FR2453137A1 - Procede de preparation de dipeptides - Google Patents

Procede de preparation de dipeptides

Info

Publication number
FR2453137A1
FR2453137A1 FR8007552A FR8007552A FR2453137A1 FR 2453137 A1 FR2453137 A1 FR 2453137A1 FR 8007552 A FR8007552 A FR 8007552A FR 8007552 A FR8007552 A FR 8007552A FR 2453137 A1 FR2453137 A1 FR 2453137A1
Authority
FR
France
Prior art keywords
ester
dipeptides
phenylalanine
preparation process
water
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.)
Granted
Application number
FR8007552A
Other languages
English (en)
Other versions
FR2453137B1 (fr
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.)
Sagami Chemical Research Institute
Original Assignee
Sagami Chemical Research Institute
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 Sagami Chemical Research Institute filed Critical Sagami Chemical Research Institute
Publication of FR2453137A1 publication Critical patent/FR2453137A1/fr
Application granted granted Critical
Publication of FR2453137B1 publication Critical patent/FR2453137B1/fr
Expired 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
    • C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
    • C07K5/0613—Aspartame

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)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Procédé de fabrication de dipeptides à partir d'un dérivé de substitution sur l'azote de l'acide aspartique et d'un ester alkylique inférieur de la phénylalanine. On fait réagir ces deux substances dans un solvant organique non miscible à l'eau en présence d'une métallo-protéinase (protéinase métallifère) << immobilisée >>, c'est-à-dire fixée ou liée, contenant de l'eau. L'enzyme peut être ainsi récupérée après la réaction pour être réemployée, les pertes de matières par hydrolyse de l'ester de phénylalinine sont réduites, ce qui permet d'utiliser cet ester en quantité moindre tout en assurant des rendements accrus, et le coût d'une production industrielle s'en trouve abaissé. Application à la fabrication de l'ester méthylique de la L-aspartyl-L-phénylalanine, dont le pouvoir édulcorant est 200 fois supérieur à celui du saccharose.
FR8007552A 1979-04-03 1980-04-03 Procede de preparation de dipeptides Expired FR2453137B1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP4017079A JPS55135595A (en) 1979-04-03 1979-04-03 Preparation of dipeptide

Publications (2)

Publication Number Publication Date
FR2453137A1 true FR2453137A1 (fr) 1980-10-31
FR2453137B1 FR2453137B1 (fr) 1985-06-07

Family

ID=12573284

Family Applications (1)

Application Number Title Priority Date Filing Date
FR8007552A Expired FR2453137B1 (fr) 1979-04-03 1980-04-03 Procede de preparation de dipeptides

Country Status (10)

Country Link
US (1) US4284721A (fr)
JP (1) JPS55135595A (fr)
BE (1) BE882603A (fr)
CA (1) CA1133841A (fr)
CH (1) CH645341A5 (fr)
DE (1) DE3012693A1 (fr)
FR (1) FR2453137B1 (fr)
GB (1) GB2049703B (fr)
IT (1) IT1147338B (fr)
NL (1) NL8001902A (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2499098A1 (fr) * 1981-02-02 1982-08-06 Searle & Co Procede pour la production d'un ester d'alkyle de (l-aspartyl amino-protege)-l-phenylalanine
EP0074095A1 (fr) * 1981-09-05 1983-03-16 Toyo Soda Manufacturing Co., Ltd. Procédé de préparation d'esters alcoyliques de l'aspartylphénylalanine
EP0086053A1 (fr) * 1982-01-26 1983-08-17 Imahori Kazutomo Procédé de synthèse de peptides ou de dérivés peptidiques
FR2589480A1 (fr) * 1985-11-05 1987-05-07 Hoechst France Procede biologique de preparation de n-(n-benzyloxycarbonyl l-aspartyl-1) l-phenylalaninate de methyle
EP0269390A2 (fr) * 1986-11-21 1988-06-01 Genencor International, Inc. Production enzymatique de l'ester alcoylique de L-aspartyl-L-phénylalanine
EP0574028A1 (fr) * 1985-10-21 1993-12-15 Hampshire Chemical Corp. Analoques dipeptidiques de l'espertam et procédé pour leur préparation, comme aussi une nouvelle préparation de l'espertam
EP0768384A1 (fr) * 1995-10-11 1997-04-16 Holland Sweetener Company V.o.F. Réaction améliorée de couplage enzymatique d'acide L-aspartique N-protégé et d'ester méthylique de phenylalanine
US5693485A (en) * 1995-10-11 1997-12-02 Holland Sweetener Company V.O.F. Enzymatic coupling reaction of N-protected-L-aspartic acid and phenylalanine methyl ester
WO1998016546A1 (fr) * 1996-10-15 1998-04-23 Holland Sweetener Company V.O.F. METHODE ENZYMATIQUE POUR PRODUIRE DU N-FORMYL-α-L-ASPARTYL-L-PHENYLALANINE METHYL ESTER

