Glycosulfopeptides and methods of synthesis and use thereof

Details Glycosulfopeptides and methods of synthesis and use thereof Glycosulfopeptides and methods of synthesis and use thereof

C - Chemistry, Metallurgy

07

K

C07K 14/705 (2006.01) A61K 38/17 (2006.01) C07H 3/06 (2006.01) C12P 21/02 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2332563

A new class of synthetic glycosulfopeptides (GSPs) which have one or more sulfated tyrosine residues and a glycan linked to the peptide, the glycan preferably including a sialyl Lewisx group or a sialyl Lewisa group. In a preferred version the GSPs have an O-glycan comprising a .beta.1,6 linkage to a Ga1NAc. The present invention further contemplates in vitro methods of the synthesis of these GSPs without the use of the cells and methods of their use in vivo as powerful anti-inflammatory antithrombotic, or anti-metastatic compounds. The invention also contemplates a method of synthesizing oligosaccharides by cleaving the glycan from the GSP.

Cette invention a trait à une nouvelle classe de glycosulfopeptides (GSP) ayant un ou plusieurs restes tyrosine sulfatée et un glycane lié au peptide, ce glycane comportant, de préférence, un groupe sialyl Lewis?x¿ ou un groupe sialyl Lewis?a¿. Dans une version préférée, les GSP possèdent un O-glycane comprenant une liaison .beta.1, 6 avec un N-acétygalactosamine (GalNac). L'invention concerne également des techniques in vitro de synthèse de ces GSP, sans recours aux cellules, ainsi que des techniques permettant de les utiliser in vivo en tant que puissant anti-inflammatoire antithrombotique ou en tant que composés anti-métastatiques. Elle porte, de surcroît, sur une technique de synthèse d'oligosaccharides par clivage du glycane du GSP.

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