title: Traceless and Chemoselective Amine Bioconjugation via Phthalimidine Formation in Native Protein Modification.
abstract: ortho-Phthalaldehyde (OPA) and its derivatives are found to react chemoselectively with amino groups on peptides and proteins rapidly and tracelessly under the physiological condition via formation of phthalimidines, which provides a novel and promising approach when performing bioconjugation on native proteins. The notable advantages of this method over the existing native protein lysine-labeling approaches include a traceless process, a self-reacting, specific and fast reaction, ease of operation, and the ability to use nonhydrolyzable reagents. Its applications have been effectively demonstrated including conjugation of peptides and proteins, and generation of an active PEGlyated l-asparaginase.
authors.affiliation: Department of Chemistry, The State Key Laboratory of Synthetic Chemistry, The University of Hong Kong , Hong Kong, China.
authors.forename: Chun Ling
authors.initials: CL
authors.lastname: Tung
authors.affiliation: Department of Chemistry, The State Key Laboratory of Synthetic Chemistry, The University of Hong Kong , Hong Kong, China.
authors.forename: Clarence T T
authors.initials: CT
authors.lastname: Wong
authors.affiliation: Department of Chemistry, The State Key Laboratory of Synthetic Chemistry, The University of Hong Kong , Hong Kong, China.
authors.forename: Eva Yi Man
authors.initials: EY
authors.lastname: Fung
authors.affiliation: Department of Chemistry, The State Key Laboratory of Synthetic Chemistry, The University of Hong Kong , Hong Kong, China.
authors.forename: Xuechen
authors.initials: X
authors.lastname: Li
mesh_terms: D001215:Asparaginase / Q000737:chemistry; D055767:Immobilized Proteins / Q000737:chemistry*; D008164:Luminescent Proteins / Q000737:chemistry; D015394:Molecular Structure; D010797:Phthalimides / Q000737:chemistry*; D011092:Polyethylene Glycols / Q000737:chemistry; D000097573:Red Fluorescent Protein
chemical_list: D001215:Asparaginase; D055767:Immobilized Proteins; D008164:Luminescent Proteins; D010797:Phthalimides; D011092:Polyethylene Glycols; D000097573:Red Fluorescent Protein; C037432:phthalimidine