Terreic acid, shown below, is a naturally occurring antibiotic metabolite of the fungus Aspergillus terreus. Terreic acid hinders bacterial growth by covalently binding to (and thereby deactivating) the biosynthetic enzyme MurA, which is responsible for synthesizing the bacterial cell wall. In aqueous environments, terreic acid tautomerizes to a more stable enol form. Draw the two most stable enol tautomers of terric acid. Circle the tautomer above that you would expect to predominate inside a cellular environment.

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Chapter1: Chemical Foundations
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Terreic acid, shown below, is a naturally occurring antibiotic metabolite of
the fungus Aspergillus terreus. Terreic acid hinders bacterial growth by covalently binding
to (and thereby deactivating) the biosynthetic enzyme MurA, which is responsible for
synthesizing the bacterial cell wall. In aqueous environments, terreic acid tautomerizes to a
more stable enol form.
Draw the two most stable enol tautomers of terric acid.
Circle the tautomer above that you would expect to predominate inside a cellular
environment.
Transcribed Image Text:Terreic acid, shown below, is a naturally occurring antibiotic metabolite of the fungus Aspergillus terreus. Terreic acid hinders bacterial growth by covalently binding to (and thereby deactivating) the biosynthetic enzyme MurA, which is responsible for synthesizing the bacterial cell wall. In aqueous environments, terreic acid tautomerizes to a more stable enol form. Draw the two most stable enol tautomers of terric acid. Circle the tautomer above that you would expect to predominate inside a cellular environment.
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