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Org Lett. 2007 Mar 1;9(5):845-8. Epub 2007 Feb 3.

Biosynthetic convergence of salinosporamides A and B in the marine actinomycete Salinispora tropica.

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  • 1College of Pharmacy, University of Arizona, Tucson, Arizona 85721, USA.

Abstract

[structure: see text] Feeding experiments with stable isotopes established that the potent 20S-proteasome inhibitors salinosporamide A and B are biosynthesized in the marine bacterium Salinispora tropica from three biosynthetic building blocks, namely, acetate, beta-hydroxy-2'-cyclohexenylalanine, and either butyrate or a tetrose-derived chlorinated molecule. The unexpected observation that the chlorinated four-carbon residue in salinosporamide A is derived from a different metabolic origin than the non-chlorinated four-carbon unit in salinosporamide B is suggestive of a convergent biosynthesis to these two anticancer natural products.

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