WO2003093301A3 - Procede permettant de synthetiser des peptides - Google Patents

Procede permettant de synthetiser des peptides Download PDF

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Publication number
WO2003093301A3
WO2003093301A3 PCT/GB2003/001925 GB0301925W WO03093301A3 WO 2003093301 A3 WO2003093301 A3 WO 2003093301A3 GB 0301925 W GB0301925 W GB 0301925W WO 03093301 A3 WO03093301 A3 WO 03093301A3
Authority
WO
WIPO (PCT)
Prior art keywords
nitrogen
solid
amino acid
synthesis
peptides
Prior art date
Application number
PCT/GB2003/001925
Other languages
English (en)
Other versions
WO2003093301A2 (fr
Inventor
David John Evans
Eric Atherton
Original Assignee
Avecia Ltd
David John Evans
Eric Atherton
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 Avecia Ltd, David John Evans, Eric Atherton filed Critical Avecia Ltd
Priority to AU2003224327A priority Critical patent/AU2003224327A1/en
Publication of WO2003093301A2 publication Critical patent/WO2003093301A2/fr
Publication of WO2003093301A3 publication Critical patent/WO2003093301A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
    • 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
    • C07K1/003—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by transforming the C-terminal amino acid to amides
    • 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
    • C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
    • C07K1/042—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers characterised by the nature of the carrier
    • 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
    • C07K1/061—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 protecting groups
    • C07K1/067—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 protecting groups for sulfur-containing functions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/64—Cyclic peptides containing only normal peptide links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • 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)
  • 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)
  • Analytical Chemistry (AREA)
  • Peptides Or Proteins (AREA)

Abstract

L'invention concerne un procédé permettant de réaliser la synthèse en phase solide d'un peptide qui consiste à fixer un acide aminé à α-azote et à α-carboxy protégé sur un support solide via sa chaîne latérale, à supprimer le groupe protecteur de α-azote et à assembler une chaîne peptidique sur ledit α-azote. L'invention concerne également de nouveaux analogues d'acide aminé et des supports en phase solide.
PCT/GB2003/001925 2002-05-03 2003-05-02 Procede permettant de synthetiser des peptides WO2003093301A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003224327A AU2003224327A1 (en) 2002-05-03 2003-05-02 Process for the synthesis of peptides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0210183.0 2002-05-03
GBGB0210183.0A GB0210183D0 (en) 2002-05-03 2002-05-03 Process

Publications (2)

Publication Number Publication Date
WO2003093301A2 WO2003093301A2 (fr) 2003-11-13
WO2003093301A3 true WO2003093301A3 (fr) 2004-01-08

Family

ID=9936029

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2003/001925 WO2003093301A2 (fr) 2002-05-03 2003-05-02 Procede permettant de synthetiser des peptides

Country Status (3)

Country Link
AU (1) AU2003224327A1 (fr)
GB (1) GB0210183D0 (fr)
WO (1) WO2003093301A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE602006011099D1 (de) * 2005-05-03 2010-01-28 Novetide Ltd Verfahren zur herstellung von peptidderivaten
CN101628929B (zh) * 2009-08-27 2014-09-17 中国人民解放军防化学院 一种固相合成侧链保护肽链的新方法
MX365465B (es) 2013-03-21 2019-06-04 Sanofi Aventis Deutschland Sintesis de productos peptidicos que contienen imida ciclica.
SG11201506804VA (en) 2013-03-21 2015-09-29 Sanofi Aventis Deutschland Synthesis of hydantoin containing peptide products

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0519327A1 (fr) * 1991-06-17 1992-12-23 Hoechst Aktiengesellschaft N-Acyl-S-(2-hydroxyalkyl)-cystéines, leur préparation et leur emploi comme intermédiaires dans la préparation de immuno-adjuvants synthétiques et vaccins synthétiques
US6008058A (en) * 1993-06-18 1999-12-28 University Of Louisville Cyclic peptide mixtures via side chain or backbone attachment and solid phase synthesis

