Synthesis and Optimization of Ergothioneine Derivatives

Ballerini, Anita

Synthesis and Optimization of Ergothioneine Derivatives

Thesis / Dissertation

2026

Publisher

University of Cape Town

Department

Department of Chemistry

Faculty

Faculty of Science

Abstract

Ergothioneine (EGT, Figure a) is a naturally occurring sulfur-containing amino acid derived from histidine, known for its antioxidant properties in living organisms and its significant potential in the pharmaceutical and cosmetic industry. The objective of this study is to establish an effective protocol for the synthesis and purification of EGT derivatives that could lead to high purity sustainably produced product. A key challenge was balancing reaction efficiency with selective thiolation which required a systematic refinement of experimental conditions free from chromatography. Purification strategies were adjusted throughout the project to achieve maximal purity. Since column chromatography have proven to be limiting due to the high polarity of the target compound, solid-liquid and liquid-liquid extractions were employed as alternative methods. These methodologies not only enabled the efficient separation of the target compound from related impurities but were also more appropriate for large-scale applications. Furthermore, the antioxidant capacity of L-(+)-ergothioneine was compared with cysteine using the ABTS decolorization assay. The ABTS assay is a widely employed method for quantifying radical scavenging activity relative to Trolox, a vitamin E analogue, used as the standard antioxidant. We found that L-(+)-ergothioneine is efficient at scavenging ABTS•+ radical cations, similar to that of Trolox and cysteine. These results provide important information about the free radical scavenging activities of these derivatives and their potential nutraceutical, pharmaceutical and biomedical applications.

Keywords

ergothioneine

amino acid

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