WO1992001938A1 - Derivatisation de proline a terminaison c - Google Patents

Derivatisation de proline a terminaison c Download PDF

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Publication number
WO1992001938A1
WO1992001938A1 PCT/US1990/004088 US9004088W WO9201938A1 WO 1992001938 A1 WO1992001938 A1 WO 1992001938A1 US 9004088 W US9004088 W US 9004088W WO 9201938 A1 WO9201938 A1 WO 9201938A1
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WO
WIPO (PCT)
Prior art keywords
reagents
reagent
derivatization
proline
peptide
Prior art date
Application number
PCT/US1990/004088
Other languages
English (en)
Inventor
Chad G. Miller
Original Assignee
City Of Hope
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 City Of Hope filed Critical City Of Hope
Priority to PCT/US1990/004088 priority Critical patent/WO1992001938A1/fr
Publication of WO1992001938A1 publication Critical patent/WO1992001938A1/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
    • C07K1/06—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
    • C07K1/063—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 alpha-amino functions
    • 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
    • C07K1/12—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by hydrolysis, i.e. solvolysis in general
    • C07K1/128—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by hydrolysis, i.e. solvolysis in general sequencing
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
    • G01N33/6818—Sequencing of polypeptides
    • G01N33/6821—Sequencing of polypeptides involving C-terminal degradation

Definitions

  • This invention relates to reagents useful to derivatize C-terminal proline residues of peptides. More particularly, the invention relates to reagents which react with the mixed anhydride reaction product of a peptide having a C-terminal proline residue and acetic anhydride.
  • the reagents of the invention comprise a class of compounds having a 3-amino-2-halo pyridine structure. Such compounds function as nucleophilic reagents with respect to acetic acid anhydride activated proline residues. Under appropriate conditions the amide nitrogen of the proline residue may displace the halogen of the reagent to provide a cleavable cyclic derivative.
  • the reagents of the invention thus accommodate C-terminal sequencing of prolyl containing peptides.
  • the reagents useful in the invention have the structural formula I
  • x is a halogen, preferably chlorine or fluorine and y, if present, is an alkyl group, preferably having from about one to about six carbon atoms or an oxide (O-) .
  • a peptide having a terminal proline residue is reacted with acetic anhydride in known manner (see, e.g. , co-pending U.S. Patent Application Serial No. 07/311,966) to provide a linear mixed anhydride which has one component of the generic formula II
  • Cyclization may be facilitated by the use of 3 amino-2-fluoropyridine to provide a fluorine atom as a leaving group.
  • the ring nitrogen of the pyridine moiety of the peptide addition product may be methylated, e.g., by reaction with methyl iodide to enhance the ability of the halo substituent of the reagent to function as a leaving group.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Physics & Mathematics (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Genetics & Genomics (AREA)
  • Cell Biology (AREA)
  • Biotechnology (AREA)
  • Bioinformatics & Computational Biology (AREA)
  • Microbiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Food Science & Technology (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Procédé permettant de faire réagir un produit de réaction linéaire anhydride mélangé d'un peptide et un anhydride acétique avec un réactif. Cette invention décrit des réactifs utiles pour la dérivatisation de peptides contenant du prolyle. Les réactifs de cette invention comprennent une classe de composés ayant une structure halo pyridine 3-amino-2. De tels composés fonctionnent comme des réactifs nucléophiles par rapport aux restes de proline activée par l'anhydride d'acide acétique. Dans des conditions appropriées, l'azote amide du reste de proline peut déplacer l'halogène du réactif pour donner un dérivé cyclique clivable. Les réactifs de cette invention adaptent donc la mise en séquence de la terminaison C des peptides contenant du propyle.
PCT/US1990/004088 1990-07-20 1990-07-20 Derivatisation de proline a terminaison c WO1992001938A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US1990/004088 WO1992001938A1 (fr) 1990-07-20 1990-07-20 Derivatisation de proline a terminaison c

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1990/004088 WO1992001938A1 (fr) 1990-07-20 1990-07-20 Derivatisation de proline a terminaison c

Publications (1)

Publication Number Publication Date
WO1992001938A1 true WO1992001938A1 (fr) 1992-02-06

Family

ID=22220964

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1990/004088 WO1992001938A1 (fr) 1990-07-20 1990-07-20 Derivatisation de proline a terminaison c

Country Status (1)

