GB1210557A - Synthesis of polypeptides containing cysteine - Google Patents

Synthesis of polypeptides containing cysteine

Info

Publication number
GB1210557A
GB1210557A GB1546968A GB1546968A GB1210557A GB 1210557 A GB1210557 A GB 1210557A GB 1546968 A GB1546968 A GB 1546968A GB 1546968 A GB1546968 A GB 1546968A GB 1210557 A GB1210557 A GB 1210557A
Authority
GB
United Kingdom
Prior art keywords
cys
gly
leu
val
ome
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
GB1546968A
Inventor
Helmut Zahn
Gunther Schmidt
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of GB1210557A publication Critical patent/GB1210557A/en
Expired legal-status Critical Current

Links

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
    • C07K1/067—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
    • 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
    • C07K14/62—Insulins
    • 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
    • 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)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Analytical Chemistry (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

1,210,557. Disulphide peptides. FARBENFABRIKEN BAYER A.G. 1 April, 1968 [1 April, 1967; 5 Jan., 1968], No. 15469/68. Heading C2C. Single chain polypeptides with at least one cysteine residue are prepared by (1) synthesis of a first symmetrical cystinyl peptide consisting of 2 identical amino acid sequences corresponding to one portion of the desired single chain peptide linked by at least one -S-S- bond by incorporating a cystine residue at at least one point where the cysteine residue occurs in the desired peptide; (2) preparing a di- or polymeric intermediate consisting of two or more of the desired polypeptide chains linked by at least one cistinyl -S-S- bond by (a) coupling a second symmetrical cystinyl peptide consisting of 2 amino acid sequences corresponding to the remaining portion of the desired single chain polypeptide with the first symmetrical peptide to give a polymeric intermediate consisting of a number of the desired polypeptide chains linked by cystinyl -S-S- bands; or (b) coupling a single chain consisting of an amino acid sequence corresponding to the remaining portion of the desired single chain polypeptide with the first symmetrical peptide to give a dimeric intermediate consisting of 2 of the desired polypeptide chains linked by at least one cystinyl -S-S- bond; and (3) splitting the -S-S- bonds of the intermediate. The synthesis of insulin by the above method is described and intermediates isolated are (Z - Cys - Gly - OMe) 2 ; (Z - Leu - Cys - Gly- OMe) 2 ; (Z - His - Leu - Cys - Gly - OMe) 2 ; (Z - Gln - His - Leu - Cys - Gly - OMe) 2 ; (ZAsn - Gln - His - Leu - Cys- Gly - OMe)2; (Z - Val - Asn - Gln - His - Leu - Cys - Gly- OMe) 4 ; (Z - Phe - Val - Asn - Gln - His - Leu- Cys - Gly OMe) 2 ; (Z - Phe - Val - Asn - Gln- His - Leu - Cys - Gly - N 2 H 3 ) 2 ; Z - Ser(But)- His - Leu - Val - Glu(OBut) - N 2 H 3 ; Z - Ser (But) - His - Leu - Val - Glu(OBut) - Ala - Leu- Tyr(But) - OMe; (Z - Val - Cys - Gly - OMe) 2 ; (Z - Leu - Val - Cys - Gly - OMe) 2 ; (Tri - Leu- Val - Cys - Gly - OMe) 2 ; (Tri - Leu - Val - Cys- Gly - OH) 2 ; (Tri - Leu - Val - Cys - Gly- N 2 H 3 ) 2 ; (Tri - Leu - Val - Cys - Gly - Glu (OBut) - Arg - Gly - OH) 2 ; (Tri - Leu - Val- Cys - Gly - Glu(OBut) - Arg - Gly - Phe - Phe- Tyr(But) - Thr(But) - Pro - Lys(BOC) - Ala- OBut) 2 ; (Z - Phe - Val - Asn - Gln - His Leu- Cys - Gly - Ser(But) - His - Leu - Val - Glu (OBut) - Ala - Leu - Tyr(But) - OMe) 2 ; (Z - Cys- Ala - Gly - OMe) 2 ; (BOC - Cys(TR1) - Cys- Ala - Gly - OMe) 2 ; (BOC - Gln - Cys(TR1) - Cys- Ala - Gly - OMe) 2 ; (BOC - Gly - Ile - Val- Glu(OBut) - Gln - Cys(TRl) - Cys - Ala - Gly- OMe) 2 ; (BOC - Gly - Ile - Val - Glu(OBut). Gin - Cys(TRl) - Cys - Ala - Gly - N 2 H 3 ) 2 (BOC - Cys - ONp) 2 ; (BOC - Cys - Asn - OBz) 2 ; (BOC - Tyr(Bz) - Cys - Asn - OBz) 2 ; (BOCAsn - Tyr(Bz) - Cys - Asn - OBz) 2 ; (BOCGlu(OBz) - Asn - Tyr(Bz) - Cys - Asn - OBz) 2 ; (Trl - Leu - Tyr(But) - Gln - Leu - Glu(OBz)- Asn - Tyr(Bz) - Cys - Asn - OBz) 2 ; and (TR1- Val - Cys(TR1) - Ser- Leu - Tyr - Gln - Leu- Glu(OBz) - Asn - Tyr(Bz) - Cys - Asn - OBz) 2 .
GB1546968A 1967-04-01 1968-04-01 Synthesis of polypeptides containing cysteine Expired GB1210557A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0052000 1967-04-01

Publications (1)

Publication Number Publication Date
GB1210557A true GB1210557A (en) 1970-10-28

Family

ID=7105092

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1546968A Expired GB1210557A (en) 1967-04-01 1968-04-01 Synthesis of polypeptides containing cysteine

Country Status (6)

Country Link
BE (1) BE713055A (en)
CH (1) CH507207A (en)
DE (1) DE1593866A1 (en)
FR (1) FR1573151A (en)
GB (1) GB1210557A (en)
NL (1) NL6803646A (en)

Also Published As

Publication number Publication date
BE713055A (en) 1968-10-01
FR1573151A (en) 1969-07-04
DE1593866A1 (en) 1971-02-25
NL6803646A (en) 1968-10-02
CH507207A (en) 1971-05-15

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Legal Events

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