title: Tyrosine-Specific Chemical Modification with in Situ Hemin-Activated Luminol Derivatives.
abstract: Tyrosine-specific chemical modification was achieved using in situ hemin-activated luminol derivatives. Tyrosine residues in peptide and protein were modified effectively with N-methylated luminol derivatives under oxidative conditions in the presence of hemin and H2O2. Both single and double modifications of the tyrosine residue occurred in the reaction of angiotensin II with N-methylated luminol derivative 9. Tyrosine-specific chemical modification of the model protein bovine serum albumin (BSA) revealed that the surface-exposed tyrosine residues were selectively modified with 9. We succeeded in the functionalization of several proteins using azide-conjugated compound 18 using alkyne-conjugated probes by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) or dibenzocyclooctyne (DBCO)-mediated copper-free click chemistry. This tyrosine-specific modification was orthogonal to conventional lysine modification by N-hydroxysuccinimide (NHS) ester, and dual functionalization by fluorescence modification of tyrosine residues and PEG modification of lysine residues was achieved without affecting the modification efficiency.
authors.affiliation: Chemical Resources Laboratory, Tokyo Institute of Technology , Yokohama 226-8503, Japan.
authors.forename: Shinichi
authors.initials: S
authors.lastname: Sato
authors.affiliation: Chemical Resources Laboratory, Tokyo Institute of Technology , Yokohama 226-8503, Japan.
authors.forename: Kosuke
authors.initials: K
authors.lastname: Nakamura
authors.affiliation: Chemical Resources Laboratory, Tokyo Institute of Technology , Yokohama 226-8503, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Nakamura
mesh_terms: D000809:Angiotensins / Q000737:chemistry / Q000235:genetics; D000818:Animals; D002417:Cattle; D005455:Fluorescent Antibody Technique; D006427:Hemin / Q000737:chemistry*; D008165:Luminol / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D012710:Serum Albumin, Bovine / Q000737:chemistry; D013329:Structure-Activity Relationship; D014443:Tyrosine / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D000809:Angiotensins; D012710:Serum Albumin, Bovine; D014443:Tyrosine; D008165:Luminol; D006427:Hemin