Asn102 of the gonadotropin-releasing hormone receptor is a critical determinant of potency for agonists containing C-terminal glycinamide

J Biol Chem. 1996 Jun 28;271(26):15510-4. doi: 10.1074/jbc.271.26.15510.

Abstract

We demonstrate a critical role for Asn102 of the human gonadotropin-releasing hormone (GnRH) receptor in the binding of GnRH. Mutation of Asn102, located at the top of the second transmembrane helix, to Ala resulted in a 225-fold loss of potency for GnRH. Eight GnRH analogs, all containing glycinamide C termini like GnRH, showed similar losses of potency between 95- and 750-fold for the [Ala102]GnRHR, compared with wild-type receptor. In contrast, four GnRH analogs that had ethylamide in place of the C-terminal glycinamide residue, showed much smaller decreases in potency between 2.4- and 11-fold. In comparisons of three agonist pairs, differing only at the C terminus, glycinamide derivatives showed an 11-20-fold greater loss of potency for the mutant receptor than their respective ethylamide derivatives. Thus Asn102 is a critical determinant of potency specifically for ligands with C-terminal glycinamide, while ligands with C-terminal ethylamide are less dependent on Asn102. These findings indicate a role for Asn102 in the docking of the glycinamide C terminus and are consistent with hydrogen bonding of the Asn102 side chain with the C-terminal amide moiety. Taken with previous data, they suggest a region of the GnRH receptor formed by the top of helices 2 and 7 as a binding pocket for the C-terminal part of the ligand.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Asparagine / chemistry*
  • Binding Sites
  • Glycine / analogs & derivatives
  • Glycine / chemistry
  • Gonadotropin-Releasing Hormone / chemistry*
  • Humans
  • Inositol Phosphates / metabolism
  • Ligands
  • Molecular Sequence Data
  • Mutagenesis, Site-Directed
  • Oligodeoxyribonucleotides / chemistry
  • Protein Binding
  • Protein Structure, Tertiary
  • Receptors, LHRH / chemistry*
  • Signal Transduction
  • Structure-Activity Relationship

Substances

  • Inositol Phosphates
  • Ligands
  • Oligodeoxyribonucleotides
  • Receptors, LHRH
  • Gonadotropin-Releasing Hormone
  • glycine amide
  • Asparagine
  • Glycine