Solid-phase synthesis of new saphenamycin analogues with antimicrobial activity

Jane B. Laursen, P.C. de Visser, H.K. Nielsen, Knud Jørgen Jensen, John Nielsen

Research output: Contribution to journalJournal articleResearchpeer-review


An array of 12 new saphenamycin analogues modified at the benzoate moiety was synthesized on solid support. Synthesis commenced with a chemoselective anchoring of saphenic acid through the carboxyl group to a 2-chlorotrityl functionalized polystyrene resin. The secondary alcohol was acylated in parallel with a series of differently substituted benzoic acid derivatives. Treatment with TFA-CH2Cl2 (5:995) released the expected saphenamycin analogues into solution. These new analogues were purified, characterized and screened for antimicrobial activity against Bacillus subtilis and Proteus mirabilis. Eight analogues exhibited MIC values against B. subtilis ranging from 0.07 to 3.93 mug/mL, comparable to the activities of previously reported saphenamycin analogues.
Original languageEnglish
JournalBioorganic & medicinal chemistry letters
Issue number2
Pages (from-to)171-175
Publication statusPublished - 2002


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