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10. Answer ALL parts of this question. (a) Capravirine is a third-generation non-nucleoside reverse transcriptase inhibitor (NNRTI) with a side chain that takes part in important hydrogen bonding to Lys-103 and Pro-236 in the allosteric binding site, yet the side chain has a carbonyl group. Discuss whether this makes the structure prone to enzymatic hydrolysis and inactivation. Use curly arrows to show the role played by any stabilising group. HIN Lys-103 N-H- Capravirine Lys-101 Pro-236 (15 marks) (b) Most Pls bind to the active site with a water molecule acting as a hydrogen bonding bridge to the enzyme flaps. Suggest what relevance this information might have in the design of novel Pls. (5 marks)

10. Answer ALL parts of this question. (a) Capravirine is a third-generation non-nucleoside reverse transcriptase inhibitor (NNRTI) with a side chain that takes part in important hydrogen bonding to Lys-103 and Pro-236 in the allosteric binding site, yet the side chain has a carbonyl group. Discuss whether this makes the structure prone to enzymatic hydrolysis and inactivation. Use curly arrows to show the role played by any stabilising group. HIN Lys-103 N-H- Capravirine Lys-101 Pro-236 (15 marks) (b) Most Pls bind to the active site with a water molecule acting as a hydrogen bonding bridge to the enzyme flaps. Suggest what relevance this information might have in the design of novel Pls. (5 marks)

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter27: Amino Acids And Proteins
Section: Chapter Questions
Problem 27.45P
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10. Answer ALL parts of this question. (a) Capravirine is a third-generation non-nucleoside reverse transcriptase inhibitor (NNRTI) with a side chain that takes part in important hydrogen bonding to Lys-103 and Pro-236 in the allosteric binding site, yet the side chain has a carbonyl group. Discuss whether this makes the structure prone to enzymatic hydrolysis and inactivation. Use curly arrows to show the role played by any stabilising group. HIN Lys-103 N-H- Capravirine Lys-101 Pro-236 (15 marks) (b) Most Pls bind to the active site with a water molecule acting as a hydrogen bonding bridge to the enzyme flaps. Suggest what relevance this information might have in the design of novel Pls. (5 marks)
Transcribed Image Text:10. Answer ALL parts of this question. (a) Capravirine is a third-generation non-nucleoside reverse transcriptase inhibitor (NNRTI) with a side chain that takes part in important hydrogen bonding to Lys-103 and Pro-236 in the allosteric binding site, yet the side chain has a carbonyl group. Discuss whether this makes the structure prone to enzymatic hydrolysis and inactivation. Use curly arrows to show the role played by any stabilising group. HIN Lys-103 N-H- Capravirine Lys-101 Pro-236 (15 marks) (b) Most Pls bind to the active site with a water molecule acting as a hydrogen bonding bridge to the enzyme flaps. Suggest what relevance this information might have in the design of novel Pls. (5 marks)
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