Title:
REAGENTS AND METHODS FOR THE FORMATION OF DISULFIDE BONDS AND THE GLYCOSYLATION OF PROTEINS
Document Type and Number:
WIPO Patent Application WO2005000862
Kind Code:
A3
Abstract:
Methods and reagents for the formation of disulfide bonds, particularly in proteins, peptides and amino acids. The methods and reagents are particularly useful for the controlled glycosylation of proteins, peptides and amino acids. The methods utilise thiosulfonate or selenenylsulfide compounds as reagents or intermediates. Some proteins and peptides comprising selenenylsulfide groups also form part of the invention.
Inventors:
DAVIS BENJAMIN GUY (GB)
GAMBLIN DAVID PHILIP (GB)
FAIRBANKS ANTHONY JOHN (GB)
GARNIER PHILIPPE (GB)
GAMBLIN DAVID PHILIP (GB)
FAIRBANKS ANTHONY JOHN (GB)
GARNIER PHILIPPE (GB)
Application Number:
PCT/GB2004/002706
Publication Date:
August 18, 2005
Filing Date:
June 24, 2004
Export Citation:
Assignee:
ISIS INNOVATION (GB)
DAVIS BENJAMIN GUY (GB)
GAMBLIN DAVID PHILIP (GB)
FAIRBANKS ANTHONY JOHN (GB)
GARNIER PHILIPPE (GB)
DAVIS BENJAMIN GUY (GB)
GAMBLIN DAVID PHILIP (GB)
FAIRBANKS ANTHONY JOHN (GB)
GARNIER PHILIPPE (GB)
International Classes:
C07H5/10; C07K1/107; (IPC1-7): C07H5/10; C12N9/56; C12N9/44
Domestic Patent References:
| WO2000001712A2 | 2000-01-13 |
Other References:
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002300619, retrieved from STN Database accession no. AN: 1955:53561
FIELD ET AL.: "Biologically orientated...", J.ORG.CHEM., vol. 36, no. 2, 1971, pages 309 - 313, XP002300617
RAJCA A ET AL: "NEW MIXED DISULFIDES OF L-CYSTEINE DERIVATIVES AND OF GLUTATHIONE WITH DIETHYLDITHIOCARBAMIC ACID AND 2-MERCAPTOETHANESULFONIC ACID", ARZNEIMITTEL FORSCHUNG. DRUG RESEARCH, EDITIO CANTOR. AULENDORF, DE, vol. 40, no. 3, 1990, pages 282 - 286, XP000882932, ISSN: 0004-4172
RAJCA A ET AL: "SYNTHESIS OF UNSYMMETRICAL DISULFIDES WITH THIOLSULFONATES IMMOBILISED ON A POLYSTYRENE SUPPORT", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 31, no. 42, 1990, pages 6075 - 6076, XP000653113, ISSN: 0040-4039
JOHNSTON B D ET AL: "Synthesis of thio-linked disaccharides by 1-->2 intramolecular thioglycosyl migration: oxacarbenium versus episulfonium ion intermediates.", THE JOURNAL OF ORGANIC CHEMISTRY. 28 JUL 2000, vol. 65, no. 15, 28 July 2000 (2000-07-28), pages 4607 - 4617, XP002328859, ISSN: 0022-3263
REICH H J ET AL: "ORGANOSELENIUM CHEMISTRY ALKYLATION OF ACID ESTER AMIDE AND KETONE ENOLATES WITH BROMOMETHYL BENZYL SELENIDE AND SULFIDE PREPARATION OF SELENOCYSTEINE DERIVATIVES", JOURNAL OF ORGANIC CHEMISTRY, vol. 51, no. 15, 1986, pages 2981 - 2988, XP002328860, ISSN: 0022-3263
GAMBLIN DAVID P ET AL: "Glycosyl phenylthiosulfonates (glyco-PTS): novel reagents for glycoprotein synthesis.", ORGANIC & BIOMOLECULAR CHEMISTRY. 7 NOV 2003, vol. 1, no. 21, 7 November 2003 (2003-11-07), pages 3642 - 3644, XP002300618, ISSN: 1477-0520
GAMBLIN DAVID P ET AL: "Glyco-SeS: selenenylsulfide-mediated protein glycoconjugation--a new strategy in post-translational modification.", ANGEWANDTE CHEMIE (INTERNATIONAL ED. IN ENGLISH) 6 FEB 2004, vol. 43, no. 7, 6 February 2004 (2004-02-06), pages 828 - 833, XP002328861, ISSN: 0570-0833
FIELD ET AL.: "Biologically orientated...", J.ORG.CHEM., vol. 36, no. 2, 1971, pages 309 - 313, XP002300617
RAJCA A ET AL: "NEW MIXED DISULFIDES OF L-CYSTEINE DERIVATIVES AND OF GLUTATHIONE WITH DIETHYLDITHIOCARBAMIC ACID AND 2-MERCAPTOETHANESULFONIC ACID", ARZNEIMITTEL FORSCHUNG. DRUG RESEARCH, EDITIO CANTOR. AULENDORF, DE, vol. 40, no. 3, 1990, pages 282 - 286, XP000882932, ISSN: 0004-4172
RAJCA A ET AL: "SYNTHESIS OF UNSYMMETRICAL DISULFIDES WITH THIOLSULFONATES IMMOBILISED ON A POLYSTYRENE SUPPORT", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 31, no. 42, 1990, pages 6075 - 6076, XP000653113, ISSN: 0040-4039
JOHNSTON B D ET AL: "Synthesis of thio-linked disaccharides by 1-->2 intramolecular thioglycosyl migration: oxacarbenium versus episulfonium ion intermediates.", THE JOURNAL OF ORGANIC CHEMISTRY. 28 JUL 2000, vol. 65, no. 15, 28 July 2000 (2000-07-28), pages 4607 - 4617, XP002328859, ISSN: 0022-3263
REICH H J ET AL: "ORGANOSELENIUM CHEMISTRY ALKYLATION OF ACID ESTER AMIDE AND KETONE ENOLATES WITH BROMOMETHYL BENZYL SELENIDE AND SULFIDE PREPARATION OF SELENOCYSTEINE DERIVATIVES", JOURNAL OF ORGANIC CHEMISTRY, vol. 51, no. 15, 1986, pages 2981 - 2988, XP002328860, ISSN: 0022-3263
GAMBLIN DAVID P ET AL: "Glycosyl phenylthiosulfonates (glyco-PTS): novel reagents for glycoprotein synthesis.", ORGANIC & BIOMOLECULAR CHEMISTRY. 7 NOV 2003, vol. 1, no. 21, 7 November 2003 (2003-11-07), pages 3642 - 3644, XP002300618, ISSN: 1477-0520
GAMBLIN DAVID P ET AL: "Glyco-SeS: selenenylsulfide-mediated protein glycoconjugation--a new strategy in post-translational modification.", ANGEWANDTE CHEMIE (INTERNATIONAL ED. IN ENGLISH) 6 FEB 2004, vol. 43, no. 7, 6 February 2004 (2004-02-06), pages 828 - 833, XP002328861, ISSN: 0570-0833
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