Mapping the X(+1) binding site of the Grb2-SH2 domain with alpha,alpha-disubstituted cyclic alpha-amino acids

Bioorg Med Chem Lett. 1999 Oct 18;9(20):2915-20. doi: 10.1016/s0960-894x(99)00501-6.

Abstract

A series of phosphopeptides containing alpha,alpha-disubstituted cyclic alpha-amino acids (Ac(n)c, 3 < or = n < or = 7; n refers to the number of carbons in the ring) at the X(+1) position of Ac-Tyr(PO3H2)-X(+1)-Asn-NH2 has been synthesised and their inhibitory activity as antagonists of the Grb2-SH2 domain has been determined in competitive binding assays. The SAR data obtained have been interpreted by using models constructed from the X-ray structure of the ligand-bound Grb2-SH2 domain. The used of alpha,alpha-disubstituted cyclic alpha-amino acids to map the binding pockets of proteins expands the classical alanine scan concept and takes advantage of the known conformational preferences of these amino acids.

MeSH terms

  • Adaptor Proteins, Signal Transducing*
  • Amino Acids, Cyclic / chemistry
  • Amino Acids, Cyclic / metabolism*
  • Binding Sites
  • GRB2 Adaptor Protein
  • Models, Molecular
  • Proteins / chemistry
  • Proteins / metabolism*
  • src Homology Domains*

Substances

  • Adaptor Proteins, Signal Transducing
  • Amino Acids, Cyclic
  • GRB2 Adaptor Protein
  • Proteins