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Question #45098

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The Question

The spontaneous mutation of DNA is often attributed to the transient formation of rare tautomers of nucleobases. Consider the tautomerization of Adenine (A) to its rare imino form (A∗A^*) at 298 K and physiological pH. In its standard amino form, Adenine pairs with Thymine (T) via two hydrogen bonds, where N1 acts as an acceptor and N6 acts as a donor. When A∗A^* is incorporated during DNA replication, it forms a stable mispair that preserves the standard purine-pyrimidine Watson-Crick geometry. Which of the following correctly identifies the mispaired nucleobase and the altered hydrogen-bonding roles of N1 and N6 in A∗A^*?

Options

  • A.

    Cytosine; N1 (A∗A^*) acts as H-bond donor, N6 (A∗A^*) acts as H-bond acceptor

  • B.

    Cytosine; N1 (A∗A^*) acts as H-bond acceptor, N6 (A∗A^*) acts as H-bond donor

  • C.

    Guanine; N1 (A∗A^*) acts as H-bond donor, N6 (A∗A^*) acts as H-bond acceptor

  • D.

    Thymine; N1 (A∗A^*) acts as H-bond donor, N6 (A∗A^*) acts as H-bond acceptor

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Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Mechanism_Trap

Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.

Concepts Behind This Question

Tautomerism Conditions|Base Pairing Stability

Why This Question Is Tricky

Common Mistakes

The question tests the intersection of heterocyclic tautomerism and supramolecular chemistry (hydrogen bonding).

The 'Hidden Variable' is the stereoelectronic consequence of the amino-imino proton shift: students often fail to recognize that protonating N1 forces the exocyclic N6 imino group to present its lone pair (acting as an acceptor) to the Watson-Crick interface to avoid a severe steric clash with the newly formed N1-H.

This inversion of the donor/acceptor profile dictates the highly specific, non-canonical pairing with Cytosine, illustrating the chemical basis of spontaneous mutagenesis.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterOrganic Chemistry – Some Basic Principles and Techniques - Class 11 Part 2
ConceptTautomerism Conditions
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree