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Question #44960
The Question
Consider the rare keto-enol tautomerization of the purine base Guanine () within a deoxyribonucleotide residue in a DNA strand at and physiological pH. Evaluate the following statements regarding its stereoelectronic properties and structural geometry:
I. In the enol tautomer (), the N1 atom transitions from a hydrogen bond donor to a hydrogen bond acceptor due to proton migration to the C6 oxygen. II. forms a stable mispair with Thymine () because the altered hydrogen-bonding profile perfectly complements the N3-H donor and C4=O acceptor of Thymine. III. The tautomeric shift alters the dipole moment and effective pairing distance, inducing a conformational shift of the -N-glycosidic linkage towards the \textit{syn} geometry to alleviate steric hindrance with the sugar-phosphate backbone. IV. The standard Gibbs free energy change () for the transition is highly negative, which drives the spontaneous formation of Z-DNA.
Which of the given statements are correct?
Options
- A.
I, II, and III
- B.
I and II only
- C.
II, III, and IV
- D.
I, III, and IV
Check Your Answer
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
Glycosidic Linkage Geometry|Nucleoside vs Nucleotide|Nitrogenous Base Keto-Enol Tautomerism
Why This Question Is Tricky
Common Mistakes
Students typically memorize that purines in B-DNA are strictly in the anti conformation and that tautomerization merely causes a base-pair substitution (wobble pairing) without affecting the backbone geometry.
The 'Hidden Variable' being tested is the stereochemical consequence of the tautomeric shift: the migration of the proton alters the dipole moment and the spatial requirements of the base pair.
This forces a rotation around the -N-glycosidic bond (towards the syn conformation) to relieve steric strain with the sugar-phosphate backbone while maintaining the necessary hydrogen-bonding distance for the -T mispair.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Biomolecules - Class 12 |
| Concept | Glycosidic Linkage Geometry |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |