Chemoselective rapid azo-coupling reaction for bioconjugation
AssigneeThe Trustees of Boston College
InventorsAbhishek Chatterjee, Partha Sarathi Addy
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Abstract
Novel biomolecular conjugates containing non-natural aromatic chemical moieties covalently coupled to a diazonium compound and methods of their use are disclosed.
Claims19
A chemoselectively modified biomolecular conjugate comprising a protein, polypeptide or a peptide comprising naturally-occurring amino acids and one, or more, non-naturally-occurring amino acids comprising a surface-exposed 5-hydroxytryptophan or a 5-aminotryptophan moiety incorporated into the protein, polypeptide or peptide, wherein the non-naturally-occurring amino acid comprising the 5-hydroxytryptophan or the 5-aminotryptophan is chemoselectively modified over the naturally-occurring amino acids of the biomolecule, wherein the 5-hydroxytryptophan or the 5-aminotroptophan is covalently coupled to an aryl-diazonium compound selected from the group consisting of:
- 4-nitorbenzenediazonium (4NDz);
- 4-carboxybenzenediazonium (4NCDz) or 4-methoxvhenzenediazonium (4MCDz).
A chemoselectively labeled antibody conjugate, or antibody fragment conjugate, wherein the antibody, or antibody fragment comprises naturally-occurring amino acids and one, or more, non-naturally-occurring amino acids comprising a surface-exposed 5-hydroxytryptophan or a 5-aminotryptophan moiety incorporated into the antibody, wherein the non-naturally-occurring amino acid comprising 5-hydroxytryptophan or the 5-aminotryptophan is chemoselectively modified over the naturally-occurring amino acids of the biomolecule, wherein 5-hydroxytryptophan or the 5-aminotryptophan is covalently coupled to a detectably-labeled aryl-diazonium compound selected from the group consisting of:
- 4-nitrobenzenediazonium (4NDz);
- 4-carboxybenzenediazonium (4NCDz) or 4-methoxybenzenediazonium (4MCDz).
Dependencies are inferred from the claim text.