History of penicillins: The first penicillin isolated by Alexander Fleming, known as penicillin F, is also called what?

Difficulty: Medium

Correct Answer: n-heptyl penicillin

Explanation:

Introduction / Context:Early penicillins were differentiated by the acyl side chain attached to the 6-aminopenicillanic acid nucleus. Historical nomenclature (Penicillin F, G, V, etc.) reflects distinct side chains and discovery chronology.

Given Data / Assumptions:

  • We must match “penicillin F” to its side chain name.
  • Common penicillins: G (benzyl), V (phenoxymethyl); others (K, F) have different alkyl/alkenyl side chains.

Concept / Approach:Penicillin F corresponds to an n-heptyl side chain. In contrast, penicillin G is benzyl penicillin and penicillin V is phenoxymethyl penicillin; 2-pentenyl penicillin aligns with other labeled variants (e.g., K), not F.

Step-by-Step Solution: Recall mapping: F → n-heptyl; G → benzyl; V → phenoxymethyl. Eliminate distractors that match G or V. Choose n-heptyl penicillin.

Verification / Alternative check:Reference tables of early penicillins list Penicillin F as n-heptyl based on side-chain analysis.

Why Other Options Are Wrong:

  • 2-Pentenyl: not Penicillin F.
  • Phenoxymethyl: Penicillin V.
  • Benzyl: Penicillin G.

Common Pitfalls:Assuming alphabetical letters map to common clinical penicillins only (G or V) and overlooking historic variants.

Final Answer:n-heptyl penicillin

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