WO2001005757A3 - Process for the deprotection of protected thiols - Google Patents

Process for the deprotection of protected thiols Download PDF

Info

Publication number
WO2001005757A3
WO2001005757A3 PCT/GB2000/002796 GB0002796W WO0105757A3 WO 2001005757 A3 WO2001005757 A3 WO 2001005757A3 GB 0002796 W GB0002796 W GB 0002796W WO 0105757 A3 WO0105757 A3 WO 0105757A3
Authority
WO
WIPO (PCT)
Prior art keywords
deprotection
peptides
protected thiol
disulphide
disulphide bridges
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/GB2000/002796
Other languages
French (fr)
Other versions
WO2001005757A2 (en
Inventor
Alan Cuthbertson
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.)
GE Healthcare AS
Original Assignee
Nycomed Imaging AS
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 GBGB9916919.5A external-priority patent/GB9916919D0/en
Priority claimed from GB0003926A external-priority patent/GB0003926D0/en
Priority claimed from GB0007865A external-priority patent/GB0007865D0/en
Priority to EP00946168A priority Critical patent/EP1196429B1/en
Priority to JP2001511418A priority patent/JP4738683B2/en
Application filed by Nycomed Imaging AS filed Critical Nycomed Imaging AS
Priority to DE60026708T priority patent/DE60026708T2/en
Priority to AU60041/00A priority patent/AU6004100A/en
Publication of WO2001005757A2 publication Critical patent/WO2001005757A2/en
Publication of WO2001005757A3 publication Critical patent/WO2001005757A3/en
Priority to US10/052,300 priority patent/US6906171B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • 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
    • C07K14/43504—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from invertebrates
    • 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
    • C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
    • 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
    • C07K7/16—Oxytocins; Vasopressins; Related peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Analytical Chemistry (AREA)
  • Toxicology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Crystals, And After-Treatments Of Crystals (AREA)
  • Cephalosporin Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

The synthesis of peptides comprising disulphide bridges is challenging since it is difficult to ensure that the correct cysteine residues combine to form the desired disulphide bridges. The present invention describes novel protection techniques useful in the preparation of peptides. Described is a process for the deprotection of an Acm-, MBzl- and/or tBu-protected thiol which comprises reacting said protected thiol with an acid in the presence of an oxidising agent at a temperature sufficient to effect deprotection and generation of disulphide bonds.
PCT/GB2000/002796 1999-07-19 2000-07-19 Process for the deprotection of protected thiols Ceased WO2001005757A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU60041/00A AU6004100A (en) 1999-07-19 2000-07-19 Process for the deprotection of protected thiols
DE60026708T DE60026708T2 (en) 1999-07-19 2000-07-19 METHOD FOR THE PROTECTION OF PROTECTED THIOLS
EP00946168A EP1196429B1 (en) 1999-07-19 2000-07-19 Process for the deprotection of protected thiols
JP2001511418A JP4738683B2 (en) 1999-07-19 2000-07-19 Method for deprotecting a protected thiol
US10/052,300 US6906171B2 (en) 1999-07-19 2002-01-18 Process for the deprotection of protected thiols

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
GBGB9916919.5A GB9916919D0 (en) 1999-07-19 1999-07-19 Process for the deprotection of protected thiols
GB9916919.5 1999-07-19
US14686699P 1999-08-03 1999-08-03
GB0003926A GB0003926D0 (en) 2000-02-18 2000-02-18 Process for the deprotection of protected thiols
GB0003926.3 2000-02-18
GB0007865A GB0007865D0 (en) 2000-03-31 2000-03-31 Process for the deprotection of protected thiols
GB0007865.9 2000-03-31

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/052,300 Continuation US6906171B2 (en) 1999-07-19 2002-01-18 Process for the deprotection of protected thiols

Publications (2)

Publication Number Publication Date
WO2001005757A2 WO2001005757A2 (en) 2001-01-25
WO2001005757A3 true WO2001005757A3 (en) 2001-07-19

Family

ID=27255545

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2000/002796 Ceased WO2001005757A2 (en) 1999-07-19 2000-07-19 Process for the deprotection of protected thiols

Country Status (8)

Country Link
US (1) US6906171B2 (en)
EP (1) EP1196429B1 (en)
JP (1) JP4738683B2 (en)
AT (1) ATE320442T1 (en)
AU (1) AU6004100A (en)
DE (1) DE60026708T2 (en)
ES (1) ES2267551T3 (en)
WO (1) WO2001005757A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7772188B2 (en) * 2003-01-28 2010-08-10 Ironwood Pharmaceuticals, Inc. Methods and compositions for the treatment of gastrointestinal disorders
DE04759123T1 (en) * 2003-04-07 2005-08-18 Novetide Ltd. PROCESS FOR PREPARING CYCLIC PEPTIDES
CN102532264A (en) * 2004-06-16 2012-07-04 通用电气医疗集团股份有限公司 Peptide-based compounds
EP1781339B1 (en) * 2004-06-25 2013-12-25 Thomas Jefferson University Guanylyl cyclase C ligands
EP1921087A1 (en) * 2006-11-10 2008-05-14 Primm S.R.L. Process for the preparation of cyclic peptides
US20110306561A1 (en) * 2009-02-12 2011-12-15 Yeda Research And Devlopment Co. Ltd. COMPLEMENT C3a DERIVED DIMERIC PEPTIDES AND USES THEREOF
GB0918321D0 (en) 2009-10-20 2009-12-02 Ge Healthcare As Cyclic peptide synthesis
CA2877868C (en) 2012-06-15 2020-04-21 Husky Injection Molding Systems Ltd. A multi-property injection molding nozzle
US10858389B2 (en) 2015-03-26 2020-12-08 Amgen Inc. Solution phase method for preparing etelcalcetide

