Solid-phase synthesis of an apoptosis-inducing tetrapeptide mimicking the Smac protein

Sebastian Thordal Le Quement, Mette Ishøy, Mette Terp Petersen, Pernille Mansgaard Simonsen, Nanna S. Holck, Thomas Eiland Nielsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

An approach for the solid-phase synthesis of apoptosis-inducing Smac peptidomimetics is presented. Using a Rink linker strategy, tetrapeptides mimicking the N-4-terminal residue of the Smac protein [(N-Me)AVPF sequence] were synthesized on PEGA resin in excellent purities and yields. Following two synthetic routes, a known tetrapeptide, incorporating a substituted proline, previously shown to exhibit excellent biological activity in vitro as well as low toxicity, was synthesized effectively on a solid support.
Original languageEnglish
JournalTetrahedron Letters
Volume52
Issue number52
Pages (from-to)7049-7053
ISSN0040-4039
DOIs
Publication statusPublished - 2011

Keywords

  • Apoptosis
  • Peptides Smac mimetics
  • Solid-phase synthesis
  • Peptidomimetics

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