A highly efficient method for the preparation of phosphinic pseudodipeptidic blocks suitably protected for solid-phase peptide synthesis

Dimitris Georgiadis, Magdalini Matziari, Athanasios Yiotakis*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

Building blocks of the general type FmocXaaψ{PO(OAd)CH2}YaaOH suitable for solid-phase synthesis of phosphinic peptides have been prepared using a new synthetic strategy based on mild and high-yielding reactions. The key reaction of this method is the Michael addition of activated Fmoc protected silyl aminophosphonites to benzyl acrylates at room temperature. As compared to our previous work, this method consists of less synthetic steps and doubles the overall yield, thus providing a convenient route to phosphinic synthons suitable for the solid-phase preparation of inhibitors of various metalloproteases.

Original languageEnglish
Pages (from-to)3471-3478
Number of pages8
JournalTetrahedron
Volume57
Issue number16
DOIs
Publication statusPublished - 16 Apr 2001
Externally publishedYes

Keywords

  • Michael addition
  • Phosphinic peptides
  • Zinc metalloprotease inhibitors

Cite this