Mechanisms for the three steps involved in the conversion of 3-phosphoglycerate into glyceraldehyde-3-phosphate, 1) Phosphorylation of 3-phosphoglycerate by treating with ATP to form 1,3- bisphosphoglycerate.2) Reaction of 1,3- bisphosphoglycerate with the thiol group on the enzyme to give an enzyme-bound thioester 3) Reduction of the enzyme bound thioester with NADH, are to be proposed. Concept introduction: All the three steps involved in the conversion of 3-phosphoglycerate into glyceraldehyde-3-phosphate take place through two steps i) Attack of a nucleophile on either P or C and ii) Elimination of the leaving group. To propose: Mechanisms for the three steps involved in the conversion of 3-phosphoglycerate into glyceraldehyde-3-phosphate 1) Phosphorylation of 3-phosphoglycerate by treating with ATP to form 1,3- bisphosphoglycerate 2) Reaction of 1,3- bisphosphoglycerate with the thiol group on the enzyme to give an enzyme-bound thioester 3) Reduction of the enzyme bound thioester with NADH.

Question

Synthesis of Ibuprofen-Part 2: 1. Some pain relievers including ibuprofen (MotrinⓇ) and naproxen (Aleve®) are "α-arylpropanoic acids." Look up the structure of naproxen (AleveⓇ), another a-arylpropionic acid. Using the same reactions that we used for making ibuprofen, show how to make naproxen from the compound below. Show all intermediates and reagents in your synthesis. Show how you would prepare ibuprofen starting from p-isobutylbenzene rather than p-isobutylacetophenenone. What reaction steps would need to change/add? 3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?

Answer 1

Question

Chapter 21.SE, Problem 41MP

Interpretation Introduction

Interpretation:

Mechanisms for the three steps involved in the conversion of 3-phosphoglycerate into glyceraldehyde-3-phosphate, 1) Phosphorylation of 3-phosphoglycerate by treating with ATP to form 1,3- bisphosphoglycerate.2) Reaction of 1,3- bisphosphoglycerate with the thiol group on the enzyme to give an enzyme-bound thioester 3) Reduction of the enzyme bound thioester with NADH, are to be proposed.

Concept introduction:

All the three steps involved in the conversion of 3-phosphoglycerate into glyceraldehyde-3-phosphate take place through two steps i) Attack of a nucleophile on either P or C and ii) Elimination of the leaving group.

To propose:

Mechanisms for the three steps involved in the conversion of 3-phosphoglycerate into glyceraldehyde-3-phosphate 1) Phosphorylation of 3-phosphoglycerate by treating with ATP to form 1,3- bisphosphoglycerate 2) Reaction of 1,3- bisphosphoglycerate with the thiol group on the enzyme to give an enzyme-bound thioester 3) Reduction of the enzyme bound thioester with NADH.

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Synthesis of Ibuprofen-Part 2: 1. Some pain relievers including ibuprofen (MotrinⓇ) and naproxen (Aleve®) are "α-arylpropanoic acids." Look up the structure of naproxen (AleveⓇ), another a-arylpropionic acid. Using the same reactions that we used for making ibuprofen, show how to make naproxen from the compound below. Show all intermediates and reagents in your synthesis. Show how you would prepare ibuprofen starting from p-isobutylbenzene rather than p-isobutylacetophenenone. What reaction steps would need to change/add? 3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?

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