Paz Castañal, Manuel María2021-08-192021-08-192010Proceedings of the 14th International Electronic Conference on Synthetic Organic Chemistry, 1–30 November 2010, MDPI: Basel, Switzerland, doi:10.3390/ecsoc-14-004833-906980-24-3http://hdl.handle.net/10347/26883The 14th International Electronic Conference on Synthetic Organic Chemistry session Natural Products ChemistryWe report that the clinically used antitumor drug mitomycin C reacts with excess dithiols to give dithiol cross-links as major products. Mechanistic studies reveal that three dithiol molecules participate at different stages of the reaction: in the reductive activation of mitomyicin C, in an alkylation at C1, and in an additional reduction that activates C10 for the second-arm alkylation by the dithiol. We hypothesize that the reactions reported here indicate that mitomycin C could act as a mechanism-based inhibitor of enzymes containing a dithiol active siteeng© 2010 The author(s). Published by MDPI, Basel, Switzerland. Open Accessbook part10.3390/ecsoc-14-00483open access