Biochemistry—Peptide Bond Cis/Trans Preference Which statement about peptide bond conformation is most accurate?

Difficulty: Easy

Correct Answer: Peptide bonds are usually trans; X–Pro bonds show a higher fraction of cis than others.

Explanation:


Introduction / Context:
Most peptide bonds adopt the trans configuration to minimize steric clashes across the peptide bond. This question probes knowledge of the special case involving proline.


Given Data / Assumptions:

  • Resonance restricts rotation, making peptide bonds planar.
  • Trans configuration is overwhelmingly favored for most residues.
  • X–Pro bonds have a notable minority population of cis compared with other residues.


Concept / Approach:
Recognize the general rule (trans) and the exception (X–Pro shows more cis than usual). Select the option that captures both ideas without overstating cis prevalence.


Step-by-Step Solution:

Step 1: Establish the baseline: peptide bonds are usually trans.Step 2: Consider the exception: proline's ring reduces the trans–cis energy gap, increasing the cis fraction.Step 3: Choose the statement that includes both truths.


Verification / Alternative check:
Protein structure statistics show cis is rare overall, but enriched at X–Pro positions compared with others.


Why Other Options Are Wrong:

  • “Usually cis” is false.
  • Planarity is due largely to resonance, not merely steric hindrance.
  • Only between prolines: false.
  • Nonplanar and freely rotating: contradicts resonance constraints.


Common Pitfalls:
Interpreting the special case as the rule; confusing φ/ψ flexibility with ω rigidity.


Final Answer:
Peptide bonds are usually trans; X–Pro bonds show a higher fraction of cis than others.

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