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Question #44984

Difficulty: 8/10 | 🟢 Free

The Question

During DNA replication at 298 K298\text{ K}, Thymine (TT) typically exists in the lactam (keto) form and pairs with Adenine. However, a spontaneous point mutation can occur if TT undergoes tautomerization to its rare lactim (enol) form (T∗T^*), where the proton from N3 migrates to O4. In this T∗T^* form, it mispairs with a different standard nitrogenous base YY from the nucleotide pool.

Given that the pKapK_a of the N3-H proton in standard Thymine is 9.89.8, determine the following four parameters in order:

  1. The identity of the mispaired base YY.
  2. The total number of hydrogen bonds formed in the T∗≡YT^* \equiv Y base pair.
  3. The number of hydrogen bond DONORS provided specifically by T∗T^* in this base pair.
  4. The net charge on the dominant species of standard Thymine at an alkaline pH of 11.811.8.

Options

  • A.

    Guanine, 3, 1, -1

  • B.

    Guanine, 2, 1, 0

  • C.

    Cytosine, 3, 2, -1

  • D.

    Adenine, 2, 0, -1

Check Your Answer

Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Exception_Exposure

Learn to identify edge cases and boundary exceptions that JEE examiners hide in math problems.

Concepts Behind This Question

Base Pairing Stability|Nitrogenous Base Keto-Enol Tautomerism|Amino Acid Zwitterion pH Sensitivity

Why This Question Is Tricky

Common Mistakes

The question tests the student's ability to move beyond the static Watson-Crick base-pairing model and apply electronic effects (keto-enol tautomerism) to macromolecular stability.

Students often memorize that Thymine pairs with Adenine via 2 H-bonds.

The 'trap' is failing to recognize how the tautomeric shift alters the specific H-bond donor/acceptor topography (N3 becomes an acceptor, O4 becomes a donor), which makes T∗T^* an isosteric mimic of Cytosine, thermodynamically favoring pairing with Guanine via 3 H-bonds.

Additionally, it tests the application of ionic equilibrium to determine the dominant ionization state of the nitrogenous base at a given pH, challenging the assumption that DNA bases are always neutral.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterBiomolecules - Class 12
ConceptBase Pairing Stability
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree