S. Borman
Sep 27, 2004
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Chemical & Engineering News
Abstract
THIOSTREPTON, AN EXTRAordinarily complex bacterial natural product that's used as a topical veterinary antibiotic and also has promising antimalarial and anticancer activity, has yielded to total chemical synthesis. First isolated from bacteria in 1955, thiostrepton has an unusual type of antibiotic activity: It disables protein biosynthesis by binding to ribosomal RNA and one of its associated proteins. British crystallographer and 1964 Nobel Prize winner Dorothy Crowfoot Hodgkin solved the structure in 1970. Thiostrepton includes 10 rings, 11 peptide bonds, extensive unsaturation, and 17 stereogenic centers. More challenging still, it is highly acid-and base-sensitive. It's the parent compound and the most complex member of a family of thiopeptide antibiotics. Now, the compound has succumbed to the synthetic blandishments of chemistry professor K. C Nicolaou and coworkers at Scripps Research Institute and the University of California, San Diego [ Angew. Chem. Int. Ed. , 43 , 5087 and 5092 (2004)]. "It's...