Synthesis of galmic: A nonpeptide galanin receptor agonist

S. C. Ceide, Laurent Alain Claude Trembleau, G. Haberhauer, L. Somogyi, T. Bartfai, J. Rebek Jnr

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Abstract

Galanin is a neuropeptide with a wide variety of biological functions. Few nonpeptide ligands, capable of activating galanin receptors, are available today. Based on known pharmacophores of galanin and the tripeptidomimetic galnon, a combinatorial library was formulated, synthesized, and screened against the galanin receptor. An active compound, galmic, was identified and tested in vitro and in vivo for its affinity and efficacy at galanin receptors. The present work describes the total synthesis of galmic, the synthesis of its oxazole precursors, the coupling of the building blocks into a linear trimer, and the macrolactamization reaction.

Original languageEnglish
Pages (from-to)16727-16732
Number of pages5
JournalPNAS
Volume101
Issue number48
DOIs
Publication statusPublished - 2004

Keywords

  • galnon
  • mimetic
  • MARINE NATURAL-PRODUCTS
  • PEPTIDES
  • NEUROPEPTIDE
  • BEHAVIORS
  • SUBTYPES
  • NUCLEUS
  • PAIN

Cite this

Ceide, S. C., Trembleau, L. A. C., Haberhauer, G., Somogyi, L., Bartfai, T., & Rebek Jnr, J. (2004). Synthesis of galmic: A nonpeptide galanin receptor agonist. PNAS, 101(48), 16727-16732. https://doi.org/10.1073/pnas.0407543101