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. Author manuscript; available in PMC: 2020 Jun 18.
Published in final edited form as: Chemistry. 2010 Nov 22;16(44):13020–13029. doi: 10.1002/chem.201001562

Scheme 1.

Scheme 1.

Structure of leinamycin (9) and activation by thiols to the episulfonium ion (10), which is either attacked by guanine N7 followed by base excision to give adduct 11 (red arrows) or undergoes intramolecular attack to produce the epoxide 12 (black arrows). The labile moiety is shown in red, while the reactive species is shown in blue.