Synthesis of a New Glycoconjugate with Di-<i>ᴅ</i>-Psicose Anhydride Structure
Demand for healthy diets has led researchers to explore new saccharide as sucrose alternatives. <i>ᴅ</i>-Psicose, the C-3 epimer of <i>ᴅ</i>-fructose, has a similar sweetness intensity to sucrose but contributes fewer calories. This study proposes a disaccharide with a stable...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-10-01
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| Series: | International Journal of Molecular Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-0067/23/21/12827 |
| Summary: | Demand for healthy diets has led researchers to explore new saccharide as sucrose alternatives. <i>ᴅ</i>-Psicose, the C-3 epimer of <i>ᴅ</i>-fructose, has a similar sweetness intensity to sucrose but contributes fewer calories. This study proposes a disaccharide with a stable structure derived from <i>ᴅ</i>-psicose. The compound with a spiro-tricyclic core was generated at 32% conversion via caramelization of <i>ᴅ</i>-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 C<sub>12</sub>H<sub>20</sub>O<sub>10</sub> from the molecular weight of <i>m</i>/<i>z</i> 324.1055. Twelve signals were observed by the <sup>13</sup>C NMR spectrum. This compound, denoted di-<i>ᴅ</i>-psicose anhydride (DPA), exhibited a lower water solubility (40 g/L) and higher thermal stability (peak temperature = 194.7 °C) than that of <i>ᴅ</i>-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. |
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| ISSN: | 1661-6596 1422-0067 |