Paxlovid is treatment for COVID-19 that was recently approved for use because it can drastically reduce the risk for hospitalization and death when taken early in the infection. It is actually a package of two different antiviral drugs. One of those is Nirmatrelvir, which is a modified tripeptide protein mimetic designed to covalently bind to and inhibit the main protease (MPro) from the SARS-CoV-2 virus. This protease recognizes and hydrolyzes peptide bonds at specific points in their sequence, and it is essential for viral replication. a. Below is one of the sequences that Mpro recognizes and cleaves. It cleaves the peptide bond between the glutamine and the glycine. Draw out the structure of a peptide with this sequence, including the appropriate stereochemistry for biological amino acids and assuming the peptide is at physiological pH (pH = 7.4). SGVTFQGKF b. What would the net charge of the peptide be at physiological pH? c. At what pH would the peptide be net neutral?

Chemistry for Today: General, Organic, and Biochemistry
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Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
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Chapter20: Enzymes
Section: Chapter Questions
Problem 20.50E
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4) Paxlovid is treatment for COVID-19 that was recently approved for use because it can
drastically reduce the risk for hospitalization and death when taken early in the
infection. It is actually a package of two different antiviral drugs. One of those is
Nirmatrelvir, which is a modified tripeptide protein mimetic designed to covalently bind
to and inhibit the main protease (MPro) from the SARS-CoV-2 virus. This protease
recognizes and hydrolyzes peptide bonds at specific points in their sequence, and it is
essential for viral replication.
a. Below is one of the sequences that Mpro recognizes and cleaves. It cleaves the peptide bond between
the glutamine and the glycine. Draw out the structure of a peptide with this sequence, including the
appropriate stereochemistry for biological amino acids and assuming the peptide is at physiological
pH (pH = 7.4).
SGVTFQGKF
b. What would the net charge of the peptide be at physiological pH?.
c. At what pH would the peptide be net neutral?
Transcribed Image Text:4) Paxlovid is treatment for COVID-19 that was recently approved for use because it can drastically reduce the risk for hospitalization and death when taken early in the infection. It is actually a package of two different antiviral drugs. One of those is Nirmatrelvir, which is a modified tripeptide protein mimetic designed to covalently bind to and inhibit the main protease (MPro) from the SARS-CoV-2 virus. This protease recognizes and hydrolyzes peptide bonds at specific points in their sequence, and it is essential for viral replication. a. Below is one of the sequences that Mpro recognizes and cleaves. It cleaves the peptide bond between the glutamine and the glycine. Draw out the structure of a peptide with this sequence, including the appropriate stereochemistry for biological amino acids and assuming the peptide is at physiological pH (pH = 7.4). SGVTFQGKF b. What would the net charge of the peptide be at physiological pH?. c. At what pH would the peptide be net neutral?
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