The Versatility of Selenium

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Science  07 Apr 2000:
Vol. 288, Issue 5463, pp. 13
DOI: 10.1126/science.288.5463.13h

Natural products provide an excellent starting point for the development of libraries of related molecules, which can be screened for biological activity, but the creation of combinatorial libraries can pose synthetic challenges. Chemical libraries usually are made by solid-phase synthesis, which requires a well-behaved linker between the molecular skeleton and the solid support, a tether that will survive subsequent reactions but can be cleaved readily upon completion.

In a pair of papers, Nicolaou et al. document the use of selenium-based chemistry for constructing libraries. Vancomycin, currently the antibiotic of last resort in the treatment of multidrug-resistant infections, can be coupled to a linker (that is versatile enough to link to carboxylic acids, alcohols, and amines) that allows for modifications to its critical oligosaccharide unit. Everninomicin, a promising new weapon against drug-resistant bacteria, contains 2-deoxy glycosides and orthoesters; selenium resins can be used for general stereoselective syntheses of these moieties and of the related allyl orthoesters, furnishing the building blocks for tinkering with this natural product.—JU

Angew. Chem. Int. Ed.39, 1084 (2000); Angew. Chem. Int. Ed.39, 1089 (2000).

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