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0519327A1 (fr) * 1991-06-17 1992-12-23 Hoechst Aktiengesellschaft N-Acyl-S-(2-hydroxyalkyl)-cystéines, leur préparation et leur emploi comme intermédiaires dans la préparation de immuno-adjuvants synthétiques et vaccins synthétiques
US6008058A (en) * 1993-06-18 1999-12-28 University Of Louisville Cyclic peptide mixtures via side chain or backbone attachment and solid phase synthesis

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
A BERNHARDT ET AL.: "The sold-phase synthesis of side-chain-phoshorylated peptide-4-nitroanilides", JOURNAL OF PEPTIDE RESEARCH., vol. 50, no. 8, August 1997 (1997-08-01), MUNKSGAARD INTERNATIONAL PUBLISHERS, COPENHAGEN., DK, pages 143 - 152, XP000659212, ISSN: 1397-002X *
A F SPATOLA ET AL.: "An approach to cyclic peptide libraries: reducing epimerization in medium sized rings during solid phase synthesis", TETRAHEDRON LETTERS., vol. 37, no. 5, 1996, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 591 - 594, XP004030307, ISSN: 0040-4039 *
C CABRELE ET AL.: "Amino acid side chain attachment approach and its application to the synthesis of tyrosine-containing cyclic peptides", JOURNAL OF ORGANIC CHEMISTRY., vol. 64, no. 12, 1999, AMERICAN CHEMICAL SOCIETY. EASTON., US, pages 4353 - 4361, XP002258925, ISSN: 0022-3263 *
CABRELE, CHIARA ET AL: "Amino acid side chain attachment: a convenient strategy to obtain C-terminally modified or cyclic peptides by solid phase synthesis", PEPTIDES 1998, PROCEEDINGS OF THE EUROPEAN PEPTIDE SYMPOSIUM, 25TH, BUDAPEST, AUG. 30-SEPT. 4, 1998 (1999), MEETING DATE 1998, 202-203. EDITOR(S): BAJUSZ, SANDOR;HUDECZ, FERENC. PUBLISHER: AKADEMIAI KIADO, BUDAPEST, HUNG., 1999, XP002258926 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; HAN, YONGXIN ET AL: "A new side-chain anchoring strategy for solid-phase synthesis of peptide acids with C-terminal cysteine", XP002258927, retrieved from STN Database accession no. 127:50990 CA *
H M ZHONG ET AL.: "Solid-phase synthesis of arginine-containing peptides by guanidine attachment to a sulfonyl linker", JOURNAL OF ORGANIC CHEMISTRY., vol. 62, no. 26, 1997, AMERICAN CHEMICAL SOCIETY. EASTON., US, pages 9326 - 9330, XP002258924, ISSN: 0022-3263 *
INNOVATION AND PERSPECTIVES IN SOLID PHASE SYNTHESIS & COMBINATORIAL LIBRARIES: PEPTIDES, PROTEINS AND NUCLEIC ACIDS--SMALL MOLECULE ORGANIC CHEMICAL DIVERSITY, COLLECTED PAPERS, INTERNATIONAL SYMPOSIUM, 4TH, EDINBURGH, SEPT. 12-16, 1995 (1996), MEET, 1996 *
J ALSINA ET AL.: "Active carbonate resins for solid-phase synthesis through the anchoring of a hydroxyl function. Synthesis of cyclic and alcohol peptides", TETRAHEDRON LETTERS., vol. 38, no. 5, 1997, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 883 - 886, XP004017038, ISSN: 0040-4039 *
P ROMANOVSKIS & A SPATOLA: "Preparation of head-to-tail cyclic peptides via side-chain attachment: implications for library synthesis", JOURNAL OF PEPTIDE RESEARCH., vol. 52, no. 11, November 1998 (1998-11-01), MUNKSGAARD INTERNATIONAL PUBLISHERS, COPENHAGEN., DK, pages 356 - 374, XP000788443, ISSN: 1397-002X *

Also Published As

Publication number Publication date
WO2003093301A2 (fr) 2003-11-13
AU2003224327A1 (en) 2003-11-17
AU2003224327A8 (en) 2003-11-17
GB0210183D0 (en) 2002-06-12

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