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Question #44984
The Question
During DNA replication at , Thymine () typically exists in the lactam (keto) form and pairs with Adenine. However, a spontaneous point mutation can occur if undergoes tautomerization to its rare lactim (enol) form (), where the proton from N3 migrates to O4. In this form, it mispairs with a different standard nitrogenous base from the nucleotide pool.
Given that the of the N3-H proton in standard Thymine is , determine the following four parameters in order:
- The identity of the mispaired base .
- The total number of hydrogen bonds formed in the base pair.
- The number of hydrogen bond DONORS provided specifically by in this base pair.
- The net charge on the dominant species of standard Thymine at an alkaline pH of .
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 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
| Subject | Chemistry |
| Chapter | Biomolecules - Class 12 |
| Concept | Base Pairing Stability |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |