Biochemistry—Peptide Bond Resonance Resonance structures drawn for the peptide bond imply which of the following?

Difficulty: Easy

Correct Answer: Both A and B.

Explanation:


Introduction / Context:
Peptide bond resonance is central to protein structure. Delocalization between the carbonyl and the amide nitrogen creates partial double-bond character and defines peptide planarity.


Given Data / Assumptions:

  • Resonance implies electron delocalization between C=O and C–N.
  • Partial double-bond character shortens and strengthens C–N relative to a single bond.
  • Restricted rotation yields a planar peptide unit.


Concept / Approach:
If resonance increases bond order above 1, the bond becomes stronger and less rotatable. Therefore both strengthening and partial double-bond character are correct.


Step-by-Step Solution:

Step 1: Consider resonance forms that place a double bond between C and N.Step 2: Infer consequences: shorter, stronger C–N bond with restricted rotation.Step 3: Choose the combined statement that includes both effects.


Verification / Alternative check:
Empirical peptide C–N bond lengths fall between typical single and double bonds, consistent with partial double-bond character.


Why Other Options Are Wrong:

  • D is incorrect; peptide bond electronic structure is well characterized.
  • E is incorrect; free rotation contradicts resonance-imposed planarity.


Common Pitfalls:
Assuming resonance only affects stability but not geometry; confusing φ/ψ mobility with peptide ω rigidity.


Final Answer:
Both A and B.

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