Aspartame is an artificial sweetener sold under the trade name NutraSweet TM . Aspartame is the methyl

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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-OCH2CH3) is not sweet. If either l residue is replaced with its enantiomeric d residue, the resulting compound is bitter instead of sweet.

(a) Draw a bond-line structure of aspartame.

(b) Draw a bond-line structure for each of the three bitter stereoisomers of aspartame.

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Organic Chemistry

ISBN: 978-0470917800

1st edition

Authors: David R. Klein

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