Answers to all problems are at the end Î¿Î“this book. Detailed solutions are available in the Student Solutions Manual. Study Guide, and Problems Book. Characterizing a Covalent Enzyme Inhibitor Tosyl-L-phenylalanme cfaloromethyl ketone (TPCK) specifically inhibits chymotrypsin by covalently labeling His 57 Propose a mechanism for the inactivation reaction, indicating the structure of the produce(s). State why this inhibitor is specific tor cJiymotrypsin. Propose a reagent based on the structure of TPCK that might be an effective inhibitor of trypsin.

Question

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Answer 1

Textbook Question

Chapter 14, Problem 1P

Answers to all problems are at the end Î¿Î“this book. Detailed solutions are available in the Student Solutions Manual. Study Guide, and Problems Book.

Characterizing a Covalent Enzyme Inhibitor Tosyl-L-phenylalanme cfaloromethyl ketone (TPCK) specifically inhibits chymotrypsin by covalently labeling His⁵⁷

Chapter 14, Problem 1P, Answers to all problems are at the end Î¿Î“this book. Detailed solutions are available in the

Propose a mechanism for the inactivation reaction, indicating the structure of the produce(s).
State why this inhibitor is specific tor cJiymotrypsin.
Propose a reagent based on the structure of TPCK that might be an effective inhibitor of trypsin.

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

a.

Expert Solution

Interpretation Introduction

To propose: The mechanism for the inactivation reaction which indicates the structure of the products.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effect.

Explanation of Solution

Chymotrypsin undergoes covalent inactivation reaction by nucleophilic attack on the CH2 carbon of chloromethyl group of TPCK by the imidazole nitrogen of His57 results in the release of Cl as the released element.

So, the mechanism of inactivation reaction is given below:

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 1

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 2

Hence, from the above discussion, it is clear that chymotrypsin undergoes covalent inhibition reaction.

b.

Expert Solution

Interpretation Introduction

To propose: The reason for this inhibitor to be specific for chymotrypsin.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effects. Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The inhibitor is chymotrypsin specific because the chloromethyl keto group reaches the active site by the hydrophobic reactions of chymotrypsin and the phenyl group of TPCK.

Hence, from the above discussion, it is clear that the inhibitor is chymotrypsin specific.

c.

Expert Solution

Interpretation Introduction

To identify: A reagent that can be an effective inhibitor of Trypsin.

Introduction:

Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The phenylalanine residue of TPCK has to be replaced with lysine or arginine to produce the specific reagents for the enzyme Trypsin.

Hence, from the above discussion, it is clear that the residual portion of TPCK only produces the specific reagent for Trypsin.

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Answer 2

Textbook Question

Chapter 14, Problem 1P

Answers to all problems are at the end Î¿Î“this book. Detailed solutions are available in the Student Solutions Manual. Study Guide, and Problems Book.

Characterizing a Covalent Enzyme Inhibitor Tosyl-L-phenylalanme cfaloromethyl ketone (TPCK) specifically inhibits chymotrypsin by covalently labeling His⁵⁷

Chapter 14, Problem 1P, Answers to all problems are at the end Î¿Î“this book. Detailed solutions are available in the

Propose a mechanism for the inactivation reaction, indicating the structure of the produce(s).
State why this inhibitor is specific tor cJiymotrypsin.
Propose a reagent based on the structure of TPCK that might be an effective inhibitor of trypsin.

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

a.

Expert Solution

Interpretation Introduction

To propose: The mechanism for the inactivation reaction which indicates the structure of the products.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effect.

Explanation of Solution

Chymotrypsin undergoes covalent inactivation reaction by nucleophilic attack on the CH2 carbon of chloromethyl group of TPCK by the imidazole nitrogen of His57 results in the release of Cl as the released element.

So, the mechanism of inactivation reaction is given below:

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 1

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 2

Hence, from the above discussion, it is clear that chymotrypsin undergoes covalent inhibition reaction.

b.

Expert Solution

Interpretation Introduction

To propose: The reason for this inhibitor to be specific for chymotrypsin.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effects. Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The inhibitor is chymotrypsin specific because the chloromethyl keto group reaches the active site by the hydrophobic reactions of chymotrypsin and the phenyl group of TPCK.

Hence, from the above discussion, it is clear that the inhibitor is chymotrypsin specific.

c.

Expert Solution

Interpretation Introduction

To identify: A reagent that can be an effective inhibitor of Trypsin.

Introduction:

Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The phenylalanine residue of TPCK has to be replaced with lysine or arginine to produce the specific reagents for the enzyme Trypsin.

Hence, from the above discussion, it is clear that the residual portion of TPCK only produces the specific reagent for Trypsin.

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Answer 3

Textbook Question

Chapter 14, Problem 1P

Answers to all problems are at the end Î¿Î“this book. Detailed solutions are available in the Student Solutions Manual. Study Guide, and Problems Book.

