GB1014426A - Peptides and process for their manufacture - Google Patents

Peptides and process for their manufacture

Info

Publication number
GB1014426A
GB1014426A GB3457362A GB3457362A GB1014426A GB 1014426 A GB1014426 A GB 1014426A GB 3457362 A GB3457362 A GB 3457362A GB 3457362 A GB3457362 A GB 3457362A GB 1014426 A GB1014426 A GB 1014426A
Authority
GB
United Kingdom
Prior art keywords
group
tertiary
phthalyl
pht
lys
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
GB3457362A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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
Priority claimed from CH1059961A external-priority patent/CH437337A/en
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB1014426A publication Critical patent/GB1014426A/en
Expired legal-status Critical Current

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
    • 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
    • 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
    • C07K14/68—Melanocyte-stimulating hormone [MSH]

Landscapes

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

Abstract

The invention comprises an Na -tertiary butyl oxycarbonyl - No - phthalyl - diamino - alkanoic acid; a peptide built up from natural a -amino acids and containing at least one lipine radical, in which the or each e -amino group of lipine is protected by a phthalyl group and in which the a -amino group of the N-terminal amino acid is protected by a tertiary-butyloxy carbonyl group, or an ester, amide, hydrazide or salt thereof and the preparation of a peptide containing a radical of an a ,o -diamino alkanoic acid containing 4 to 6 carbon atoms, which comprises condensing an a ,o -diamino-alkanoic acid having 4 to 6 carbon atoms or a peptide containing such an amino acid with another amino acid or peptide, the a -amino group not taking part in the condensation reaction being protected during the condensation by a tertiary-butyloxy carbonyl group and the o -amino group being protected during the condensation by a phthalyl group, and after the condensation the tertiary-butyloxy carbonyl group is removed by an acidic agent and the phthalyl group is split off in the presence of hydrazine in a weakly acidic medium. Na -Tertiary butyloxycarbonyl - No - phthalyl-diamino alkanoic acids are prepared by removing the carbobenzoxyl group from an Na -tertiary - butyloxycarbonyl - No - carbobenzoxy-diamino alkanoic acid by catalytic hydrogenation and reacting the product with N-carbethoxyphthalimide. Examples are given of the preparation of the partial-sequence of the amino acids 15-24 of corticotropine (i.e. BOC-Lys (Pht) - Lys (Pht) - Arg(NO2) - Arg(NO2) - Pro- Val - Lys(Pht) - Val - Tyr - Pro - OPAB, where BOC is the tertiary-butoxy carbonyl group, Pht, the phthalyl group and PAB the paraphenylazobenzyl group) by stepwise synthesis from proline-para phenyl azo benzyl ester and a - MSH (Ac - Ser - Tyr - Ser - Met - Glu - His - Phe - Arg - Try - Gly - Lys - Pro - Val - NH2) from Lys11-N-phthyl-a -MSH in turn prepared from the tripeptide Lys(Pht)-Pro-Val NH2 and the decapeptide BOC - Ser - Tyr - Ser - Met-Glu (OC4H9 tert) - His - Phe - Arg - Try - Glu-OH.
GB3457362A 1961-09-13 1962-09-10 Peptides and process for their manufacture Expired GB1014426A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1059961A CH437337A (en) 1961-09-13 1961-09-13 Process for the production of peptides
CH306962 1962-03-14

Publications (1)

Publication Number Publication Date
GB1014426A true GB1014426A (en) 1965-12-22

Family

ID=25692097

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3457362A Expired GB1014426A (en) 1961-09-13 1962-09-10 Peptides and process for their manufacture

Country Status (1)

Country Link
GB (1) GB1014426A (en)

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