WO1987004713A3 - Procede de controle de la synthese d'une combinaison lineaire de residus d'acide amines - Google Patents

Procede de controle de la synthese d'une combinaison lineaire de residus d'acide amines Download PDF

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Publication number
WO1987004713A3
WO1987004713A3 PCT/GB1987/000078 GB8700078W WO8704713A3 WO 1987004713 A3 WO1987004713 A3 WO 1987004713A3 GB 8700078 W GB8700078 W GB 8700078W WO 8704713 A3 WO8704713 A3 WO 8704713A3
Authority
WO
WIPO (PCT)
Prior art keywords
alpha
synthesis
pct
amino acid
amino
Prior art date
Application number
PCT/GB1987/000078
Other languages
English (en)
Other versions
WO1987004713A2 (fr
Inventor
Robert Sheppard
Morten Meldahl
Original Assignee
Medical Res Council
Robert Sheppard
Morten Meldahl
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 Medical Res Council, Robert Sheppard, Morten Meldahl filed Critical Medical Res Council
Priority to AT87901087T priority Critical patent/ATE66003T1/de
Priority to DE8787901087T priority patent/DE3771959D1/de
Publication of WO1987004713A2 publication Critical patent/WO1987004713A2/fr
Priority to DK518587A priority patent/DK518587D0/da
Priority to NO874149A priority patent/NO874149L/no
Priority to FI874330A priority patent/FI874330A/fi
Publication of WO1987004713A3 publication Critical patent/WO1987004713A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
    • C07K1/08—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using activating agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Peptides Or Proteins (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Cephalosporin Compounds (AREA)
  • Polyamides (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

Abstract

Le procédé de contrôle ci-décrit s'applique particulièrement (mais non exclusivement) à la synthèse de peptides en phase solide. Dans un des aspects de la présente invention, la synthèse commence avec un résidu d'acide aminé protégé par un groupe protecteur N-alpha-amino et consiste à: (a) éliminer le groupe protecteur N-alpha-amino afin d'obtenir un groupe N-alpha-amino, (b) ajouter, à l'aide d'une liaison peptide, un résidu d'acide aminé protégé par un groupe protecteur N-alpha-amino au groupe N-alpha-amino obtenu en (a), en utilisant un dérivé d'acide aminé réactif protégé et si nécessaire un catalyseur, et (c) répéter les opérations (a) et (b) jusqu'à obtenir la combinaison linéaire désirée. Le système de réaction comprend un groupe 3-hydroxy-1,2,3-benzotriazine-4(3H)-one ou un dérivé dudit groupe. La couleur du système de réaction ou d'un composant dudit système est contrôlée durant la sysnthèse. Le solvant est de préférence un solvant aprotique polaire, par exemple un diméthylformamide. Lorsque la synthèse est une synthèse en phase solide, la phase solide est de préférence un polyamide. La présente invention décrit également un appareil permettant de mettre en oeuvre lesdits procédés. Dans un mode de réalisation préféré, ledit appareil comprend (i) une colonne destinée à recevoir des particules comprenant une résine de polyamide sur laquelle est effectuée la synthèse en phase solide, (ii) une source de lumière placée sur un des côtés de ladite colonne, (iii) un dispositif de focalisation placé adjacent à ladite colonne et à l'opposé de ladite source de lumière, (iv) un photomètre placé de manière à recevoir la lumière focalisée par ledit dispositif de focalisation, et (v) un microprocesseur programmé pour réagir en fonction de la sortie dudit photodétecteur, de manière à commander la procédure de synthèse.
PCT/GB1987/000078 1986-02-03 1987-02-03 Procede de controle de la synthese d'une combinaison lineaire de residus d'acide amines WO1987004713A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AT87901087T ATE66003T1 (de) 1986-02-03 1987-02-03 Regelung der herstellung einer linearer kombination von aminosaeureresten.
DE8787901087T DE3771959D1 (de) 1986-02-03 1987-02-03 Regelung der herstellung einer linearer kombination von aminosaeureresten.
DK518587A DK518587D0 (da) 1986-02-03 1987-10-02 Fremgangsmaade til at foelge syntesen af en lineaer kombination af aminosyrerester
NO874149A NO874149L (no) 1986-02-03 1987-10-02 Fremgangsmaate ved overvaaking av lineaer syntese av aminosyreresidier.
FI874330A FI874330A (fi) 1986-02-03 1987-10-02 Foerfarande foer oevervakning av framstaellningen av en lineaer kombination av aminosyrarester.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB08602586A GB2187461A (en) 1986-02-03 1986-02-03 Monitoring method for the synthesis of a linear of amino acid residues
GB8602586 1986-02-03

