Derivatization of phosphopeptides with mercapto- and amino-functionalized conjugate groups by phosphate elimination and subsequent Michael addition



: Mattila K, Siltainsuu J, Balaspiri L, Ora M, Lonnberg H

Publisher: ROYAL SOC CHEMISTRY

: 2005

: Organic and Biomolecular Chemistry

: ORGANIC & BIOMOLECULAR CHEMISTRY

: ORG BIOMOL CHEM

: 3

: 16

: 3039

: 3044

: 6

: 1477-0520

DOI: https://doi.org/10.1039/b505573c


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)(4)SH, 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.



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