Acid Hydrolysis of Aspartame and Identification of its Products by Thin Layer Chromatography

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 14 Issue 6 (2009) pp 243-246

Acid Hydrolysis of Aspartame and Identification of its Products by Thin Layer Chromatography

Amanda Melberg, Paige Adejare, and William H. Flurkey*

Department of Chemistry, Indiana State University, Terre Haute, IN 47809, wflurkeyiii@isugw.indstate.edu
Received January 26, 2009. Accepted July 1, 2009.

Published online: 31 December 2009

Abstract. Aspartame, a sugar substitute, is a modified peptide composed of aspartic acid and phenylalanine methyl ester. Hydrolysis of aspartame can produce a variety of products, including α-L-aspartyl-L-phenylalanine, L-phenylalanyl-α-L-aspartic acid, L-aspartic acid, L-phenylalanine, and L-phenylalanine methyl ester. Many of these products can be identified using thin layer chromatography. The products from acid hydrolysis of aspartame were followed over a six-hour period using thin layer chromatography. Conversion of aspartame into the peptide aspartyl phenylalanine was observed, followed by conversion of the peptide into aspartic acid and phenylalanine. No conversion of aspartame into phenylalanine methyl ester or a β isomer of aspartyl phenylalanine was observed. This experiment uses common techniques to demonstrate hydrolysis of a peptide and to identify the products obtained from acid hydrolysis of a peptide.

Key Words: In the Classroom; organic chemistry

(*) Corresponding author. (E-mail: wflurkeyiii@isugw.indstate.edu)

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