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3375381D1 (en) * 1982-04-19 1988-02-25 Nissan Motor Method and apparatus for controlling reduction ratio of continuously variable transmission
JPH0724587B2 (ja) * 1982-07-08 1995-03-22 三井東圧化学株式会社 酵素を利用した反応方法
JPS5917997A (ja) * 1982-07-23 1984-01-30 Toyo Soda Mfg Co Ltd ジペプチドエステルとアミノ酸エステルとの付加化合物の製造方法
DE3479214D1 (en) * 1983-04-28 1989-09-07 Ajinomoto Kk Process for the production of l-aspartyl-l-phenylalanine methyl ester or l-aspartyl-l-phenylalanine
WO1986004924A1 (fr) * 1985-02-15 1986-08-28 Vsesojuzny Nauchno-Issledovatelsky Institut Geneti Procede de preparation de n-formyl-l-peptides
US4873359A (en) * 1985-10-21 1989-10-10 W. R. Grace & Co. - Conn. Process for preparing as partyl-phenylalanine dipeptides
US4810817A (en) * 1985-10-21 1989-03-07 W. R. Grace & Co. Aspartyl-beta substituted phenylalanine dipeptides
US4935355A (en) * 1986-04-15 1990-06-19 Synthetech, Inc. Preparation of dipeptides
US4892820A (en) * 1987-06-10 1990-01-09 The Nutrasweet Company Solvent system for enzymatic coupling process
JPH0279993A (ja) * 1987-12-11 1990-03-20 Fan Shun Mou Ii Yuu Shen Kun Tsu Ｌ，ｌ−ジペプチドアスパルテームの製法
DE68924196T2 (de) * 1988-06-03 1996-05-09 Sharp Kk Elektronische Anordnung mit einer Kalenderfunktion.
US5002872A (en) * 1989-05-10 1991-03-26 W. R. Grace & Co.-Conn. Enzyme mediated coupling reactions
KR930002966B1 (ko) * 1990-11-24 1993-04-16 주식회사 미 원 디펩티드의 제조방법
DE4408534A1 (de) * 1994-03-14 1995-09-28 Hoechst Ag Substituierte N-Ethyl-Glycinderivate zur Herstellung von PNA und PNA-/DNA-Hybriden
US6465650B1 (en) 1995-03-13 2002-10-15 Aventis Pharma Deutschland Gmbh Substituted N-ethylglycine derivatives for preparing PNA and PNA/DNA hybrids
CA2172022A1 (fr) * 1995-03-20 1996-09-21 Tsugio Murakami Methode pour cristalliser un ester methylique d'alpha-l-aspartyl-l-phenylalanine
PL194958B1 (pl) * 1998-06-05 2007-07-31 Wrigley W M Jun Co Sposób wytwarzania gumy do żucia zawierającej fizycznie zmodyfikowaną N-podstawioną pochodną aspartamu o kontrolowanej szybkości uwalniania
US6692778B2 (en) * 1998-06-05 2004-02-17 Wm. Wrigley Jr. Company Method of controlling release of N-substituted derivatives of aspartame in chewing gum
CN112301081B (zh) * 2020-10-26 2022-07-22 江南大学 一种酶催化合成苯丙氨酸寡肽-赖氨酸寡肽共聚物的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3972773A (en) * 1975-04-29 1976-08-03 Sagami Chemical Research Center Process for producing peptide
FR2378747A1 (fr) * 1977-01-27 1978-08-25 Toyo Soda Mfg Co Ltd Nouveaux composes d'addition d'un derive de dipeptide et d'un derive d'amino-acide, et leur procede de preparation et de decomposition
US4119493A (en) * 1975-10-23 1978-10-10 (Zaidanhojin) Sagami Chemical Research Center Process for producing a peptide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3972773A (en) * 1975-04-29 1976-08-03 Sagami Chemical Research Center Process for producing peptide