Publications (2)

Publication Number Publication Date
WO1987004713A2 WO1987004713A2 (fr) 1987-08-13
WO1987004713A3 true WO1987004713A3 (fr) 1987-11-05

Family

ID=10592426

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1987/000078 WO1987004713A2 (fr) 1986-02-03 1987-02-03 Procede de controle de la synthese d'une combinaison lineaire de residus d'acide amines

Country Status (11)

Country Link
US (1) US5126273A (fr)
EP (1) EP0257053B1 (fr)
JP (1) JPS63502694A (fr)
AT (1) ATE66003T1 (fr)
AU (1) AU597031B2 (fr)
DE (1) DE3771959D1 (fr)
DK (1) DK518587D0 (fr)
FI (1) FI874330A (fr)
GB (1) GB2187461A (fr)
NO (1) NO874149L (fr)
WO (1) WO1987004713A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3618218A1 (de) * 1986-05-30 1987-12-03 Hoechst Ag Aminosaeure-oobt-ester, verfahren zu deren herstellung und deren verwendung
US5233044A (en) * 1989-06-08 1993-08-03 Millipore Corporation Active esters for solid phase peptide synthesis
SE8902842D0 (sv) * 1989-08-28 1989-08-28 Pharmacia Ab A method for monitoring in peptide synthesis
AU6456496A (en) * 1995-08-17 1997-03-12 Hybridon, Inc. Apparatus and process for multi-stage solid-phase synthesis of long-chained organic molecules
US5807525A (en) * 1995-08-17 1998-09-15 Hybridon, Inc. Apparatus and process for multi stage solid phase synthesis of long chained organic molecules
ES2295961T3 (es) * 2003-12-31 2008-04-16 F. Hoffmann-La Roche Ag Proceso para la sintesis peptidica utilizacndo una cantidad reducida de agente de desproteccion.

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3795666A (en) * 1969-08-01 1974-03-05 Hoechst Ag Method of synthesizing peptides in the presence of a carbodiimide and of 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine
US3872074A (en) * 1972-01-20 1975-03-18 Hoechst Ag Method for the aminolysis of activated esters in the presence of N-hydroxy compounds as catalysts
US4192798A (en) * 1978-11-20 1980-03-11 Bioresearch, Inc. Rapid, large scale, automatable high pressure peptide synthesis
EP0014911A2 (fr) * 1979-02-14 1980-09-03 Hoechst Aktiengesellschaft Dipeptide (pyro)Glu-His(Dnp)-OH et procédé de préparation du facteur LH-RH et des analogues de ce facteur à l'aide dudit dipeptide
US4242507A (en) * 1978-02-23 1980-12-30 Fujisawa Pharmaceutical Co., Ltd. Sulfonic acid esters
EP0064714A1 (fr) * 1981-05-07 1982-11-17 Hoechst Aktiengesellschaft Procédé de phlegmatisation d'hydroxy-oxo-benzotriazoles et d'hydroxy-oxo-benzotriazines
EP0097994A2 (fr) * 1982-06-24 1984-01-11 ENICHEM S.p.A. Méthode pour la synthèse de polypeptides rétro-inverso en phase solide
WO1986003494A1 (fr) * 1984-12-11 1986-06-19 Lkb Biochrom Limited Procede de synthese en phase solide d'une combinaison lineaire de residus d'acides amines
EP0224844A2 (fr) * 1985-11-30 1987-06-10 Hoechst Aktiengesellschaft Procédé de préparation des peptides à l'aide de perchlorates

