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Chapter 6: Problem 8

\(N, N\)-Diethylnitrosoamine (4) is carcinogenic, resulting in ethylation of DNA. Two other products formed are acetaldehyde and \(\mathrm{N}_{2}\). Under anaerobic conditions or in the absence of NADPH no carcinogenicity is observed. Draw a mechanism for DNA ethylation by this compound.

Short Answer

Expert verified
The problem does not require a subtractive data output, rather a drawn mechanism. The carbon attachment to the DNA (methylation) consists of initiator, propagator and terminator steps. The notable characters are \(\mathrm{N}_{2}\) gas and acetaldehyde byproducts.

Step by step solution

01

Understand \(N, N\)-Diethylnitrosoamine Structure

First, we need to familiarize ourselves with the structure of \(N, N\)-Diethylnitrosoamine, which consists of a nitroso group (NO) attached to an amine group (NH2), and both nitrogen atoms are further attached to an ethyl group (C2H5).
02

Initiation

In the first step of the reaction, one of the \(N-C\) bonds in the diethylnitrosoamine molecule cleaves, due to either a light or heat source. This is the initiation step, which results in the formation of a diazoalkane and a nitrogen radical.
03

Generation of Ethyl Radical

In the next step, the nitrogen radical withdraws an electron from NADPH, generating NADP+ and a nitrogen molecule (\(\mathrm{N}_{2}\)). The N2 goes off as a byproduct, and the diazoalkane molecule from the previous step loses a nitrogen molecule generating an ethyl radical.
04

Ethylation of DNA

The ethyl radical thus formed is highly reactive and it attacks the DNA, abstracting a hydrogen atom and bonding with the DNA molecule, resulting in the ethylation of the DNA.
05

Recognize Byproducts

Finally, when the ethyl hydrogen salt reacts with water, acetaldehyde is produced.

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Most popular questions from this chapter

Show how isoguanosine (1) could form a Watson-Crick base pair with isocytidine (2).

Draw a mechanism for how kedarcidin (6) might act as an antitumor agent (a reducing agent is required).

Alkylating agents are used in cancer chemotherapy to interfere with DNA biosynthesis or replication. Why can these be useful considering that normal cells also need DNA?

Draw a mechanism for the formation of a 1,4 -benzene diradical from an activated enediyne (Bergman rearrangement).

It was proposed that a common mechanism for antibiotics might be hydroxyl radical oxidation of guanine to 7,8 -dihydro-8-oxoguanine (7), which is enzymatically excised from DNA and replaced by guanine; however, when too many guanines are oxidized, DNA strand breakage occurs, killing the cell. Draw a mechanism for how guanine could be oxidized by hydroxyl radicals to 7 .
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