Published in
Elsevier, Bioorganic and Medicinal Chemistry Letters, 11(22), p. 3791-3794
DOI: 10.1016/j.bmcl.2012.04.003
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The macrocycle of leinamycin imparts hydrolytic stability to the thiol-sensing 1,2-dithiolan-3-one 1-oxide unit of the natural product
Journal article published in 2012 by
Santhosh Sivaramakrishnan,
Leonid Breydo 
,
Daekyu Sun,
Kent S. Gates
,
Daekyu Sun,
Kent S. Gates
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Abstract
Reaction of cellular thiols with the 1,2-dithiolan-3-one 1-oxide moiety of leinamycin triggers the generation of DNA-damaging reactive intermediates. Studies with small, synthetic analogues of leinamycin reveal that the macrocyclic portion of the natural product imparts remarkable hydrolytic stability to the 1,2-dithiolan-3-one 1-oxide heterocycle without substantially compromising its thiol-sensing property.