The antitumor antibiotic mitomycin C functions by forming cross-links in DNA chains. (a) The first step is

Question:

The antitumor antibiotic mitomycin C functions by forming cross-links in DNA chains.

(a) The first step is loss of methoxide and formation of an iminium ion intermediate that is deprotonated to give an enamine. Show the mechanism.

(b) The second step is reaction of the enamine with DNA to open the three-membered, nitrogen-containing (aziridine) ring. Show the mechanism.

(c) The third step is loss of carbamate (NH₂CO^?) and formation of an unsaturated iminium ion, followed by a conjugate addition of another part of the DNA chain. Show the mechanism.

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Organic Chemistry

ISBN: 9780495112587

7 Edition

Authors: John McMurry

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Question Posted: Mar 08, 2011 04:38 AM

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The antitumor antibiotic mitomycin C functions by forming cross-links in DNA chains. (a) The first step is

Question:

NH2 C-NH2 H2N-DNA H2N. OCH3 H2N. H2N-DNA -сн-он NH N. NH Hзс HзС H. H. Mitomycin C Enamine -NH2 H2N-DNA- -N-DNA H2N. H2N. N-DNA N-DNA Нэс Нзс NH2 "NH2

Step by Step Answer:

a HN HC HN H3C Mitomycin C b enamine HN OCH3 HN HN HN ...View the full answer

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