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Synthesis of an Analog of the Novel Anti-neoplastic Agent Leinamycin

From an interview with Ted Tarkow, Professor of Classical Studies & Associate Dean of Arts & Science

Andrea Hicks, Chemistry

Kent Gates, Mentor

Leinamycin is a potent anti-tumor antibiotic that was isolated from a culture of Streptomyces in 1989. The unique compound features a 1,2-Dithiolan-3-one 1-oxide heterocycle which can cause DNA damage through multiple pathways. Hydrolysis t ½ of previous leinamycin analogs containing only the 1,2-Dithiolan-3-one 1-oxide group was approximately two hours, as compared to twenty-seven hours for leinamycin. The purpose of this project is to synthesize the leinamycin analog. This compound will be used to investigate the effect of a leinamycin-like vicinal amide group on the hydrolysis half-life of the 1,2-dithiolan-3-one-1-oxide.