Remodeling and glycoconjugation of peptides
AssigneeNeose Technologies, Inc.
InventorsShawn DeFrees, David A. Zopf, Caryn Bowe
Life of this patent
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Abstract
The invention includes methods and compositions for remodeling a peptide molecule, including the addition or deletion of one or more glycosyl groups to a peptide, and/or the addition of a modifying group a peptide.
Claims30
A covalent conjugate between a peptide and poly(ethylene glycol), wherein said poly(ethylene glycol) is covalently attached to said peptide at a glycosyl or amino acid residue of said peptide via an intact glycosyl linking group comprising a sialic acid residue covalently linked to said poly(ethylene glycol), wherein said sialic acid residue is covalently attached to said glycosyl or amino acid residue of said peptide by reaction between said peptide and a modified sugar donor comprising sialic acid covalently linked to said poly(ethylene glycol), and wherein said reaction is catalyzed by a sialyltransferase.
A covalent conjugate between a peptide and poly(ethylene glycol), comprising a sialic acid residue having a structure according to the formula:
- in which R is said poly(ethylene glycol) and said poly(ethylene glycol) attached to said sialic acid residue through a linker, and wherein said sialic acid residue is covalently attached to a glycosyl or amino acid residue of said peptide by reaction between said peptide and a modified sugar donor comprising said sialic acid residue covalently linked to said poly(ethylene glycol), and wherein said reaction is catalyzed by a sialyltransferase.
A covalent conjugate between a peptide and poly(ethylene glycol), comprising an intact glycosyl linking group having a structure according to the formula:
- wherein
- R1, R2, R3, R4, and R5 are members independently selected from H, OH, a water-soluble polymer and linker-water-soluble polymer, with the proviso that at least one of R1, R2, R3, R4, and R5 is a member selected from said water-soluble polymer and said linker-water-soluble polymer;
- R6 is a member selected from H, OH and polymers;
- X, Y, Z, A and B are members independently selected from O, NH, S, and CH2;
- and
- wherein said intact glycosyl linking group is covalently attached to a glycosyl or amino acid residue of said peptide by reaction between said peptide and a modified sugar donor comprising said intact glycosyl linking group covalently linked to said poly(ethylene glycol), and wherein said reaction is catalyzed by a glycosyltransferase.
A covalent conjugate of a G-CSF peptide and poly(ethylene glycol) comprising a sialic acid residue conjugated to said poly(ethylene glycol), wherein said residue has a structure according to the formula:
- in which n is an integer from 1 to 2000;
- and
- wherein said sialic acid residue is covalently attached to a glycosyl or amino acid residue of said G-CSF peptide by reaction between said G-CSF peptide and a modified sugar donor comprising said sialic acid residue covalently linked to said poly(ethylene glycol), and wherein said reaction is catalyzed by a sialyltransferase.
Dependencies are inferred from the claim text.