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) 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 (MPr°) 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). %3D SGVTFQGKF b. What would the net charge of the peptide be at physiological pH? c. At what pH would the peptide be net neutral?

) 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 (MPr°) 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). %3D SGVTFQGKF b. What would the net charge of the peptide be at physiological pH? c. At what pH would the peptide be net neutral?

Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter23: Enzymes
Section: Chapter Questions
Problem 23.25P: 5 Which of the following is a correct statement describing the induced-fit model of enzyme action?...
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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?
d. Below are the final two steps of Pfizer's chemical synthesis of Nirmaltrelvir. Because it is a protease inhibitor, it mimics the structure of a peptide with a similar amide backbone. Thus, to synthesize it, the scientists at Pfizer used an EDC coupling in the penultimate step. он NH EDC NH NH2 NH2 Step 1 NH NH Step 2 „NH Nirmatrelvir Draw a detailed arrow-pushing mechanism for Step 1 as labeled in the image above. You can assume that the reaction takes place in aqueous conditions at a pH of 4-6. Feel free to use clearly defined R groups to abbreviate the molecules.
Transcribed Image Text:d. Below are the final two steps of Pfizer's chemical synthesis of Nirmaltrelvir. Because it is a protease inhibitor, it mimics the structure of a peptide with a similar amide backbone. Thus, to synthesize it, the scientists at Pfizer used an EDC coupling in the penultimate step. он NH EDC NH NH2 NH2 Step 1 NH NH Step 2 „NH Nirmatrelvir Draw a detailed arrow-pushing mechanism for Step 1 as labeled in the image above. You can assume that the reaction takes place in aqueous conditions at a pH of 4-6. Feel free to use clearly defined R groups to abbreviate the molecules.
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