Issue 16, 2005

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

Abstract

Kinetics of the β-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 β-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 β-methyldehydroalanine residue was, in turn, observed to be a poor Michael acceptor.

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

Article information

Article type
Paper
Submitted
21 Apr 2005
Accepted
17 Jun 2005
First published
13 Jul 2005

Org. Biomol. Chem., 2005,3, 3039-3044

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

K. Mattila, J. Siltainsuu, L. Balaspiri, M. Ora and H. Lönnberg, Org. Biomol. Chem., 2005, 3, 3039 DOI: 10.1039/B505573C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements