Detection and minimization of H-phosphonate side reaction during phosphopeptide synthesis by a post-assembly global phosphorylation strategy

Qinghong Xu, Elizabeth A. Ottinger, Nuria A. Solé, George Barany

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

In the course of solid-phase synthesis of phosphopeptides by a post-assembly global phosphorylation strategy, the corresponding H-phosphonate peptides form as byproducts. We describe model studies to investigate this side reaction as a function of reaction conditions, and use this information to develop conditions that minimize the problem, i.e., use of dibenzyl N,N-di-isopropyl phosphoramidite for phosphitylation, followed immediately by oxidation with anhydrous tert-butyl hydroperoxide in dry tetrahydrofuran under argon, and final acidolytic cleavage.

Original languageEnglish (US)
Pages (from-to)333-342
Number of pages10
JournalLetters in Peptide Science
Volume3
Issue number6
StatePublished - 1996

Keywords

  • Gel-phase nuclear magnetic resonance
  • H-phosphonate byproduct
  • Phosphopeptides
  • Phosphoramidite chemistry
  • Post-assembly phosphorylation
  • Solid-phase peptide synthesis

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