nofre New compounds derived from dipeptides or dipeptide analogues useful as sweetening agents, process for their preparation.
US5728862A (en) * 1997-01-29 1998-03-17 The Nutrasweet Company Method for preparing and purifying an N-alkylated aspartame derivative
JPH11130794A (en) * 1997-10-23 1999-05-18 Ajinomoto Co Inc Purification of aspartame derivative
NL1010063C2 (en) * 1998-09-10 2000-03-13 Holland Sweetener Co Method for the preparation of neotame.
US6077962A (en) * 1998-12-24 2000-06-20 The Nutrasweet Company 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

Also Published As

Publication number Publication date
EP1284990B1 (en) 2004-11-10
ES2228876T3 (en) 2005-04-16
EP1284990A2 (en) 2003-02-26
ATE282046T1 (en) 2004-11-15
DE60107079T2 (en) 2005-11-10
WO2001087926A3 (en) 2002-03-21
US6281380B1 (en) 2001-08-28
DE60107079D1 (en) 2004-12-16
WO2001087926A2 (en) 2001-11-22

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