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WO1992000284A3 - Procede de formation d'un acide amine thiohydantoïne a l'aide d'un activateur de cetenimine a substitution n - Google Patents

Procede de formation d'un acide amine thiohydantoïne a l'aide d'un activateur de cetenimine a substitution n Download PDF

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Publication number
WO1992000284A3
WO1992000284A3 PCT/US1991/004397 US9104397W WO9200284A3 WO 1992000284 A3 WO1992000284 A3 WO 1992000284A3 US 9104397 W US9104397 W US 9104397W WO 9200284 A3 WO9200284 A3 WO 9200284A3
Authority
WO
WIPO (PCT)
Prior art keywords
amino acid
ketenimine
substituted
forming
activator
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.)
Ceased
Application number
PCT/US1991/004397
Other languages
English (en)
Other versions
WO1992000284A2 (fr
Inventor
Victoria Boyd
David Hawke
Timothy G Geiser
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.)
Applied Biosystems Inc
Original Assignee
Applied Biosystems Inc
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 Applied Biosystems Inc filed Critical Applied Biosystems Inc
Priority to JP3512899A priority Critical patent/JP2989007B2/ja
Priority to DE69130530T priority patent/DE69130530T2/de
Priority to EP91913907A priority patent/EP0536324B1/fr
Publication of WO1992000284A2 publication Critical patent/WO1992000284A2/fr
Publication of WO1992000284A3 publication Critical patent/WO1992000284A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
    • Y10S530/81—Carrier - bound or immobilized peptides or proteins and the preparation thereof, e.g. biological cell or cell fragment as carrier
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/25—Chemistry: analytical and immunological testing including sample preparation
    • Y10T436/25125—Digestion or removing interfering materials
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/25—Chemistry: analytical and immunological testing including sample preparation
    • Y10T436/25375—Liberation or purification of sample or separation of material from a sample [e.g., filtering, centrifuging, etc.]
    • Y10T436/255—Liberation or purification of sample or separation of material from a sample [e.g., filtering, centrifuging, etc.] including use of a solid sorbent, semipermeable membrane, or liquid extraction

Landscapes

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

Abstract

Procédé de formation d'un acide aminé thiohydantoïne à partir d'un acide aminé à protection N ou de l'acide aminé à terminaison C d'un peptide à protection N. L'acide aminé est activé par réaction avec une cétènimine, et l'ester activé est transformé en un thiohydantoïne par réaction avec de l'isothiocyanate de silyle ou de pyridine. La cétènimine est générée par traitement d'un composé isoxazolium à substitution N, tel que le réactif K de Woodwards avec une base, de préférence en présence de l'acide aminé. L'invention concerne également un support à phase solide comportant un groupe isoxazolium ou cétènimine à substitution N transformé en dérivé, destiné à être utilisé dans le procédé.
PCT/US1991/004397 1990-06-29 1991-06-21 Procede de formation d'un acide amine thiohydantoïne a l'aide d'un activateur de cetenimine a substitution n Ceased WO1992000284A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP3512899A JP2989007B2 (ja) 1990-06-29 1991-06-21 Ｎ―置換ケテンイミン活性化物質を用いるアミノ酸チオヒダントインの生成方法
DE69130530T DE69130530T2 (de) 1990-06-29 1991-06-21 Methode zur bildung eines aminosäurehydantoinderivats unter verwendung eines n-substituierten ketenimins als aktivator
EP91913907A EP0536324B1 (fr) 1990-06-29 1991-06-21 Procede de formation d'un acide amine thiohydanto ne a l'aide d'un activateur de cetenimine a substitution n

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/546,303 US5051368A (en) 1990-06-29 1990-06-29 Method for forming an amino acid thiohydantoin using an N-substituted ketenimine activator
US546,303 1990-06-29

Publications (2)

Publication Number Publication Date
WO1992000284A2 WO1992000284A2 (fr) 1992-01-09
WO1992000284A3 true WO1992000284A3 (fr) 1992-04-30

Family

ID=24179804

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1991/004397 Ceased WO1992000284A2 (fr) 1990-06-29 1991-06-21 Procede de formation d'un acide amine thiohydantoïne a l'aide d'un activateur de cetenimine a substitution n

