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AU2001263267A1 - Synthesis of n-(n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methylester using l-alpha-aspartyl-l-phenylalanine 1-methyl ester precursors - Google Patents

Synthesis of n-(n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methylester using l-alpha-aspartyl-l-phenylalanine 1-methyl ester precursors

Info

Publication number
AU2001263267A1
AU2001263267A1 AU2001263267A AU6326701A AU2001263267A1 AU 2001263267 A1 AU2001263267 A1 AU 2001263267A1 AU 2001263267 A AU2001263267 A AU 2001263267A AU 6326701 A AU6326701 A AU 6326701A AU 2001263267 A1 AU2001263267 A1 AU 2001263267A1
Authority
AU
Australia
Prior art keywords
aspartyl
phenylalanine
alpha
methyl ester
dimethylbutyl
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
AU2001263267A
Inventor
Zhi Guo
Indra Prakash
Steve Schroeder
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 AU2001263267A1 publication Critical patent/AU2001263267A1/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 hydrogenation of a mixture of 3,3-dimethylbutyraldehyde and a precursor of L-alpha-aspartyl-L-phenylalanine 1-methyl ester. In particular, N-[N-(3,3-dimethylbutyl)-L-alpha-aspartyl]-L-phenylalanine 1-methyl ester is produced using an acid salt of L-alpha-aspartyl-L-phenylalanine 1-methyl ester or N-protected L-alpha-aspartyl-L-phenylalanine 1-methyl ester. 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.
AU2001263267A 2000-05-18 2001-05-18 Synthesis of n-(n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methylester using l-alpha-aspartyl-l-phenylalanine 1-methyl ester precursors Abandoned AU2001263267A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US20510500P 2000-05-18 2000-05-18
US60205105 2000-05-18
PCT/US2001/016146 WO2001087927A2 (en) 2000-05-18 2001-05-18 gYNTHESIS OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER USING L-α-ASPARTYL-L-PHENYLALANINE 1-METHYL ESTER PRECURSORS

Publications (1)

Publication Number Publication Date
AU2001263267A1 true AU2001263267A1 (en) 2001-11-26

Family

ID=22760810

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2001263267A Abandoned AU2001263267A1 (en) 2000-05-18 2001-05-18 Synthesis of n-(n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methylester using l-alpha-aspartyl-l-phenylalanine 1-methyl ester precursors

Country Status (7)

Country Link
US (1) US6642406B2 (en)
EP (1) EP1280818B1 (en)
AT (2) ATE310013T1 (en)
AU (1) AU2001263267A1 (en)
DE (2) DE60115106T2 (en)
ES (2) ES2253626T3 (en)
WO (1) WO2001087927A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040258821A1 (en) * 2003-04-17 2004-12-23 Depauw Justin L. Filtration of dipeptide and dipeptide derivative sweeteners
CN101565450A (en) * 2003-05-06 2009-10-28 纽特拉斯威特公司 N-[N-(3,3-dimethylbutyl)-L-alpha-aspartyl]-L-phenylalanine 1-methyl ester
US7523774B2 (en) * 2005-01-19 2009-04-28 The Goodyear Tire & Rubber Company Pneumatic tire with high turnup, locked bead construction
CN109467586B (en) * 2018-12-15 2021-06-22 济南诚汇双达化工有限公司 Neotame refining method
CN110467648B (en) * 2019-07-24 2021-12-21 江苏理工学院 Preparation method for removing neotame peculiar smell

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4946988A (en) * 1988-07-14 1990-08-07 The Nutrasweet Company Process for the preparation of α-L-aspartyl-L-phenylalanine methyl ester hydrochloride by use of isolated N-formyl L-aspartic anhydride
JP2970107B2 (en) 1991-05-23 1999-11-02 味の素株式会社 Method for producing α-L-aspartyl-L-phenylalanine methyl ester
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.
FR2719590B1 (en) * 1994-05-09 1996-07-26 Claude Nofre Improved process for the preparation of a compound derived from aspartame useful as a sweetening agent.
US5728862A (en) 1997-01-29 1998-03-17 The Nutrasweet Company Method for preparing and purifying an N-alkylated aspartame derivative
NL1010063C2 (en) 1998-09-10 2000-03-13 Holland Sweetener Co Method for the preparation of neotame.

Also Published As

Publication number Publication date
US6642406B2 (en) 2003-11-04
DE60108739D1 (en) 2005-03-10
DE60115106D1 (en) 2005-12-22
ATE288445T1 (en) 2005-02-15
DE60108739T2 (en) 2005-06-23
WO2001087927A3 (en) 2002-05-10
ATE310013T1 (en) 2005-12-15
ES2253626T3 (en) 2006-06-01
EP1280818B1 (en) 2005-02-02
US20020019557A1 (en) 2002-02-14
DE60115106T2 (en) 2006-07-13
EP1280818A2 (en) 2003-02-05
WO2001087927A2 (en) 2001-11-22
ES2233644T3 (en) 2005-06-16

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