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Related Experiment Videos

Cyclopropane amino acid ester dipeptide sweeteners.

C Mapelli1, M G Newton, C E Ringold

  • 1Department of Chemistry, School of Chemical Sciences, University of Georgia, Athens.

International Journal of Peptide and Protein Research
|October 1, 1987
PubMed
Summary

Researchers synthesized novel L-aspartyl-1-aminocyclopropane carboxylic acid esters, discovering one variant 300 times sweeter than sucrose. This research explores potent artificial sweeteners and their chemical properties.

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Area of Science:

  • Organic Chemistry
  • Food Science
  • Biochemistry

Background:

  • Development of novel artificial sweeteners is crucial for managing sugar intake and related health issues.
  • Aspartame analogs are explored for enhanced sweetness and stability.
  • Understanding structure-activity relationships is key to designing effective sweet compounds.

Purpose of the Study:

  • To synthesize and evaluate the sweetness of various L-aspartyl-1-aminocyclopropane carboxylic acid esters.
  • To investigate the chemical stability of these dipeptide esters under different conditions.
  • To determine the molecular conformation of a representative ester through X-ray crystallography.

Main Methods:

  • Esterification of L-aspartyl-1-aminocyclopropane carboxylic acid with different alcohols.

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  • Sensory evaluation of the synthesized esters to determine their relative sweetness.
  • Chemical stability tests, including exposure to basic conditions.
  • X-ray diffraction analysis to elucidate the crystal structure and conformation of the propyl ester.

    • Main Results:

    • Several esters were successfully synthesized and their sweetness evaluated.
    • The sweetest ester demonstrated a sweetness approximately 300 times that of sucrose.
    • Basic conditions during synthesis led to undesired succinimide formation, even with protection.
    • The crystal structure of the propyl ester was determined, providing insights into its conformation.

    Conclusions:

    • Novel dipeptide esters of L-aspartyl-1-aminocyclopropane carboxylic acid can exhibit exceptionally high sweetness.
    • Chemical synthesis requires careful control of conditions to prevent side reactions like succinimide formation.
    • Structural analysis provides a basis for understanding the molecular features contributing to intense sweetness in these compounds.