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ISSN 0582-9879 Acta Biochim et Biophysica Sinica 2004, 36(6):385-389 CN 31-1300/Q

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Synthesis and Characteristics of an Aspartame Analogue, L-Asparaginyl L-3-Phenyllactic Acid Methyl Ester

Hu TAO¹, Da-Fu CUI¹, and You-Shang ZHANG^1,2*

¹Institute of Biochemistry and Cell Biology, Shanghai Institutes for Biological Sciences, the Chinese Academy of Sciences, Shanghai 200031, China;
²Institute of Protein Research, Tongji University, Shanghai 200031, China

Abstract An aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester was synthesized with aspartic acid replaced by asparagine and peptide bond replaced by ester bond. The aspartic acid of aspartame could be replaced by asparagine as reported in the literature. In this analogue, the hydrogen of amide group could still form a hydrogen bond with the oxygen of ester bond and the ester bond was isosteric with peptide bond. However, the product was not sweet, showing that the peptide bond could not be replaced by ester bond. The peptide C-N bond behaves as a double bond that is not free to rotate and the C, O, N and H atoms are in the same plane. The replacement of peptide bond by ester bond destroyed the unique conformation of peptide bond, resulting in the loss of sweet taste.

Key words artificial sweetener; aspartame derivative; peptide bond

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Received: March 8, 2004 Accepted: May 12, 2004

*Corresponding author: Tel, 86-21-54921237; Fax: 86-21-54921011; E-mail, [email protected]

Date 2004-6-11 CORRECTION

The first affiliation ¹Institute of Biochemistry and Cell Biology, Shanghai Institutes for Biological Sciences, the Chinese Academy of Sciences, Shanghai 200031, China

Should be changed to: ¹Institute of Biochemistry and Cell Biology, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Graduate School of the Chinese Academy of Sciences, Shanghai 200031, China