A2 Vertaisarvioitu katsausartikkeli tieteellisessä lehdessä
Synthesis of bicyclic peptides
Tekijät: Karskela T, Virta P, Lonnberg H
Kustantaja: BENTHAM SCIENCE PUBL LTD
Julkaisuvuosi: 2006
Lehti:: Current Organic Synthesis
Tietokannassa oleva lehden nimi: CURRENT ORGANIC SYNTHESIS
Lehden akronyymi: CURR ORG SYNTH
Vuosikerta: 3
Numero: 3
Aloitussivu: 283
Lopetussivu: 311
Sivujen määrä: 29
ISSN: 1570-1794
DOI: https://doi.org/10.2174/157017906777934917
Tiivistelmä
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.
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.
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