Characterizing a Covalent Enzyme Inhibitor Tosyl-L-phenylalanme cfaloromethyl ketone (TPCK) specifically inhibits chymotrypsin by covalently labeling His⁵⁷

Chapter 14, Problem 1P, Answers to all problems are at the end Î¿Î“this book. Detailed solutions are available in the

Propose a mechanism for the inactivation reaction, indicating the structure of the produce(s).
State why this inhibitor is specific tor cJiymotrypsin.
Propose a reagent based on the structure of TPCK that might be an effective inhibitor of trypsin.

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

a.

Expert Solution

Interpretation Introduction

To propose: The mechanism for the inactivation reaction which indicates the structure of the products.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effect.

Explanation of Solution

Chymotrypsin undergoes covalent inactivation reaction by nucleophilic attack on the CH2 carbon of chloromethyl group of TPCK by the imidazole nitrogen of His57 results in the release of Cl as the released element.

So, the mechanism of inactivation reaction is given below:

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 1

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 2

Hence, from the above discussion, it is clear that chymotrypsin undergoes covalent inhibition reaction.

b.

Expert Solution

Interpretation Introduction

To propose: The reason for this inhibitor to be specific for chymotrypsin.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effects. Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The inhibitor is chymotrypsin specific because the chloromethyl keto group reaches the active site by the hydrophobic reactions of chymotrypsin and the phenyl group of TPCK.

Hence, from the above discussion, it is clear that the inhibitor is chymotrypsin specific.

c.

Expert Solution

Interpretation Introduction

To identify: A reagent that can be an effective inhibitor of Trypsin.

Introduction:

Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The phenylalanine residue of TPCK has to be replaced with lysine or arginine to produce the specific reagents for the enzyme Trypsin.

Hence, from the above discussion, it is clear that the residual portion of TPCK only produces the specific reagent for Trypsin.

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Textbook Question

Chapter 14, Problem 1P

Answers to all problems are at the end Î¿Î“this book. Detailed solutions are available in the Student Solutions Manual. Study Guide, and Problems Book.

Characterizing a Covalent Enzyme Inhibitor Tosyl-L-phenylalanme cfaloromethyl ketone (TPCK) specifically inhibits chymotrypsin by covalently labeling His⁵⁷

Chapter 14, Problem 1P, Answers to all problems are at the end Î¿Î“this book. Detailed solutions are available in the

Propose a mechanism for the inactivation reaction, indicating the structure of the produce(s).
State why this inhibitor is specific tor cJiymotrypsin.
Propose a reagent based on the structure of TPCK that might be an effective inhibitor of trypsin.

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

a.

Expert Solution

Interpretation Introduction

To propose: The mechanism for the inactivation reaction which indicates the structure of the products.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effect.

Explanation of Solution

Chymotrypsin undergoes covalent inactivation reaction by nucleophilic attack on the CH2 carbon of chloromethyl group of TPCK by the imidazole nitrogen of His57 results in the release of Cl as the released element.

So, the mechanism of inactivation reaction is given below:

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 1

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 2

Hence, from the above discussion, it is clear that chymotrypsin undergoes covalent inhibition reaction.

b.

Expert Solution

Interpretation Introduction

To propose: The reason for this inhibitor to be specific for chymotrypsin.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effects. Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The inhibitor is chymotrypsin specific because the chloromethyl keto group reaches the active site by the hydrophobic reactions of chymotrypsin and the phenyl group of TPCK.

Hence, from the above discussion, it is clear that the inhibitor is chymotrypsin specific.

c.

Expert Solution

Interpretation Introduction

To identify: A reagent that can be an effective inhibitor of Trypsin.

Introduction:

Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The phenylalanine residue of TPCK has to be replaced with lysine or arginine to produce the specific reagents for the enzyme Trypsin.

Hence, from the above discussion, it is clear that the residual portion of TPCK only produces the specific reagent for Trypsin.

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Textbook Question

Answer 6

Textbook Question

Answer 7

a.

Expert Solution

Interpretation Introduction

To propose: The mechanism for the inactivation reaction which indicates the structure of the products.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effect.

Explanation of Solution

Chymotrypsin undergoes covalent inactivation reaction by nucleophilic attack on the CH2 carbon of chloromethyl group of TPCK by the imidazole nitrogen of His57 results in the release of Cl as the released element.

So, the mechanism of inactivation reaction is given below:

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 1

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 2

Hence, from the above discussion, it is clear that chymotrypsin undergoes covalent inhibition reaction.

b.

Expert Solution

Interpretation Introduction

To propose: The reason for this inhibitor to be specific for chymotrypsin.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effects. Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The inhibitor is chymotrypsin specific because the chloromethyl keto group reaches the active site by the hydrophobic reactions of chymotrypsin and the phenyl group of TPCK.

