AAMC official section bank, chem/phys #40

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jeffbassett87
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AAMC official section bank, chem/phys #40

Post by jeffbassett87 » Fri Jun 05, 2020 8:47 pm

I need help understanding this.
NS_Tutor_Yuqi
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Re: AAMC official section bank, chem/phys #40

Post by NS_Tutor_Yuqi » Sat Jun 06, 2020 4:09 pm

From the first paragraph of the passage, we know that the enzyme catalyzes the hydrolysis of the peptide bond. The carbon that the question is referring to is therefore the C=O carbon that is part of the amide bond. In this initial state, carbon is in an sp2 state since it is double bonded to O and single bonded to N and another C. The passage later says that a deprotonated water on the enzyme attacks the substrate, which would be a nucleophilic attack and result in an sp3 state in the intermediate step. Lastly, the amine is removed as the final step of the hydrolysis reaction, which returns the carbon to its original sp2 state.
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