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Date May 2009 Marks available 5 Reference code 09M.3.hl.TZ2.D4
Level HL Paper 3 Time zone TZ2
Command term Describe and Explain Question number D4 Adapted from N/A

Question

Antibacterials are drugs that kill or inhibit the growth of microorganisms that cause infectious diseases. The general structure of penicillin, an antibacterial, is given below.

M09/4/CHEMI/HP3/ENG/TZ2/D4

Describe the composition and structure of the beta-lactam ring in penicillin and explain its importance.

Markscheme

ring consists of one nitrogen atom and three carbon atoms (and three hydrogen atoms);

4 membered/square ring structure / bond angles of 90°;

ring under stress/strain / increased (chemical) reactivity / ring opens (due to angle of 90° instead of about 109°);

bonds to/blocks action of enzyme/transpeptidase;

reaction with the enzyme not reversible / prevents cross linking of peptides / inhibits synthesis and growth of bacterial cell walls / OWTTE;

Examiners report

Many candidates were unable to explain the importance of the beta-lactam ring in penicillin. The bonds in the opened structure blocks the action of the enzyme, transpeptidase, a non-reversible reaction that prevents cross linkage of peptides in the bacteria, which inhibits the synthesis and growth of bacterial cell walls.

Syllabus sections

Options » D: Medicinal chemistry » D.2 Aspirin and penicillin
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