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
B HARGITTAI & G BARANY: "Controlled synthesis of natural and disulfide-mispaired regioisomers of alpha-conotoxin SI", JOURNAL OF PEPTIDE RESEARCH., vol. 54, no. 6, June 1999 (1999-06-01), MUNKSGAARD INTERNATIONAL PUBLISHERS, COPENHAGEN., DK, pages 468 - 479, XP002157223, ISSN: 1397-002X *
M ENGEBRETSEN ET AL.: "UNEXPECTED LABILITY OF CYSTEINE ACETAMIDOMETHYL THIOL PROTECTING GROUP", JOURNAL OF PEPTIDE RESEARCH., vol. 49, no. 4, April 1997 (1997-04-01), MUNKSGAARD INTERNATIONAL PUBLISHERS, COPENHAGEN., DK, pages 341 - 346, XP000687316, ISSN: 1397-002X *
T KOIDE ET AL.: "Investigation of the dimethylsulfoxide-trifluoroacetic acid oxidation system for the synthesis of cystine-containing peptides", CHEMICAL AND PHARMACEUTICAL BULLETIN., vol. 41, no. 6, 1993, PHARMACEUTICAL SOCIETY OF JAPAN. TOKYO., JP, pages 1030 - 1034, XP002157224, ISSN: 0009-2363 *

Also Published As

Publication number Publication date
AU6004100A (en) 2001-02-05
EP1196429A2 (en) 2002-04-17
ES2267551T3 (en) 2007-03-16
DE60026708D1 (en) 2006-05-11
US20020143207A1 (en) 2002-10-03
DE60026708T2 (en) 2006-12-14
US6906171B2 (en) 2005-06-14
WO2001005757A2 (en) 2001-01-25
JP4738683B2 (en) 2011-08-03
ATE320442T1 (en) 2006-04-15
EP1196429B1 (en) 2006-03-15
JP2003505368A (en) 2003-02-12

Similar Documents

Publication Publication Date Title
WO2001005757A3 (en) Process for the deprotection of protected thiols
ES2517817T3 (en) Keratin fiber straightening process with a heating medium and a denaturing agent
GB0703060D0 (en) Peptide
IL144259A0 (en) Methods for making proteins containing free cysteine residues
WO2000010512A3 (en) Enhanced antiperspirant salts stabilized with calcium and concentrated aqueous solutions of such salts
WO2000075399A3 (en) Composition and method for inhibition of metal corrosion
AP2000001888A0 (en) Method for treatment of diabetes using peptides analogues of insulin.
BR9809306A (en) Protease inhibitors
WO2000073452A3 (en) Compositions and methods for the treatment of immune related diseases
EP2962699A3 (en) Improved method for preparing conjugates of proteins and chelating agents
PL367957A1 (en) Use of a copolymer to produce a galenic form containing a peptide or a protein as active agent
WO2003020963A3 (en) Proteins in type 2 diabetes
EP0816490A3 (en) Mutant prenyl diphosphate synthase
JPS6027680B2 (en) Method for producing keratin hydrolyzate
BR0315055A (en) Pyrimidin-4,6-dicarboxylic acid diacids for selective collagenase inhibition
WO2002056840A3 (en) Cosmetic and/or pharmaceutical agent containing acylated amino acid
CN100352419C (en) Use of dimercaptoamides for permanently deforming of keratinic fibres
WO2001072327A3 (en) Use of analogues of superoxide dismutase for treating hepatocellular insufficiencies
WO2002079251A3 (en) Method for making human insulin precursors
AU2002327514A1 (en) Application of peptide conjugates to alzheimer's disease
WO2001034639A3 (en) β-AMINOACID COMPOUNDS USEFUL FOR INHIBITING β-AMYLOID PEPTIDE RELEASE AND/OR ITS SYNTHESIS
WO2006136906A3 (en) Switch-peptides as tool for the study of fibrillogenesis
US20060013784A1 (en) Novel dimercaptoamides, compositions comprising them as reducing agents, and processes for permanently reshaping keratin fibers therewith
WO2003025014A3 (en) Use of peptides comprising post-translational modifications in the treatment of autoimmune pathologies
WO2001009292A3 (en) Sentrin-specific human proteases senp1-3

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AT AU AZ BA BB BG BR BY BZ CA CH CN CR CU CZ CZ DE DE DK DK DM DZ EE EE ES FI FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): AE AG AL AM AT AT AU AZ BA BB BG BR BY BZ CA CH CN CR CU CZ CZ DE DE DK DK DM DZ EE EE ES FI FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

WWE Wipo information: entry into national phase

Ref document number: 2000946168

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 10052300

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 2000946168

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWG Wipo information: grant in national office

Ref document number: 2000946168

Country of ref document: EP