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

Protein Pept Lett. 2010 Jul;17(7):809-16. doi: 10.2174/092986610791306779.

Abstract

The cyclic peptide EGLNc Psi [CON((CH(2))(3)NH)pYNleE(NHCH(2)CO)]L-NH(2) (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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / chemistry
  • Amino Acids / metabolism
  • Chromatography, High Pressure Liquid
  • Fluorenes / chemistry
  • Fluorenes / metabolism
  • Models, Molecular
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / metabolism
  • Phosphotyrosine / chemistry*
  • Phosphotyrosine / metabolism
  • Protein Tyrosine Phosphatase, Non-Receptor Type 6 / chemistry*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 6 / metabolism
  • src Homology Domains*

Substances

  • Amino Acids
  • Fluorenes
  • N(alpha)-fluorenylmethyloxycarbonylamino acids
  • Peptides, Cyclic
  • Phosphotyrosine
  • Protein Tyrosine Phosphatase, Non-Receptor Type 6