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Synthesis and bioactivity of lincomycin 2-monoesters.

A homologous series of straight-chain lincomycin 2-monoesters, comprised of both acyl and carbonate esters, was synthesized. Good antibacterial activity was observed with esters of chain lengths from C4 to C16. Esters with chain lengths from C12 to C16 are tasteless and highly active in vivo in mice infected with Staphylococcus aureus. The carbonate esters show essentially the same taste and bioactivity as the acyl esters. The long-chain lincomycin 2-esters appear to have the desired properties required for formulation as a tasteless pediatric preparation.