Lanthanide-mediated dephosphorylation used for peptide cleavage during solid phase peptide synthesis

Byunghee Yoo, Mark D. Pagel

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

Lanthanide(III) ions can accelerate the hydrolysis of phosphomonoesters and phosphodiesters in neutral aqueous solution. In this paper, lanthanide-mediated dephosphorylation has been applied in aqueous media as an orthogonal cleavage condition that can be employed in conventional solid phase peptide synthesis (SPPS). A phosphorylated polymeric support for SPPS was developed using Boc chemistry. The cleavage of resin-bound phosphates was investigated with the addition of Eu(III), Yb(III), acid or base, a mixture of solvents or different temperatures. To demonstrate the utility of this approach for SPPS, a peptide sequence was synthesized on a phosphorylated polymeric support and quantitatively cleaved with lanthanide ions in neutral aqueous media. The protecting groups for side chains were retained during peptide cleavage using lanthanide ions. This new methodology provides a mild orthogonal cleavage condition of phosphoester as a linker during SPPS.

Original languageEnglish (US)
Pages (from-to)3894-3905
Number of pages12
JournalMolecules
Volume18
Issue number4
DOIs
StatePublished - Apr 1 2013

Keywords

  • Dephosphorylation
  • Lanthanide
  • Peptide synthesis
  • Solid phase

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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