title: Derivatization of phosphopeptides with mercapto- and amino-functionalized conjugate groups by phosphate elimination and subsequent Michael addition.
abstract: Kinetics of the beta-elimination of the phosphate group from H-Tyr-Ser(PO3H2)-Phe-OH and H-Tyr-Thr(PO3H2)-Phe-OH and subsequent addition of thiols and amines to the dehydroalaninyl and beta-methyldehydroalaninyl residues formed, were followed by RP HPLC under alkaline conditions in the absence and presence of Ba2+ ions. By this reaction sequence, the phosphoserinyl peptide was conjugated with mono-N-(2-mercaptoethyl)amide of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (4), a mercapto-functionalized pentapeptide, H-His-Gly-Gly-His-Gly-NH(CH2)4SH, and an amino-functionalized fluorescent dye, 5-dimethylaminonaphthalene-1-[N-(5-aminopentyl)]sulfonamide (dansyl cadaverine). The beta-methyldehydroalanine residue was, in turn, observed to be a poor Michael acceptor.
authors.affiliation: Department of Chemistry, University of Turku, FIN-20014, Turku, Finland.
authors.forename: Kati
authors.initials: K
authors.lastname: Mattila
authors.forename: Jaana
authors.initials: J
authors.lastname: Siltainsuu
authors.forename: Lajos
authors.initials: L
authors.lastname: Balaspiri
authors.forename: Mikko
authors.initials: M
authors.lastname: Ora
authors.forename: Harri
authors.initials: H
authors.lastname: Lönnberg
mesh_terms: D000588:Amines / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry; D010748:Phosphopeptides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D000588:Amines; D010710:Phosphates; D010748:Phosphopeptides; D013438:Sulfhydryl Compounds