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ISSN 0582-9879 Acta Biochim et Biophysica Sinica 2004, 36(6):385-389 CN
31-1300/Q
Synthesis and Characteristics of an Aspartame Analogue, L-Asparaginyl
L-3-Phenyllactic Acid Methyl Ester
Hu TAO1, Da-Fu CUI1, and You-Shang ZHANG1,2*
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