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 language | English |
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Pages (from-to) | 274-282 |
Number of pages | 9 |
Journal | Biopolymers |
Volume | 84 |
Issue number | 3 |
DOIs | |
State | Published - 2006 |
Keywords
- Heck macrocyclization
- Microwave energy
- Peptidomimetics
- RGD sequence