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ExamsJEE AdvancedChemistry

How many chiral centres are present in the structure of penicillin G (benzylpenicillin)?

  1. 1
  2. 2
  3. 3
  4. 4

Correct answer: 3

Solution

Penicillin G (benzylpenicillin) contains a bicyclic system consisting of a four-membered beta-lactam ring fused to a five-membered thiazolidine ring. The three chiral carbons are: C-3 (the carbon bearing the carboxylate group in the thiazolidine ring), C-5 (the carbon at the ring fusion bearing H and N), and C-6 (the carbon bearing the amide side chain on the beta-lactam ring). All three have four distinct substituents, making them stereocentres. The natural configuration is 2S,5R,6R (using IUPAC numbering).

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