GB1182450A - Process for the Manufacture of Amino Acids and Peptides and the Derivatives Thereof - Google Patents

Process for the Manufacture of Amino Acids and Peptides and the Derivatives Thereof

Info

Publication number
GB1182450A
GB1182450A GB3950767A GB3950767A GB1182450A GB 1182450 A GB1182450 A GB 1182450A GB 3950767 A GB3950767 A GB 3950767A GB 3950767 A GB3950767 A GB 3950767A GB 1182450 A GB1182450 A GB 1182450A
Authority
GB
United Kingdom
Prior art keywords
arg
ser
tyr
gly
glu
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.)
Expired
Application number
GB3950767A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB1182450A publication Critical patent/GB1182450A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
    • C07K14/695—Corticotropin [ACTH]
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Zoology (AREA)
  • Toxicology (AREA)
  • Analytical Chemistry (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,182,450. Process for amino acids and peptides. FARBWERKE HOECHST A.G. 29 Aug., 1967 [27 Aug., 1966; 10 Feb., 1967], No. 39507/67. Heading C2C. In a process for preparing amino acids and polypeptides, an amino acid or polypeptide containing N-formyl groups or derivatives thereof, with the exception of esters with primary or secondary alcohols, are reacted with an at least equimolar amount of a compound R-NH-R<SP>1</SP> in which R is H, alkyl, optionally substituted aralkyl or aryl, alkanoyl, aroyl, alkyl or aralkyl-oxycarbonyl, carbamoyl or thiocarbamoyl or amidino, and R<SP>1</SP> is amino, or (when R is alkyl or aryl), alkylamino or arylamino, or (when R is H), OH or alkoxy or phenyl optionally substituted by alkyl, OH, alkoxy, amino and halogen and when R is H, alkyl or aralkyl and R<SP>1</SP> is amino or alkylamino the reaction is carried out in the presence of a weak organic acid. The following intermediates are prepared: BOC - Sa - Tyr - Sa - Met - Glu(OtBu) - - His - Phe - Arg - Try - Gly - Lys(For) - Pro - Val - Gly - Lys(For) - Lys(For) - Arg - Arg - Pro - Val - Lys (For)- Val-Tyr NH 2 (from the decapeptide and the tridecapeptide); H - Tyr - Ser - Met - Glu(OtBu)- His - Phe - Arg - Try - Gly - OH (from the BOC-blocked peptide) and For-Tyr-Ser-Met- Glu(OtBu) - His - Phe - Arg - Try - Gly - OH; Ac - Ser - Tyr - Ser - Met - Glu(OtBu) - His - Phe - Arg - Try - Gly - Lys(For) - Pro - Val - NH 2 (from the decapeptide and the tripeptide) and Ac - Ser - Tyr - Ser - Met - Glu(OH) - His- Phe - Arg - Try - Gly - Lys(For) - Pro - Val-NH 2 and BOC - D - Ser - Tyr - Ser - Met - Glu(OtBu)- His-Phe-Arg-Try-Gly-OH.
GB3950767A 1966-08-27 1967-08-29 Process for the Manufacture of Amino Acids and Peptides and the Derivatives Thereof Expired GB1182450A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEF0050057 1966-08-27
DEF0051486 1967-02-10

Publications (1)

Publication Number Publication Date
GB1182450A true GB1182450A (en) 1970-02-25

Family

ID=25977383

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3950767A Expired GB1182450A (en) 1966-08-27 1967-08-29 Process for the Manufacture of Amino Acids and Peptides and the Derivatives Thereof

Country Status (4)

Country Link
CH (1) CH491859A (en)
DE (2) DE1543610A1 (en)
GB (1) GB1182450A (en)
NL (1) NL6711728A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2554421A1 (en) * 1974-12-05 1976-06-10 Ajinomoto Kk METHOD OF REMOVING THE FORMYL GROUP OF N-FORMYLAMINO ACID AND N-FORMYL PEPTIDE ESTERS
FR2505829A1 (en) * 1981-05-13 1982-11-19 Pierrel Spa PROCESS FOR THE ELIMINATION OF THE N-FORMYL GROUP OF N-FORMYL PEPTIDES AND ESTERS OF N-FORMYL PEPTIDES
FR2655348A1 (en) * 1989-12-04 1991-06-07 Rhone Poulenc Chimie Reaction and solubilising medium for peptides and process for the synthesis of peptides using this medium
EP0432022A1 (en) * 1989-12-04 1991-06-12 Rhone-Poulenc Chimie Medium for reaction and dissolution of peptides and process of peptide synthesis by making use of said medium
FR2664278A1 (en) * 1990-07-06 1992-01-10 Rhone Poulenc Chimie Reaction and solubilising medium for peptides and process for the synthesis of peptides using this medium

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2554421A1 (en) * 1974-12-05 1976-06-10 Ajinomoto Kk METHOD OF REMOVING THE FORMYL GROUP OF N-FORMYLAMINO ACID AND N-FORMYL PEPTIDE ESTERS
FR2505829A1 (en) * 1981-05-13 1982-11-19 Pierrel Spa PROCESS FOR THE ELIMINATION OF THE N-FORMYL GROUP OF N-FORMYL PEPTIDES AND ESTERS OF N-FORMYL PEPTIDES
DE3216512A1 (en) * 1981-05-13 1982-12-23 Pierrel S.p.A., Napoli METHOD FOR REMOVING THE FORMYL GROUP FROM N-FORMYL PEPTIDES AND ITS ESTERS
FR2655348A1 (en) * 1989-12-04 1991-06-07 Rhone Poulenc Chimie Reaction and solubilising medium for peptides and process for the synthesis of peptides using this medium
EP0432022A1 (en) * 1989-12-04 1991-06-12 Rhone-Poulenc Chimie Medium for reaction and dissolution of peptides and process of peptide synthesis by making use of said medium
US6342582B1 (en) 1989-12-04 2002-01-29 Rhodia Chimie Reaction and dissolving medium for peptides and synthesis method using this medium
FR2664278A1 (en) * 1990-07-06 1992-01-10 Rhone Poulenc Chimie Reaction and solubilising medium for peptides and process for the synthesis of peptides using this medium

Also Published As

Publication number Publication date
NL6711728A (en) 1968-02-28
DE1543610A1 (en) 1969-07-31
CH491859A (en) 1970-06-15
DE1593848A1 (en) 1970-10-29

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees