Change the stereochemistry of the three pre-drawn bond line formulas of aspartame to generate the three bitter stereoisomers of aspartame. OH * Edit Drawing

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
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Aspartame is an artificial sweetener sold under the trade name NutraSweetTM. Aspartame is the methyl ester of a dipeptide
formed from L-aspartic acid and L-phenylalanine and can be summarized as Asp-Phe-OCH3. Surprisingly, the analogous ethyl ester
(Asp-Phe-OCH,CH3) is not sweet. If either L residue is replaced with its enantiomeric D residue, the resulting compound is bitter
instead of sweet.
25.028a
Your answer is correct.
Draw a bond-line structure of aspartame. Do NOT explicitly draw any hydrogen atoms in your structure or use abbreviations
like OMe, COOH or Ph.
CH3
NH2
Transcribed Image Text:Aspartame is an artificial sweetener sold under the trade name NutraSweetTM. Aspartame is the methyl ester of a dipeptide formed from L-aspartic acid and L-phenylalanine and can be summarized as Asp-Phe-OCH3. Surprisingly, the analogous ethyl ester (Asp-Phe-OCH,CH3) is not sweet. If either L residue is replaced with its enantiomeric D residue, the resulting compound is bitter instead of sweet. 25.028a Your answer is correct. Draw a bond-line structure of aspartame. Do NOT explicitly draw any hydrogen atoms in your structure or use abbreviations like OMe, COOH or Ph. CH3 NH2
Change the stereochemistry of the three pre-drawn bond line formulas of aspartame to generate the three bitter
stereoisomers of aspartame.
CH,
CH
CH2
H.N
H,N
H,N
Edit Drawing
Transcribed Image Text:Change the stereochemistry of the three pre-drawn bond line formulas of aspartame to generate the three bitter stereoisomers of aspartame. CH, CH CH2 H.N H,N H,N Edit Drawing
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