title: Site-Specific Dual Functionalization of Cysteine Residue in Peptides and Proteins with 2-Azidoacrylates.
abstract: Herein, we report use of 2-azidoacrylates to perform site-specific dual functionalization of the cysteine residue of peptides and bovine serum albumin (BSA), a native protein containing one free cysteine residue. The sulfhydryl group of the cysteine residue could be conjugated with 2-azidoacrylates bearing various functionalities, such as fluorescent dyes under physiological aqueous buffer conditions, to afford peptide and protein conjugates anchoring an azide moiety. Successive azide-alkyne cycloaddition enables installation of the second functionality, thus affording dual-functionalized peptide- and protein-based materials.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , 637371 Singapore.
authors.forename: Shinya
authors.initials: S
authors.lastname: Ariyasu
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , 637371 Singapore.
authors.forename: Hirohito
authors.initials: H
authors.lastname: Hayashi
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , 637371 Singapore.
authors.forename: Bengang
authors.identifier: 0000-0002-8391-1234
authors.initials: B
authors.lastname: Xing
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , 637371 Singapore.
authors.forename: Shunsuke
authors.identifier: 0000-0003-2039-023X
authors.initials: S
authors.lastname: Chiba
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry; D000818:Animals; D001386:Azides / Q000737:chemistry*; D002417:Cattle; D057930:Click Chemistry; D003545:Cysteine / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry; D008958:Models, Molecular; D010455:Peptides / Q000737:chemistry*; D012710:Serum Albumin, Bovine / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D000179:Acrylates; D000480:Alkynes; D001386:Azides; D005456:Fluorescent Dyes; D010455:Peptides; D013438:Sulfhydryl Compounds; D012710:Serum Albumin, Bovine; D003545:Cysteine