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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Synthesis of Bicyclic Peptides

Author(s): Tuomas Karskela, Pasi Virta and Harri Lonnberg

Volume 3, Issue 3, 2006

Page: [283 - 311] Pages: 29

DOI: 10.2174/157017906777934917

Price: $65

Abstract

Bicyclic peptides have received interest as anticancer agents, protease inhibitors, antibiotics, receptor antagonists, artificial receptors and models of various structural motives of proteins. Their common characteristic feature, limited conformational freedom of the backbone, plays a central role in all these applications. The same feature poses a challenge for synthetic organic chemists. Additional levels have to be included in the protecting group strategy to ensure the desired regioselectivity of cyclization and still the yields tend to be low, owing to increasing rigidity that cyclizations, in particular the second one, result in. The present review is aimed at summarizing the strategies described for the synthesis of various types of bicyclic peptides, originally in solution-phase and nowadays more often on a solid-support.

Keywords: Solid-phase synthesis., bicyclic peptides, protecting groups, cyclization, peptide coupling


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