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Acetylcholine is a neurotransmitter that sends electrical impulses across junctions between nerve cells, and from motor neurons to muscle cells, causing muscle cells to contract. As part of a normal deactivation mechanism, acetylcholine is hydrolysed in the body by the enzyme acetylcholine esterase to give choline and acetic acid, as shown below. acetylcholine esterase buk HO acetylcholine Lov OH Acetylcholinesterase is a serine hydrolase with the catalytic triad of serine-200 (R= -CH₂OHI). glutamic acid-327 (R = -CH:CO:H) and histidine-440 (see below) groups in its active site. R CH₂ Histidine side chain group i) Suggest the likely binding interactions that would occur at physiological pH between acetylcholine and acetylcholinesterase in the enzyme active site. You will need to draw the active site of acetylcholinesterase and acetylcholine and use lone pairs of electrons and 8* and 8. ii) With reference to the structures of acetylcholine (above) and physostigmine (below) suggest how physostigmine can act as a reversible covalent competitive inhibitor of acetylcholinesterase. Also briefly explain why physostigmine is used for the treatment of myasthenia gravis (a disease characterised by chronic muscle weakness). thas physostigmine iii) Bethanechol is an acetylcholine agonist that can be used to reverse the action of acetylcholine-based muscle relaxants after surgery. Show how bethanechol can act as an acetylcholine agonist AND also provide an explanation for why it is orally and intravenously more stable than acetylcholine. Hand Lone H₂N bethanechol

Acetylcholine is a neurotransmitter that sends electrical impulses across junctions between nerve cells, and from motor neurons to muscle cells, causing muscle cells to contract. As part of a normal deactivation mechanism, acetylcholine is hydrolysed in the body by the enzyme acetylcholine esterase to give choline and acetic acid, as shown below. acetylcholine esterase buk HO acetylcholine Lov OH Acetylcholinesterase is a serine hydrolase with the catalytic triad of serine-200 (R= -CH₂OHI). glutamic acid-327 (R = -CH:CO:H) and histidine-440 (see below) groups in its active site. R CH₂ Histidine side chain group i) Suggest the likely binding interactions that would occur at physiological pH between acetylcholine and acetylcholinesterase in the enzyme active site. You will need to draw the active site of acetylcholinesterase and acetylcholine and use lone pairs of electrons and 8* and 8. ii) With reference to the structures of acetylcholine (above) and physostigmine (below) suggest how physostigmine can act as a reversible covalent competitive inhibitor of acetylcholinesterase. Also briefly explain why physostigmine is used for the treatment of myasthenia gravis (a disease characterised by chronic muscle weakness). thas physostigmine iii) Bethanechol is an acetylcholine agonist that can be used to reverse the action of acetylcholine-based muscle relaxants after surgery. Show how bethanechol can act as an acetylcholine agonist AND also provide an explanation for why it is orally and intravenously more stable than acetylcholine. Hand Lone H₂N bethanechol

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Acetylcholine is a neurotransmitter that sends electrical impulses across junctions between nerve cells, and from motor neurons to muscle cells, causing muscle cells to contract. As part of a normal deactivation mechanism, acetylcholine is hydrolysed in the body by the enzyme acetylcholine esterase to give choline and acetic acid, as shown below. acetylcholine esterase вик HO acetylcholine ion OH Acetylcholinesterase is a serine hydrolase with the catalytic triad of serine-200 (R= -CH₂OH). glutamic acid-327 (R = -CH:CO:H) and histidine-440 (see below) groups in its active site. R=CH₂ Histidine side chain group i) Suggest the likely binding interactions that would occur at physiological pH between acetylcholine and acetylcholinesterase in the enzyme active site. You will need to draw the active site of acetylcholinesterase and acetylcholine and use lone pairs of electrons and 8 and 8. ii) With reference to the structures of acetylcholine (above) and physostigmine (below) suggest how physostigmine can act as a reversible covalent competitive inhibitor of acetylcholinesterase. Also briefly explain why physostigmine is used for the treatment of myasthenia gravis (a disease characterised by chronic muscle weakness). physostigmine iii) Bethanechol is an acetylcholine agonist that can be used to reverse the action of acetylcholine-based muscle relaxants after surgery. Show how bethanechol can act as an acetylcholine agonist AND also provide an explanation for why it is orally and intravenously more stable than acetylcholine. HENI LONK H₂N bethanechol
Transcribed Image Text:Acetylcholine is a neurotransmitter that sends electrical impulses across junctions between nerve cells, and from motor neurons to muscle cells, causing muscle cells to contract. As part of a normal deactivation mechanism, acetylcholine is hydrolysed in the body by the enzyme acetylcholine esterase to give choline and acetic acid, as shown below. acetylcholine esterase вик HO acetylcholine ion OH Acetylcholinesterase is a serine hydrolase with the catalytic triad of serine-200 (R= -CH₂OH). glutamic acid-327 (R = -CH:CO:H) and histidine-440 (see below) groups in its active site. R=CH₂ Histidine side chain group i) Suggest the likely binding interactions that would occur at physiological pH between acetylcholine and acetylcholinesterase in the enzyme active site. You will need to draw the active site of acetylcholinesterase and acetylcholine and use lone pairs of electrons and 8 and 8. ii) With reference to the structures of acetylcholine (above) and physostigmine (below) suggest how physostigmine can act as a reversible covalent competitive inhibitor of acetylcholinesterase. Also briefly explain why physostigmine is used for the treatment of myasthenia gravis (a disease characterised by chronic muscle weakness). physostigmine iii) Bethanechol is an acetylcholine agonist that can be used to reverse the action of acetylcholine-based muscle relaxants after surgery. Show how bethanechol can act as an acetylcholine agonist AND also provide an explanation for why it is orally and intravenously more stable than acetylcholine. HENI LONK H₂N bethanechol
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