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

TitleSynthesis of small cyclic peptides constrained with 3-(3-aminomethylphenyl)propionic acid linkers using free radical-mediated macrocyclization
Publication TypeJournal Article
Year of Publication2005
AuthorsBalraju, V, D. Reddy, S, Periasamy, M, Iqbal, J
JournalTetrahedron Letters
Volume46
Issue31
Pagination5207-5210
Date PublishedAUG
AbstractIn 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-AlBN 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 (gamma/beta-turn). (c) 2005 Published by Elsevier Ltd.
DOI10.1016/j.tetlet.2005.05.115
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.347
Divison category: 
Organic Chemistry