US 11,890,351 B2
Chemoselective rapid azo-coupling reaction for bioconjugation
Abhishek Chatterjee, Brookline, MA (US); and Partha Sarathi Addy, Brighton, MA (US)
Assigned to Trustees of Boston College, Chestnut Hill, MA (US)
Filed by Trustees of Boston College, Chestnut Hill, MA (US)
Filed on Jun. 19, 2018, as Appl. No. 16/012,060.
Claims priority of provisional application 62/522,282, filed on Jun. 20, 2017.
Prior Publication US 2018/0360984 A1, Dec. 20, 2018
Int. Cl. A61K 47/68 (2017.01); C07K 16/32 (2006.01); A61K 47/54 (2017.01); A61K 49/00 (2006.01); C07D 209/20 (2006.01); C07H 21/00 (2006.01); A61K 51/10 (2006.01)
CPC A61K 47/6851 (2017.08) [A61K 47/549 (2017.08); A61K 47/6803 (2017.08); A61K 49/0043 (2013.01); A61K 49/0058 (2013.01); A61K 51/1045 (2013.01); C07D 209/20 (2013.01); C07H 21/00 (2013.01); C07K 16/32 (2013.01); C07K 2317/24 (2013.01); C07K 2317/55 (2013.01)] 19 Claims
 
1. 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).