Abstract
Demand for healthy diets has led researchers to explore new saccharide as sucrose alternatives. ᴅ-Psicose, the C-3 epimer of ᴅ-fructose, has a similar sweetness intensity to sucrose but contributes fewer calories. This study proposes a disaccharide with a stable structure derived from ᴅ-psicose. The compound with a spiro-tricyclic core was generated at 32% conversion via caramelization of ᴅ-psicose under acidic anhydrous conditions. The compound was identified by high-resolution mass spectrometry and multi-dimensional nuclear magnetic resonance (NMR). The molecular formula was established as C12H20O10 from the molecular weight of m/z 324.1055. Twelve signals were observed by the 13C NMR spectrum. This compound, denoted di-ᴅ-psicose anhydride (DPA), exhibited a lower water solubility (40 g/L) and higher thermal stability (peak temperature = 194.7 °C) than that of ᴅ-psicose (peak temperature = 126.5 °C). The quantitatively evaluated metal ion scavenging ability of DPA was the best in magnesium (average 98.6 ± 1.1%). This synthesis methodology can provide disaccharides with high stability-reducing heavy metals.
Funder
Korea Ministry of Science and ICT
Subject
Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Computer Science Applications,Spectroscopy,Molecular Biology,General Medicine,Catalysis
Reference28 articles.
1. Sweet and umami taste: Natural products, their chemosensory targets, and beyond;Behrens;Angew. Chem. Int. Edit.,2011
2. Invited review: Sugar reduction in dairy products;McCain;J. Dairy Sci.,2018
3. Natural sweeteners: Sources, extraction and current uses in foods and food industries;Castro-Muñoz;Food Chem.,2022
4. Bioproduction of ᴅ-allulose: Properties, applications, purification, and future perspectives;Hu;Compr. Rev. Food. Sci. Food Saf.,2021
5. Psicofuranine. I. Discovery, isolation, and properties;Eble;Antibiot. Chemother.,1959