Synthetic glycosulfopeptides and methods of synthesis thereof
OwnerRichard D. Cummings, Rodger P. McEverinventors
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Abstract
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 β1,6 linkage to a GalNAc. 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.
Claims32
A compound comprising the formula:
- 2
- wherein:
- R is one of R1, R3-R13 or R15 of FIGS. 6A-6C;
- Tyr is a tyrosine residue;
- SO3− is a sulfate group;
- C is an O-, N-, or S-linking amino acid residue;
- and
- A, B and D are chains of from 0 to 12 amino acids each, with the proviso that the compound comprises no more than 38 amino acid residues.
Dependencies are inferred from the claim text.