Glutathione is a coenzyme consisting of the tripeptide Glu-Cys-Gly. The first step of the synthesis of glutathione is catalyzed by glutamyl cysteine synthetase, where glutamate reacts with ATP to form an acyl phosphate. In the second step, cysteine reacts with the acyl phosphate to form F1F1F1S1F1F1F10-Glu-Cys and phosphate ion. Note, the F1F1F1S1F1F1F10-Glu indicates the reaction occurs on the sidechain. Draw the acyl phosphate formed in the first step, and then draw a plausible curved-arrow mechanism showing how the acyl phosphate can be converted to F1F1F1S1F1F1F10-Glu-Cys.

In the first step, ATP reacts with the c

Exam 25: The Chemistry of Thioesters, Phosphate Esters, and Phosphate Anhydrides

Draw a plausible curved-arrow mechanism to show the base-catalyzed hydrolysis of the phosphate triester, then draw the hydrolysis products.

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Question 21

Predict the major organic product(s) for the reaction. If the reaction will not occur, write NR and explain why.

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Question 22

Glutathione is a coenzyme consisting of the tripeptide Glu-Cys-Gly. The first step of the synthesis of glutathione is catalyzed by glutamyl cysteine synthetase, where glutamate reacts with ATP to form an acyl phosphate. In the second step, cysteine reacts with the acyl phosphate to form -Glu-Cys and phosphate ion. Note, the -Glu indicates the reaction occurs on the sidechain. Draw the acyl phosphate formed in the first step, and then draw a plausible curved-arrow mechanism showing how the acyl phosphate can be converted to -Glu-Cys.

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Question 23

Give two reasons why ATP is a high energy compound.

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Question 24

Calculate the ΔG°´ for the phosphorylation of fructose-6-phosphate to fructose 1,6-biphosphate using ATP, given the following.

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Question 25

Showing 21 - 25 of 25

Draw a plausible curved-arrow mechanism to show the base-catalyzed hydrolysis of the phosphate triester, then draw the hydrolysis products.

Predict the major organic product(s) for the reaction. If the reaction will not occur, write NR and explain why.

Give two reasons why ATP is a high energy compound.

Calculate the ΔG°´ for the phosphorylation of fructose-6-phosphate to fructose 1,6-biphosphate using ATP, given the following.

Chemical Bonding and Chemical Structure

Alkanes and Organic Nomenclature

The Curved-Arrow Notation, Resonance, Acids and Bases, and Chemical Equilibrium

Introduction to Alkenes and Alkynes

Addition Reactions of Alkenes and Alkynes

Principles of Stereochemistry

Cyclic Compounds and Reaction Stereochemistry

Nomenclature and Noncovalent Intermolecular Interactions

The Chemistry of Alkyl Halides

Free-Radical Reactions, Main-Group Organometallic Compounds, and Carbenes

The Chemistry of Alcohols and Thiols

The Chemistry of Ethers, Epoxides, Glycols, and Sulfides

Introduction to Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Dienes and Aromaticity

The Chemistry of Benzene and Its Derivatives

Allylic and Benzylic Reactivity

The Chemistry of Aryl Halides, Vinylic Halides, and Phenols

The Chemistry of Aldehydes and Ketones

The Chemistry of Carboxylic Acids

The Chemistry of Carboxylic Acid Derivatives

The Chemistry of Enolate Ions, Enols, and Α,β-Unsaturated Carbonyl Compounds

The Chemistry of Amines

Carbohydrates

The Chemistry of the Aromatic Heterocycles and Nucleic Acids

Amino Acids, Peptides, and Proteins

Pericyclic Reactions

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