Chapter 6: Problem 5

Draw a mechanism for the intrastrand cross linkage of two guanines by busulfan \((6.33, n=4)\).

Short Answer

Expert verified

Busulfan cross-links two adjacent guanine bases by reacting with their N7 positions, forming a monoadduct with the first guanine, attracting the adjacent guanine base to form a cross-linked intermediate, and finally reacting with the second guanine to complete the cross-linking. In the process, two methanesulfonate ions are released.

Step by step solution

Reaction of busulfan with the first guanine

The reaction starts when busulfan, a bifunctional alkylating agent, reacts with the N7 position of the first guanine base. This reaction results in the formation of a sulfur-nitrogen bond and leaves the sulfur atom on busulfan with a positive charge. In the process, a methanesulfonate ion is released from busulfan. As a result of this reaction, a monoadduct is formed.

Formation of cross-linked intermediate

In the next step, a sulfonium ion intermediate is formed. This happens when the positively charged sulfur atom in the monoadduct attracts the negatively charged electron cloud of the adjacent guanine base's N7 position.

Reaction with the second guanine

Finally, the positively charged sulfur atom reacts with N7 position of the second guanine, forming another sulfur-nitrogen bond and releasing another methanesulfonate ion. At this point, the two guanine bases are cross-linked, completing the reaction.

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Draw a mechanism for the intrastrand cross linkage of two guanines by busulfan \((6.33, n=4)\).

Short Answer

Step by step solution

Reaction of busulfan with the first guanine

Formation of cross-linked intermediate

Reaction with the second guanine

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