Country Link
WO (1) WO1992001938A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7244851B2 (en) 2004-07-02 2007-07-17 Genentech, Inc. Inhibitors of IAP
US7345081B2 (en) 2004-03-23 2008-03-18 Genentech, Inc. Azabicyclo-octane inhibitors of IAP
US8063218B2 (en) 2006-12-19 2011-11-22 Genentech, Inc. Imidazopyridine inhibitors of IAP
US8247557B2 (en) 2005-12-19 2012-08-21 Genentech, Inc. IAP inhibitors
US8609845B2 (en) 2004-12-20 2013-12-17 Genentech, Inc. Pyrrolidine inhibitors of IAP
WO2014010732A1 (fr) 2012-07-13 2014-01-16 武田薬品工業株式会社 Composé hétérocyclique
US8835393B2 (en) 2008-08-02 2014-09-16 Genentech, Inc. Inhibitors of IAP
US8907092B2 (en) 2007-04-30 2014-12-09 Genentech, Inc. Inhibitors of IAP
US9469637B2 (en) 2012-04-25 2016-10-18 Takeda Pharmaceutical Company Limited Nitrogenated heterocyclic compound
US9834520B2 (en) 2013-03-14 2017-12-05 Takeda Pharmaceutical Company Limited Heterocyclic compound
US10053468B2 (en) 2013-07-03 2018-08-21 Takeda Pharmaceutical Company Limited Heterocyclic compound
US10472376B2 (en) 2013-07-03 2019-11-12 Takeda Pharmaceutical Company Limited Amide compound

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4149003A (en) * 1977-03-04 1979-04-10 Pharmacia Fine Chemicals Ab Pyridine disulfide compounds
US4837165A (en) * 1985-09-26 1989-06-06 Beckman Research Institute, City Of Hope Method for sequencing of peptides by carboxyl terminus degradation
US4935494A (en) * 1988-11-15 1990-06-19 City Of Hope C-terminal peptide and protein sequencing

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4149003A (en) * 1977-03-04 1979-04-10 Pharmacia Fine Chemicals Ab Pyridine disulfide compounds
US4837165A (en) * 1985-09-26 1989-06-06 Beckman Research Institute, City Of Hope Method for sequencing of peptides by carboxyl terminus degradation
US4935494A (en) * 1988-11-15 1990-06-19 City Of Hope C-terminal peptide and protein sequencing

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BIOCHEMISTRY, Vol. 7, No. 5, issued May 1968, "Sequential Degradation of peptides from their Carboxyl Termini with Ammonium Thiocyanate and Acetic Anhydride", STARK, see pages 1796-1807. *

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7345081B2 (en) 2004-03-23 2008-03-18 Genentech, Inc. Azabicyclo-octane inhibitors of IAP
US8980837B2 (en) 2004-07-02 2015-03-17 Genentech, Inc. Inhibitors of IAP
US7244851B2 (en) 2004-07-02 2007-07-17 Genentech, Inc. Inhibitors of IAP
US8110568B2 (en) 2004-07-02 2012-02-07 Genentech, Inc. Inhibitors of IAP
US9040706B2 (en) 2004-12-20 2015-05-26 Genentech, Inc. Pyrrolidine inhibitors of IAP
US8609845B2 (en) 2004-12-20 2013-12-17 Genentech, Inc. Pyrrolidine inhibitors of IAP
US8247557B2 (en) 2005-12-19 2012-08-21 Genentech, Inc. IAP inhibitors
US8063218B2 (en) 2006-12-19 2011-11-22 Genentech, Inc. Imidazopyridine inhibitors of IAP
US8907092B2 (en) 2007-04-30 2014-12-09 Genentech, Inc. Inhibitors of IAP
US8835393B2 (en) 2008-08-02 2014-09-16 Genentech, Inc. Inhibitors of IAP
US9469637B2 (en) 2012-04-25 2016-10-18 Takeda Pharmaceutical Company Limited Nitrogenated heterocyclic compound
US10017508B2 (en) 2012-04-25 2018-07-10 Takeda Pharmaceutical Company Limited Nitrogenated heterocyclic compound
JPWO2014010732A1 (ja) * 2012-07-13 2016-06-23 武田薬品工業株式会社 複素環化合物
US9527841B2 (en) 2012-07-13 2016-12-27 Takeda Pharmaceutical Company Limited Substituted pyrido[2,3-b]pyrazines as phosphodiesterase 2A inhibitors
WO2014010732A1 (fr) 2012-07-13 2014-01-16 武田薬品工業株式会社 Composé hétérocyclique
US9834520B2 (en) 2013-03-14 2017-12-05 Takeda Pharmaceutical Company Limited Heterocyclic compound
US10053468B2 (en) 2013-07-03 2018-08-21 Takeda Pharmaceutical Company Limited Heterocyclic compound
US10472376B2 (en) 2013-07-03 2019-11-12 Takeda Pharmaceutical Company Limited Amide compound
US11053262B2 (en) 2013-07-03 2021-07-06 Takeda Pharmaceutical Company Limited Heterocyclic amide compounds having RORyT inhibitory action
US11851449B2 (en) 2013-07-03 2023-12-26 Takeda Pharmaceutical Company Limited Heterocyclic amide compounds having an RORvt inhibitory action

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