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Synfacts 2006(1): 0014-0014  
DOI: 10.1055/s-2005-921667
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Thiostrepton

Contributor(s): Philip Kocienski
K. C. Nicolaou*, B. S. Safina, M. Zak, S. H. Lee, M. Navalainen, M. Bella, A. A. Estrada, C. Funke, F. J. Zecri, S. Bulat
The Scripps Research Institute, La Jolla, USA
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Publikationsverlauf

Publikationsdatum:
16. Dezember 2005 (online)

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Significance

Thiostrepton, a thiopeptide anti­biotic of Stretomyces azureus and related species, binds to ribosomal RNA and protein L11 and thereby inhibits GTPase-dependent processes. Acid- and base-sensitivity were major hurdles in the synthesis of Thiostrepton with its functional and stereochemical complexity (10 rings, 17 stereogenic centers, a 26-membered ring and a 27-membered ring).