WO2004101597A3 - Methods for the reduction of disulfide bonds - Google Patents

Methods for the reduction of disulfide bonds Download PDF

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Publication number
WO2004101597A3
WO2004101597A3 PCT/IL2004/000392 IL2004000392W WO2004101597A3 WO 2004101597 A3 WO2004101597 A3 WO 2004101597A3 IL 2004000392 W IL2004000392 W IL 2004000392W WO 2004101597 A3 WO2004101597 A3 WO 2004101597A3
Authority
WO
WIPO (PCT)
Prior art keywords
unsubstituted
branched
cyclic
substituted linear
dihydroxybutane
Prior art date
Application number
PCT/IL2004/000392
Other languages
French (fr)
Other versions
WO2004101597A2 (en
Inventor
Michael Mizhiritskii
Yacov Shpernat
Boris Ashkenazi
Original Assignee
Frutarom Ltd
Michael Mizhiritskii
Yacov Shpernat
Boris Ashkenazi
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 Frutarom Ltd, Michael Mizhiritskii, Yacov Shpernat, Boris Ashkenazi filed Critical Frutarom Ltd
Publication of WO2004101597A2 publication Critical patent/WO2004101597A2/en
Publication of WO2004101597A3 publication Critical patent/WO2004101597A3/en

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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
    • C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
    • C07K1/113—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure
    • C07K1/1133—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure by redox-reactions involving cystein/cystin side chains

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Analytical Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Peptides Or Proteins (AREA)

Abstract

This invention provides a method for reducing disulfide bonds in a chemical agent, the method may include, inter alia, the step of contacting the chemical agent with 1,4-dimercapto-2,3-dihydroxybutane, wherein the 1,4-dimercapto-2,3­dihydroxybutane is prepared by a non-stereoselective reaction. This invention further provides a method for protecting a protein against oxidation, the method may include, inter alia, the step of contacting the protein with 1,4-dimercapto-2,3­dihydroxybutane, wherein the 1,4-dimercapto-2,3-dihydroxybutane is prepared by a non-stereoselective reaction. This invention further provides a method for reducing a disulfide bond in a. chemical agent, the method may include, inter alia, the step of contacting the chemical agent with a compound represented by the structure of formula (I) wherein R1, R2 and R3 are the same or different, independently of each other represent H, an unsubstituted or substituted linear, branched or cyclic hydroxyalkyl, an unsubstituted or substituted linear, branched or cyclic hydroxyalkenyl or an unsubstituted or substituted hydroxyaryl, an unsubstituted or substituted linear, branched or cyclic alkoxyalkyl ether, an unsubstituted or substituted linear, branched or cyclic alkoxy alkoxyalkyl ether, an unsubstituted or substituted linear, branched or cyclic alkylthioalkyl ether. This invention further provides a method for protecting a protein against oxidation, the method may include, inter alia, the step of contacting the protein with a compound represented by the structure of formula (I) wherein R1, R2 and R3 are the same or different, independently of each other represent H, an unsubstituted or substituted linear, branched or cyclic hydroxyalkenyl, an unsubstituted or substituted linear, branched or cyclic hydroxyalkenyl or an unsubstituted hydroxyaryl, an unsubstituted or subsituted linear, branched or cyclic alkoxyalkyl ether, an unsubstituted or substituted linear, branched or cyclic alkoxy alkoxyalkyl ether, an unsubstituted or substituted linear, branched or cyclic alkylthioalkyl ether.
PCT/IL2004/000392 2003-05-13 2004-05-10 Methods for the reduction of disulfide bonds WO2004101597A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US46982103P 2003-05-13 2003-05-13
US60/469,821 2003-05-13

Publications (2)

Publication Number Publication Date
WO2004101597A2 WO2004101597A2 (en) 2004-11-25
WO2004101597A3 true WO2004101597A3 (en) 2005-09-09

Family

ID=33452325

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IL2004/000392 WO2004101597A2 (en) 2003-05-13 2004-05-10 Methods for the reduction of disulfide bonds

Country Status (1)

Country Link
WO (1) WO2004101597A2 (en)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7173003B2 (en) 2001-10-10 2007-02-06 Neose Technologies, Inc. Granulocyte colony stimulating factor: remodeling and glycoconjugation of G-CSF
US7214660B2 (en) 2001-10-10 2007-05-08 Neose Technologies, Inc. Erythropoietin: remodeling and glycoconjugation of erythropoietin
MXPA05010773A (en) 2003-04-09 2005-12-12 Neose Technologies Inc Glycopegylation methods and proteins/peptides produced by the methods.
WO2005012484A2 (en) 2003-07-25 2005-02-10 Neose Technologies, Inc. Antibody-toxin conjugates
US20080305992A1 (en) 2003-11-24 2008-12-11 Neose Technologies, Inc. Glycopegylated erythropoietin
US20080300173A1 (en) 2004-07-13 2008-12-04 Defrees Shawn Branched Peg Remodeling and Glycosylation of Glucagon-Like Peptides-1 [Glp-1]
JP5948627B2 (en) 2004-10-29 2016-07-20 レイショファーム ゲーエムベーハー Fibroblast growth factor (FGF) remodeling and carbohydrate pegylation
EP1858543B1 (en) 2005-01-10 2013-11-27 BioGeneriX AG Glycopegylated granulocyte colony stimulating factor
US20070154992A1 (en) 2005-04-08 2007-07-05 Neose Technologies, Inc. Compositions and methods for the preparation of protease resistant human growth hormone glycosylation mutants
EP1893632B1 (en) 2005-06-17 2015-08-12 Novo Nordisk Health Care AG Selective reduction and derivatization of engineered factor vii proteins comprising at least one non-native cysteine
US20070105755A1 (en) 2005-10-26 2007-05-10 Neose Technologies, Inc. One pot desialylation and glycopegylation of therapeutic peptides
US20090048440A1 (en) 2005-11-03 2009-02-19 Neose Technologies, Inc. Nucleotide Sugar Purification Using Membranes
CN101516388B (en) 2006-07-21 2012-10-31 诺和诺德公司 Glycosylation of peptides via O-linked glycosylation sequences
EP2054521A4 (en) 2006-10-03 2012-12-19 Novo Nordisk As Methods for the purification of polypeptide conjugates
RS52845B (en) 2007-04-03 2013-12-31 Biogenerix Ag Methods of treatment using glycopegylated g-csf
US9493499B2 (en) 2007-06-12 2016-11-15 Novo Nordisk A/S Process for the production of purified cytidinemonophosphate-sialic acid-polyalkylene oxide (CMP-SA-PEG) as modified nucleotide sugars via anion exchange chromatography
EP2257311B1 (en) 2008-02-27 2014-04-16 Novo Nordisk A/S Conjugated factor viii molecules
US11219690B2 (en) 2013-12-13 2022-01-11 Novo Nordisk Healthcare Ag Method for thioether conjugation of proteins

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NETHERTON M.R. ET AL: "Air-Stable Trialkylphosphonium Salts: Simple, Practical, and Versatile Replacements for Air-Sensitive Trialkylphosphines. Applications in Stoichiometric and Catalytic Processes", ORGANIC LETTERS, vol. 3, no. 26, December 2001 (2001-12-01), pages 4295 - 4298, XP002989079 *

Also Published As

Publication number Publication date
WO2004101597A2 (en) 2004-11-25

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