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Date May 2017 Marks available 2 Reference code 17M.3.sl.TZ1.21
Level SL Paper 3 Time zone TZ1
Command term Outline Question number 21 Adapted from N/A

Question

Antiviral drugs are designed to take different approaches to fighting viruses.

Outline how oseltamivir (Tamiflu®) works.

[2]
a.

Oseltamivir was commercially produced from shikimic acid, a precursor which is a metabolite in micro-organisms and plants.

Outline how green chemistry was used to develop the precursor for oseltamivir in order to overcome a shortage of the drug during the flu season.

[2]
b.

Suggest why the administration of antibiotics to humans and animals can affect the environment.

[1]
c.

Markscheme

«drug» blocks/inhibits «viral» enzyme/neuraminidase/NA «activity»

prevents virus from leaving/escaping host cells «thus cannot infect other cells»

[2 marks]

a.

ALTERNATIVE 1:
«using» genetically modified/GM E. Coli/bacteria/microorganisms

E. Coli/bacteria biosynthesis
OR
E. Coli/bacteria «overfed by glucose» undergo fermentation
OR
cells of the bacteria «are broken down to» form precursor/shikimic acid

ALTERNATIVE 2:
use readily available cyclic ester/lactone

forms «the correct stereoisomer of oseltamivir» in a shorter number of chemical steps

 

Do not accept “planting more Chinese star anise” or “other plant sources of shikimic acid”.

[2 marks]

b.

«can develop antibiotic» resistance in bacteria/microorganisms
OR
changes in microbial/bacterial population

 

Accept secondary effects, such as reduced biodiversity of aquatic/soil ecosystems, denitrification of soil (due to decline in nitrogen-fixing bacteria). No mark for just stating “water contamination”.

No mark for just stating “failure of aquatic/marine environment”.

[1 mark]

c.

Examiners report

[N/A]
a.
[N/A]
b.
[N/A]
c.

Syllabus sections

Options » D: Medicinal chemistry » D.5 Anti-viral medications
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Options » D: Medicinal chemistry
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