US4119493A (en) * 1975-10-23 1978-10-10 (Zaidanhojin) Sagami Chemical Research Center Process for producing a peptide
FR2378747A1 (fr) * 1977-01-27 1978-08-25 Toyo Soda Mfg Co Ltd Nouveaux composes d'addition d'un derive de dipeptide et d'un derive d'amino-acide, et leur procede de preparation et de decomposition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TETRAHEDRON LETTERS, no. 28, juillet 1979, OXFORD (GB); Y. ISOWA et al.:"The thermolysin-catalyzed condensation reactions of N-substituted aspartic and glutamic acids with phenylalanine alkyl esters". *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2499098A1 (fr) * 1981-02-02 1982-08-06 Searle & Co Procede pour la production d'un ester d'alkyle de (l-aspartyl amino-protege)-l-phenylalanine
EP0074095A1 (fr) * 1981-09-05 1983-03-16 Toyo Soda Manufacturing Co., Ltd. Procédé de préparation d'esters alcoyliques de l'aspartylphénylalanine
EP0086053A1 (fr) * 1982-01-26 1983-08-17 Imahori Kazutomo Procédé de synthèse de peptides ou de dérivés peptidiques
EP0574028A1 (fr) * 1985-10-21 1993-12-15 Hampshire Chemical Corp. Analoques dipeptidiques de l'espertam et procédé pour leur préparation, comme aussi une nouvelle préparation de l'espertam
FR2589480A1 (fr) * 1985-11-05 1987-05-07 Hoechst France Procede biologique de preparation de n-(n-benzyloxycarbonyl l-aspartyl-1) l-phenylalaninate de methyle
EP0227506A1 (fr) * 1985-11-05 1987-07-01 SOCIETE FRANCAISE HOECHST Société anonyme dite: Procédé biologique de préparation de N-(N-benzyloxycarbonyl L-aspartyl-1) L-phénylalaninate de méthyle
EP0269390A2 (fr) * 1986-11-21 1988-06-01 Genencor International, Inc. Production enzymatique de l'ester alcoylique de L-aspartyl-L-phénylalanine
EP0269390A3 (en) * 1986-11-21 1989-04-19 Genencor, Inc. Enzymatic l-aspartyl-l-phenylalanine alkyl ester production
EP0768384A1 (fr) * 1995-10-11 1997-04-16 Holland Sweetener Company V.o.F. Réaction améliorée de couplage enzymatique d'acide L-aspartique N-protégé et d'ester méthylique de phenylalanine
US5693485A (en) * 1995-10-11 1997-12-02 Holland Sweetener Company V.O.F. Enzymatic coupling reaction of N-protected-L-aspartic acid and phenylalanine methyl ester
WO1998016546A1 (fr) * 1996-10-15 1998-04-23 Holland Sweetener Company V.O.F. METHODE ENZYMATIQUE POUR PRODUIRE DU N-FORMYL-α-L-ASPARTYL-L-PHENYLALANINE METHYL ESTER

Also Published As

Publication number Publication date
CH645341A5 (de) 1984-09-28
US4284721A (en) 1981-08-18
GB2049703B (en) 1983-01-12
GB2049703A (en) 1980-12-31
BE882603A (fr) 1980-10-02
IT1147338B (it) 1986-11-19
DE3012693A1 (de) 1980-10-16
DE3012693C2 (fr) 1990-04-26
FR2453137B1 (fr) 1985-06-07
JPS55135595A (en) 1980-10-22
IT8021154A0 (it) 1980-04-02
CA1133841A (fr) 1982-10-19
JPS615399B2 (fr) 1986-02-18
NL8001902A (nl) 1980-10-07

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