Synthetic strategies to a backbone-side chain cyclic SHP-1 N-SH2 ligand containing N-functionalized alkyl phosphotyrosine

Kathleen Teichmann, Tobias Niksch, Karin Wieligmann, Martin Zacharias, Diana Imhof

Research output: Contribution to journalArticlepeer-review

Abstract

The cyclic peptide EGLNcΨ[CON((CH2)3NH)pYNleE(NHCH2CO)]L-NH2 (1) was designed and synthesized according to a native interaction partner of tyrosine phosphatase SHP-1. We introduced N-aminopropyl-phosphotyrosine to enable backbone-side chain cyclization with a glutamic acid derivative as counterpart for cyclization. Different approaches have been compared to find a strategy for the generation of backbone and backbone-side chain cyclic phosphopeptides.

Original languageEnglish
Pages (from-to)809-816
Number of pages8
JournalProtein and Peptide Letters
Volume17
Issue number7
DOIs
StatePublished - 2010
Externally publishedYes

Keywords

  • Backbone cyclization
  • Ligand
  • N-functionalized alkyl phosphotyrosine
  • Protein tyrosine phosphatase
  • SH2 domain
  • SHP-1

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