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Aspartame, the artificial sweetener marketed under the name NutraSweet, is a methyl ester of a dipeptide. The structure of aspartame is (EQUATION CAN'T COPY)a. What two amino acids are used to prepare aspartame?b. There is concern that methanol may be produced by the decomposition of aspartame. From what portion of the molecule can methanol be produced? Write an equation for this reaction.
a. aspartic acid and phenyl-alanine; b. Aspartame contains the methyl ester of phenylalanine. This ester can hydrolyze to form methanol, $\mathrm{R}-\mathrm{CO}_{2} \mathrm{CH}_{3}+$ $\mathrm{H}_{2} \mathrm{O} \rightleftharpoons \mathrm{RCO}_{2} \mathrm{H}+\mathrm{CH}_{3} \mathrm{OH}$
Organic Chemistry
Chapter 21
Organic and Biochemical Molecules
Organic compounds
Carbohydrates, proteins, and lipids
Amino Acids, Peptides, and Proteins
University of North Texas
Rice University
Lectures
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in this question. We're looking at the structure of s pertain. And the first question or the first part asks us to identify the two amino acids used to make ascertain. So there is one right here. Um, this is the carb oxalic acid group. Is this a central carbon on? And this is the amad bond to the next amino acid on this is our group down here and so that our group is a Spartak acid, uh, see shoe, and then a core box cilic acid. And then the second amino acid is the rest of the structure there. Um and so this one is fennel Allan E. And we can tell that because this is our central apartment now it's connected to the amine. Um and this is our our group, so see, issue and the benzene ring is final. Allan E um, And then the part B says that there is some concern that methanol can be formed from this, um structure and were asked, identify what part of the molecule that would come from and then write a reaction for that. So this piece of here, um, if we were to draw it out better would look like this. And so this is a method all portion that we would be worried about. So that is where on the molecule. Right here. We're worried about getting methanol from and the reaction, But I would be with water reacting with that, Esther. So it would be, um, the Esther reacting with water. Teoh form a car box. Look. Acid and methanol. So that is the reaction for a party.
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