FR2361347A1 - PROCEDURE FOR REMOVING GROUPS PROTECTING THIOL GROUPS PRESENT IN AMINO ACIDS AND PEPTIDES - Google Patents

PROCEDURE FOR REMOVING GROUPS PROTECTING THIOL GROUPS PRESENT IN AMINO ACIDS AND PEPTIDES

Info

Publication number
FR2361347A1
FR2361347A1 FR7719632A FR7719632A FR2361347A1 FR 2361347 A1 FR2361347 A1 FR 2361347A1 FR 7719632 A FR7719632 A FR 7719632A FR 7719632 A FR7719632 A FR 7719632A FR 2361347 A1 FR2361347 A1 FR 2361347A1
Authority
FR
France
Prior art keywords
groups
peptides
amino acids
protecting
thiol groups
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
FR7719632A
Other languages
French (fr)
Other versions
FR2361347B1 (en
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.)
Takeda Pharmaceutical Co Ltd
Original Assignee
Takeda Chemical Industries Ltd
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 Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Publication of FR2361347A1 publication Critical patent/FR2361347A1/en
Application granted granted Critical
Publication of FR2361347B1 publication Critical patent/FR2361347B1/fr
Granted 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
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/655—Somatostatins
    • 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
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • 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
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • 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)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Endocrinology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Toxicology (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procédé pour enlever des groupements protégeant les groupes thiol présents dans des amino-acides et des peptides. On enlève les groupements protecteurs protégeant les groupes thiols d'un amino-acide ou d'un peptide, groupes thiol protégés par les groupements para-méthoxybenzyle, l-adamantyle ou tertio-butyle, en traitant l'amino-acide ou le peptide protégé avec un sel mercurique de l'acide acétique ou d'un acide halogéno-acétique, l'élimination étant effectuée sélectivement et très doucement avec un bon rendement dans des conditions extrêmement douces, sans qu'il y ait une influence quelconque défavorable sur d'autres groupes fonctionnels ou d'autres groupements protecteurs. Utilisation de ce procédé dans la synthèse de peptides.A method of removing groups protecting thiol groups present in amino acids and peptides. The protective groups protecting the thiol groups of an amino acid or a peptide, thiol groups protected by the para-methoxybenzyl, 1-adamantyl or tert-butyl groups, are removed by treating the amino acid or the protected peptide. with a mercuric salt of acetic acid or of a halo-acetic acid, the removal being carried out selectively and very gently with good yield under extremely mild conditions, without there being any adverse influence on any other functional groups or other protecting groups. Use of this process in the synthesis of peptides.

FR7719632A 1976-06-28 1977-06-27 PROCEDURE FOR REMOVING GROUPS PROTECTING THIOL GROUPS PRESENT IN AMINO ACIDS AND PEPTIDES Granted FR2361347A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP51076676A JPS5848524B2 (en) 1976-06-28 1976-06-28 Method for removing thiol protecting group

Publications (2)

Publication Number Publication Date
FR2361347A1 true FR2361347A1 (en) 1978-03-10
FR2361347B1 FR2361347B1 (en) 1980-10-17

Family

ID=13612020

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7719632A Granted FR2361347A1 (en) 1976-06-28 1977-06-27 PROCEDURE FOR REMOVING GROUPS PROTECTING THIOL GROUPS PRESENT IN AMINO ACIDS AND PEPTIDES

Country Status (5)

Country Link
JP (1) JPS5848524B2 (en)
CA (1) CA1074300A (en)
FR (1) FR2361347A1 (en)
GB (1) GB1548101A (en)
HU (1) HU178756B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0017536A2 (en) * 1979-03-23 1980-10-15 Sanofi S.A. Process for the preparation of somatostatine

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62227053A (en) * 1986-03-28 1987-10-06 Sumitomo Special Metals Co Ltd High permeability magnetic alloy excellent in workability
JPS62227054A (en) * 1986-03-28 1987-10-06 Sumitomo Special Metals Co Ltd High permeability magnetic alloy excellent in workability
JPH02111838A (en) * 1988-10-21 1990-04-24 Nippon Steel Corp Fe-ni magnetic alloy excellent in hot workability and magnetic property
JPH04214832A (en) * 1990-07-30 1992-08-05 Nippon Yakin Kogyo Co Ltd Fe high-ni alloy excellent in surface property

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0017536A2 (en) * 1979-03-23 1980-10-15 Sanofi S.A. Process for the preparation of somatostatine
FR2451915A1 (en) * 1979-03-23 1980-10-17 Clin Midy NEW PROCESS FOR THE PREPARATION OF SOMATOSTATIN
EP0017536A3 (en) * 1979-03-23 1981-01-07 Sanofi, Societe Anonyme Process for the preparation of somatostatine, the intermediates and their preparation

Also Published As

Publication number Publication date
HU178756B (en) 1982-06-28
GB1548101A (en) 1979-07-04
JPS5848524B2 (en) 1983-10-28
JPS532404A (en) 1978-01-11
FR2361347B1 (en) 1980-10-17
CA1074300A (en) 1980-03-25

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Legal Events

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