Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 23, Problem 23.65SP
Retroviruses like HIV, the pathogen responsible for AIDS, incorporate an RNA template that is copied into DNA during infection. The reverse transcriptase enzyme that copies RNA into DNA is relatively nonselective and error-prone, leading to a high mutation rate. Its lack of selectivity is exploited by the anti-HIV drug AZT (3′ — azido – 23′ – dideoxythymidine), which becomes phosphorylated and is incorporated by reverse transcriptase into DNA where it acts as a chain terminator. Mammalian DNA polymerases are more selective, having a low affinity for AZT, so its toxicity is relatively low.
- a. Draw the structures of AZT and natural deoxythymidine.
- b. Draw the structure of AZT 5′ – triphosphate, the derivative that inhibits reverse transcriptase.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Retroviruses like HIV, the pathogen responsible for AIDS, incorporate an RNA template that is copied into DNA duringinfection. The reverse transcriptase enzyme that copies RNA into DNA is relatively nonselective and error-prone, leadingto a high mutation rate. Its lack of selectivity is exploited by the anti-HIV drug AZT (3′@azido@2′,3′@dideoxythymidine),which becomes phosphorylated and is incorporated by reverse transcriptase into DNA, where it acts as a chain terminator.Mammalian DNA polymerases are more selective, having a low affinity for AZT, so its toxicity is relatively low.(a) Draw the structures of AZT and natural deoxythymidine.(b) Draw the structure of AZT 5′@triphosphate, the derivative that inhibits reverse transcriptase.*2
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?
Many peptides react further after synthesis
(process is called post-translational modification).
In this example a cysteine cyclizes to form a thiazole
ring in Sanguinamide A.
O=
HN
HN"
SH
-H₂O
o=
HN"
0=
0=
N₂ S
HN
Sanguinamide A
Chapter 23 Solutions
Organic Chemistry (9th Edition)
Ch. 23.2 - Prob. 23.1PCh. 23.3A - Prob. 23.2PCh. 23.3A - Prob. 23.3PCh. 23.3B - Draw and name the enantiomers of the sugars shown...Ch. 23.3B - Prob. 23.5PCh. 23.3C - Prob. 23.6PCh. 23.4 - Draw the Haworth projection for the cyclic...Ch. 23.4 - Prob. 23.8PCh. 23.4 - Prob. 23.9PCh. 23.4 - Prob. 23.10P
Ch. 23.4 - Prob. 23.11PCh. 23.5 - Prob. 23.12PCh. 23.5 - Prob. 23.13PCh. 23.6 - Prob. 23.14PCh. 23.6 - Prob. 23.15PCh. 23.7 - Prob. 23.16PCh. 23.7 - Prob. 23.17PCh. 23.7 - Two sugars, A and B, are known to be glucose and...Ch. 23.7 - Prob. 23.19PCh. 23.8 - Prob. 23.20PCh. 23.8 - Prob. 23.21PCh. 23.8 - Prob. 23.22PCh. 23.8 - Prob. 23.23PCh. 23.8 - Prob. 23.24PCh. 23.9 - a. Show the product that results when fructose is...Ch. 23.9 - Prob. 23.26PCh. 23.9 - Prob. 23.27PCh. 23.9 - Prob. 23.28PCh. 23.10 - Prob. 23.29PCh. 23.10 - Prob. 23.30PCh. 23.10 - Prob. 23.31PCh. 23.11 - Prob. 23.32PCh. 23.11 - The Wohl degradation, an alternative to the Ruff...Ch. 23.11 - Prob. 23.34PCh. 23.11 - Prob. 23.35PCh. 23.12A - Prob. 23.36PCh. 23.12A - Give an equation to show the reduction of Tollens...Ch. 23.12A - Prob. 23.38PCh. 23.12B - Prob. 23.39PCh. 23.12C - Prob. 23.40PCh. 23.12C - Prob. 23.41PCh. 23.13A - Prob. 23.42PCh. 23.15 - Cytosine, uracil, and guanine have tautomeric...Ch. 23.15 - a. An aliphatic aminoglycoside is relatively...Ch. 23.16C - Prob. 23.45PCh. 23 - Prob. 23.46SPCh. 23 - Prob. 23.47SPCh. 23 - Prob. 23.48SPCh. 23 - Prob. 23.49SPCh. 23 - Prob. 23.50SPCh. 23 - Prob. 23.51SPCh. 23 - Prob. 23.52SPCh. 23 - Prob. 23.53SPCh. 23 - Prob. 23.54SPCh. 23 - Prob. 23.55SPCh. 23 - Prob. 23.56SPCh. 23 - Prob. 23.57SPCh. 23 - Prob. 23.58SPCh. 23 - Prob. 23.59SPCh. 23 - Prob. 23.60SPCh. 23 - Prob. 23.61SPCh. 23 - Prob. 23.62SPCh. 23 - Prob. 23.63SPCh. 23 - Draw the structure of a four-residue segment of...Ch. 23 - Retroviruses like HIV, the pathogen responsible...Ch. 23 - Prob. 23.66SPCh. 23 - Prob. 23.67SP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- The following data were recorded from an experiment to measure the activity of a peptidase enzyme. A number of solutions of different concentrations of a dipeptide were prepared then the same small amount of the enzyme was added to each of them. The rate of cleavage of the peptide bond was measured and the initial rate of the reaction was recorded Peptide conc (mmol L-¹) 0.334 0.450 0.667 1.00 1.33 1.67 Initial rate 0.152 0.201 0.269 0.417 0.505 0.667 (mmol L¹ s¹) For the peptidase enzyme find the maximum velocity and the Michaelis constant.arrow_forwardQ23: Dr. Alghe has just performed a restriction digest on DNA she extracted from her samples. She must now run her DNA out on a gel to separate the fragments based on size. To do this she must prepare a 1.1% agarose gel, where the percentage is determined as mass/vol. How many grams of agarose must she add to 413 mL of buffer in order to arrive at the correct percentage? (answer to 2 decimals) **Assume the dissolution of agarose will not alter the final volume of the solution**arrow_forwardDuring base excision repair, DNA glycosylase cleaves theN-glycosidic link between the altered base and the deoxyribose component of the nucleotide. Draw a typical nucleotideand indicate which bond is cleaved.arrow_forward
- Suppose that 28% of the nucleotides in a DNA molecule are deoxythymidine 5'-monophosphate, and that during DNA replication the percentage amounts of available nucleotide bases art 22% A, 22% C, 28% G. and 28% T. Which base would be depleted first in the replication process?arrow_forward22-61 Polyglutamic acid (a polypeptide chain made only of glutamic acid residues) has an a-helix conformation below pH 6.0 and a random-coil conformation above pH 6.0. What is the reason for this conformational change?arrow_forwardDraw the complete structure of the ribonucleotide codon UAC. For what amino acid does this sequence code?arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningGeneral, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage LearningOrganic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,
- Chemistry & Chemical ReactivityChemistryISBN:9781337399074Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning
Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781337399074
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Nucleic acids - DNA and RNA structure; Author: MEDSimplified;https://www.youtube.com/watch?v=0lZRAShqft0;License: Standard YouTube License, CC-BY