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH551948A (de) * 1969-04-05 1974-07-31 Hoechst Ag Verfahren zur herstellung von peptiden.
US4105602A (en) * 1975-02-10 1978-08-08 Armour Pharmaceutical Company Synthesis of peptides with parathyroid hormone activity
US4108846A (en) * 1977-02-01 1978-08-22 Hoffmann-La Roche Inc. Solid phase synthesis with base N alpha-protecting group cleavage
DE2830442A1 (de) * 1978-07-11 1980-01-24 Max Planck Gesellschaft Verfahren zur herstellung von polypeptiden
US4701304A (en) * 1985-04-19 1987-10-20 Applied Protein Technologies, Inc. Apparatus for automated synthesis of peptides
US4755558A (en) * 1986-05-30 1988-07-05 Beckman Instruments, Inc. Using internal marker

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3795666A (en) * 1969-08-01 1974-03-05 Hoechst Ag Method of synthesizing peptides in the presence of a carbodiimide and of 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine
US3872074A (en) * 1972-01-20 1975-03-18 Hoechst Ag Method for the aminolysis of activated esters in the presence of N-hydroxy compounds as catalysts
US4242507A (en) * 1978-02-23 1980-12-30 Fujisawa Pharmaceutical Co., Ltd. Sulfonic acid esters
US4192798A (en) * 1978-11-20 1980-03-11 Bioresearch, Inc. Rapid, large scale, automatable high pressure peptide synthesis
EP0014911A2 (fr) * 1979-02-14 1980-09-03 Hoechst Aktiengesellschaft Dipeptide (pyro)Glu-His(Dnp)-OH et procédé de préparation du facteur LH-RH et des analogues de ce facteur à l'aide dudit dipeptide
EP0064714A1 (fr) * 1981-05-07 1982-11-17 Hoechst Aktiengesellschaft Procédé de phlegmatisation d'hydroxy-oxo-benzotriazoles et d'hydroxy-oxo-benzotriazines
EP0097994A2 (fr) * 1982-06-24 1984-01-11 ENICHEM S.p.A. Méthode pour la synthèse de polypeptides rétro-inverso en phase solide
WO1986003494A1 (fr) * 1984-12-11 1986-06-19 Lkb Biochrom Limited Procede de synthese en phase solide d'une combinaison lineaire de residus d'acides amines
EP0224844A2 (fr) * 1985-11-30 1987-06-10 Hoechst Aktiengesellschaft Procédé de préparation des peptides à l'aide de perchlorates

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Volume 88, 1978, (Columbus, Ohio, US), V. TEETZ et al.: "Synthesis and Biological Properties of (B1-3,5-Diiodo-Tyrosine)-Insulin", see page 612, Abstract 105748v *
CHEMICAL ABSTRACTS, Volume 98, 1983, (Columbus, Ohio, US), H. WISSMANN et al.: "Peptide Synthesis using Propylphosphonic Acid Anhydride as Coupling Reagent", see page 726, Abstract 54439s, & Pept., Proc. Eur. Pept. Symp., 16th 1980 (Pub. 1981), 174-9 *
Chemische Beriche, Volume 103, 1970, W. KONIG et al.: "Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid und 3-Hydroxy-4-Oxo-3,4-Dihydro-1.2.3-Benzotriazin" pages 2034-2040 see the whole document cited in the application *

Also Published As

Publication number Publication date
DK518587A (da) 1987-10-02
JPS63502694A (ja) 1988-10-06
EP0257053A1 (fr) 1988-03-02
AU6930387A (en) 1987-08-25
DK518587D0 (da) 1987-10-02
FI874330A0 (fi) 1987-10-02
ATE66003T1 (de) 1991-08-15
AU597031B2 (en) 1990-05-24
GB8602586D0 (en) 1986-03-12
WO1987004713A2 (fr) 1987-08-13
US5126273A (en) 1992-06-30
DE3771959D1 (de) 1991-09-12
GB2187461A (en) 1987-09-09
FI874330A (fi) 1987-10-02
NO874149L (no) 1987-12-03
EP0257053B1 (fr) 1991-08-07
NO874149D0 (no) 1987-10-02

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