Draw the mechanism of the hydration and the enol ketone tautomerization reaction using one of the alkynes in calicheamicin. Use the formal arrow pushing formalism and show the product of this hydration.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Draw the mechanism of the hydration and the enol ketone tautomerization reaction using one of the alkynes in calicheamicin. Use the formal arrow pushing formalism and show the product of this hydration.

но.
OH
о он
но-
НО.
OH
но/,
н
T
enedlyne
ОН
Bergman
Cyclisation
Heat
НО-
но-
OH
ном
OH
-О-Н-
НО-
+ damaged DNA
но
Proton abstraction
from DNA
backbone with
reactive radicals
н
4-didehydrobenzene
diradical product
Transcribed Image Text:но. OH о он но- НО. OH но/, н T enedlyne ОН Bergman Cyclisation Heat НО- но- OH ном OH -О-Н- НО- + damaged DNA но Proton abstraction from DNA backbone with reactive radicals н 4-didehydrobenzene diradical product
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