Country Status (6)

Country Link
US (1) US5051368A (fr)
EP (1) EP0536324B1 (fr)
JP (1) JP2989007B2 (fr)
AT (1) ATE173831T1 (fr)
DE (1) DE69130530T2 (fr)
WO (1) WO1992000284A2 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5185266A (en) * 1991-10-15 1993-02-09 Applied Biosystems, Inc. Cleavage method for acyl thiohydantoins and use of the method in c-terminal peptide sequencing
US5304497A (en) * 1991-10-15 1994-04-19 Applied Biosystems, Inc. Method of forming N-protected amino acid thiohydantoins
US5227309A (en) * 1991-10-18 1993-07-13 City Of Hope C-terminal peptide sequencing method
US5602207A (en) * 1993-01-11 1997-02-11 The Perkin-Elmer Corporation Support and method for immobilizing polypeptides
US5665603A (en) * 1993-07-26 1997-09-09 The Perkin-Elmer Corporation Thiohydantoin formation and selective modification of the carboxy terminus of an aspartic acid- and/or glutamic acid-containing protein
US5468843A (en) * 1994-09-08 1995-11-21 Perkin-Elmer Acetic anhydride activation for C-terminal protein sequencing
JP3124507B2 (ja) * 1996-05-24 2001-01-15 セイコーインスツルメンツ株式会社 タンパク質あるいはペプチドのカルボキシ末端からのアミノ酸配列を決定する方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0217634A2 (fr) * 1985-09-26 1987-04-08 Beckman Research Institute of the City of Hope Séquençage de peptides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4289853A (en) * 1977-10-03 1981-09-15 Illinois Water Treatment Company High loading of immobilized enzymes on activated carbon supports
US4935494A (en) * 1988-11-15 1990-06-19 City Of Hope C-terminal peptide and protein sequencing

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0217634A2 (fr) * 1985-09-26 1987-04-08 Beckman Research Institute of the City of Hope Séquençage de peptides

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
Biochim. Biophys. Acta, volume 229, 1971, S. Yamashita: "Sequential degradation of polypeptides from the carboxyl ends. 1. Specific cleavage of the carboxyl-end peptide bonds", pages 301-309, see pages 301-309 *
Intern. Conference on Methods in Protein Sequence Analysis, volume 7, 1988, Springer Verlag (Berlin, DE) A.S. Inglis et al.: "C-terminal sequencing: A new look at the Schlack-Kumpf thiocyanate degradation procedure", see pages 144-151 *
J. Org. Chem. volume 38, no. 25, 1973, D.J. Woodman et al.: "N-acylation during the addition of carboxylic acids to N-tert-butylacylketenimines and the use of the reagent N-tert-butyl-5-metylisoxazolium perchlorate for peptide synthesis", pages 4288-4295, see pages 4288-4295 *
Techniques in Protein Chemistry, C.G. Miller et al.: "Studies on the use of silyl compounds for protein carboxy-terminal sequence analysis", pages 67-78, see pages 67-78 *
Tetrahedron Letters, volume 31, no. 27, 1990, Pergamon Press plc, V.L. Boyd et al.: "Synthesis of the 2-thiohydantoins of amino acids using woodward's reagent K", pages 3849-3852, see pages 3849-3852 *
Tetrahedron Supplement no. 7, 1966, Pergamon Press Ltd, R.B. Woodward et al.: "The reaction of isoxazolium salts with nucleophiles", pages 415-440, see pages 415-440 *
The Journal of the American Chemical Society, volume 83, 1961, R.W. Woodward et al.: "A new synthesis of peptides", see pages 1010-1012 *

Also Published As

Publication number Publication date
WO1992000284A2 (fr) 1992-01-09
JPH05508413A (ja) 1993-11-25
DE69130530D1 (de) 1999-01-07
DE69130530T2 (de) 1999-06-10
US5051368A (en) 1991-09-24
EP0536324B1 (fr) 1998-11-25
ATE173831T1 (de) 1998-12-15
EP0536324A1 (fr) 1993-04-14
JP2989007B2 (ja) 1999-12-13

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