Fast and versatile microwave-assisted intramolecular heck reaction in peptide macrocyclization using microwave energy

Gerardo Byk, Mirit Cohen-Ohana, Daniel Raichman

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

We have revisited the intramolecular Heck reaction and investigated the microwave-assisted macrocyclization on preformed peptides using a model series of ring-varying peptides acryloyl-Gly-[Gly]n-Phe(4-I)NHR; n = 0-4. The method was applied to both solution and solid supported cyclizations. We demonstrate that the intramolecular Heck reaction can be performed in peptides both in solution and solid support using a modified domestic microwave within 1 to 30 minutes in DMF under reflux with moderate yields ranging from 15 to 25% for a scale between 2-45 mg of linear precursors. The approach was applied to the synthesis of a constrained biologically relevant peptidomimetic bearing an Arg-Gly-Asp (RGD) sequence. These results make the microwave-assisted Heck reaction an attractive renovated approach for peptidomimetics.

Original languageEnglish
Pages (from-to)274-282
Number of pages9
JournalBiopolymers
Volume84
Issue number3
DOIs
StatePublished - 2006

Keywords

  • Heck macrocyclization
  • Microwave energy
  • Peptidomimetics
  • RGD sequence

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