Hence, from the above discussion, it is clear that the inhibitor is chymotrypsin specific.

c.

Expert Solution

Interpretation Introduction

To identify: A reagent that can be an effective inhibitor of Trypsin.

Introduction:

Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The phenylalanine residue of TPCK has to be replaced with lysine or arginine to produce the specific reagents for the enzyme Trypsin.

Hence, from the above discussion, it is clear that the residual portion of TPCK only produces the specific reagent for Trypsin.

Answer 8

a.

Expert Solution

Interpretation Introduction

To propose: The mechanism for the inactivation reaction which indicates the structure of the products.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effect.

Explanation of Solution

Chymotrypsin undergoes covalent inactivation reaction by nucleophilic attack on the CH2 carbon of chloromethyl group of TPCK by the imidazole nitrogen of His57 results in the release of Cl as the released element.

So, the mechanism of inactivation reaction is given below:

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 1

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 2

Hence, from the above discussion, it is clear that chymotrypsin undergoes covalent inhibition reaction.

Answer 9

a.

Expert Solution

Answer 10

a.

Expert Solution

Answer 11

Expert Solution

Answer 12

Interpretation Introduction

To propose: The mechanism for the inactivation reaction which indicates the structure of the products.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effect.

Answer 13

Explanation of Solution

Chymotrypsin undergoes covalent inactivation reaction by nucleophilic attack on the CH2 carbon of chloromethyl group of TPCK by the imidazole nitrogen of His57 results in the release of Cl as the released element.

So, the mechanism of inactivation reaction is given below:

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 1

BIOCHEMISTRY II >CUSTOM<, Chapter 14, Problem 1P , additional homework tip 2

Hence, from the above discussion, it is clear that chymotrypsin undergoes covalent inhibition reaction.

Answer 14

b.

Expert Solution

Interpretation Introduction

To propose: The reason for this inhibitor to be specific for chymotrypsin.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effects. Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The inhibitor is chymotrypsin specific because the chloromethyl keto group reaches the active site by the hydrophobic reactions of chymotrypsin and the phenyl group of TPCK.

Hence, from the above discussion, it is clear that the inhibitor is chymotrypsin specific.

Answer 15

b.

Expert Solution

Answer 16

b.

Expert Solution

Answer 17

Expert Solution

Answer 18

Interpretation Introduction

To propose: The reason for this inhibitor to be specific for chymotrypsin.

Introduction:

Covalent enzyme inhibitor like TPCK is slowly reversible or totally irreversible. In many cases, these inhibitors are used to validate the pathway or target. There are targeted covalent enzyme inhibitors that have a slow offset, high binding efficiency as well as high potency to bind, increased selectivity decreased propensity for target-based drug resistance and prolonged pharmacodynamic effects. Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Answer 19

Explanation of Solution

The inhibitor is chymotrypsin specific because the chloromethyl keto group reaches the active site by the hydrophobic reactions of chymotrypsin and the phenyl group of TPCK.

Hence, from the above discussion, it is clear that the inhibitor is chymotrypsin specific.

Answer 20

c.

Expert Solution

Interpretation Introduction

To identify: A reagent that can be an effective inhibitor of Trypsin.

Introduction:

Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Explanation of Solution

The phenylalanine residue of TPCK has to be replaced with lysine or arginine to produce the specific reagents for the enzyme Trypsin.

Hence, from the above discussion, it is clear that the residual portion of TPCK only produces the specific reagent for Trypsin.

Answer 21

c.

Expert Solution

Answer 22

c.

Expert Solution

Answer 23

Expert Solution

Answer 24

Interpretation Introduction

To identify: A reagent that can be an effective inhibitor of Trypsin.

Introduction:

Chymotrypsin plays an important part in the breakdown of proteins which is called proteolysis. The pancreas synthesizes the chymotrypsin. It cleaves the peptide amino bonds to digest the proteins.

Answer 25

Explanation of Solution

The phenylalanine residue of TPCK has to be replaced with lysine or arginine to produce the specific reagents for the enzyme Trypsin.

Hence, from the above discussion, it is clear that the residual portion of TPCK only produces the specific reagent for Trypsin.

Answer 26

Ch. 14 - Answers to all problems are at the end Î¿Î“this...Ch. 14 - Answers to all problems are at the end Î¿Î“this...Ch. 14 - Prob. 3P Ch. 14 - Prob. 4P Ch. 14 - Answers to all problems are at the end Î¿Î“this...Ch. 14 - Prob. 6P Ch. 14 - Prob. 7P Ch. 14 - Answers to all problems are at the end Î¿Î“this...Ch. 14 - Answers to all problems are at the end Î¿f this...Ch. 14 - Answers to all problems are at the end Î¿f this...

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