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Penicillin

Penicillin. 1928: Alexander Fleming noticed that a mould ( penicillium notatum ) produced a compound that inhibits bacterial growth. 1940: Florey and Chain showed that an injection of extract cured infections in mice and later in humans.

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Penicillin

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  1. Penicillin

  2. 1928: Alexander Fleming noticed that a mould (penicillium notatum) produced a compound that inhibits bacterial growth. • 1940: Florey and Chain showed that an injection of extract cured infections in mice and later in humans. • 1945: Fleming, Florey and Chain were awarded a Nobel Prize for Medicine.

  3. Penicillin-G

  4. Penicillin works by inhibiting an enzyme involved in the building of bacterial cell walls.

  5. The mould extract was broken down if taken by mouth and effective only against a limited range of bacteria. In the 1950s it was shown that penicillin-G could be broken down to give 6-amino penicinillic acid from which a range of semi- synthetic penicillins could be made.

  6. 6-APA

  7. Unfortunately penicillins are fragile What is the bond angle here ? What does it “want” to be ? How can it get there ?

  8. Bacteria that have the enzyme β-lactamase can hydrolyse the strained amide group. These are resistant. Why does this resistance spread? Suggest 2 ways of overcoming this resistance.

  9. Make a penicillin that does not fit into the active site of β-lactamase : Methacillin 2) Inhibit β-lactamase by mixing the active penicillin with Clavulanic acid

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