Synthesis of small cyclic peptides constrained with 3-(3-aminomethylphenyl)propionic acid linkers using free radical-mediated macrocyclization

Balraju, V. ; Srinivasa Reddy, D. ; Periasamy, Mariappan ; Iqbal, Javed (2005) Synthesis of small cyclic peptides constrained with 3-(3-aminomethylphenyl)propionic acid linkers using free radical-mediated macrocyclization Tetrahedron Letters, 46 (31). pp. 5207-5210. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/j.tetlet.2005.05.115

Related URL: http://dx.doi.org/10.1016/j.tetlet.2005.05.115

Abstract

In this letter, we report that small peptides (di- and tri-) having a 3-bromobenzyl group at the C-termini and an acryloyl group at the N-termini undergo an efficient Bu3SnH–AIBN mediated intramolecular free radical cyclization to afford cyclic peptides in good yields. We also propose that these cyclizations are occurring via a pre-organized acyclic structure dictated by a reverse turn (γ/β-turn).

Item Type:Article
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ID Code:122017
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