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...
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MDPI AG
2022-10-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/23/21/12827 |
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| author | Young Sung Jung Hyoung-Geun Kim Min-Cheol Lim Ji-Su Park Soonok Sa Miyoung Yoo |
| author_facet | Young Sung Jung Hyoung-Geun Kim Min-Cheol Lim Ji-Su Park Soonok Sa Miyoung Yoo |
| author_sort | Young Sung Jung |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-09T19:01:33Z |
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| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T19:01:33Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-568b9aa6cf6146b1983ee90bcb0fe7902023-11-24T04:57:50ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-10-0123211282710.3390/ijms232112827Synthesis of a New Glycoconjugate with Di-<i>ᴅ</i>-Psicose Anhydride StructureYoung Sung Jung0Hyoung-Geun Kim1Min-Cheol Lim2Ji-Su Park3Soonok Sa4Miyoung Yoo5Korea Food Research Institute, Wanju 55365, KoreaGraduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University, Yongin 17104, KoreaKorea Food Research Institute, Wanju 55365, KoreaKorea Food Research Institute, Wanju 55365, KoreaFood Biotech R&D Center, Samyang Corp., Seongnam 13488, KoreaKorea Food Research Institute, Wanju 55365, KoreaDemand 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.https://www.mdpi.com/1422-0067/23/21/12827anhydrous acidification<i>ᴅ</i>-allulosecaramelizationmetal chelationspiro-tricyclic disaccharide |
| spellingShingle | Young Sung Jung Hyoung-Geun Kim Min-Cheol Lim Ji-Su Park Soonok Sa Miyoung Yoo Synthesis of a New Glycoconjugate with Di-<i>ᴅ</i>-Psicose Anhydride Structure International Journal of Molecular Sciences anhydrous acidification <i>ᴅ</i>-allulose caramelization metal chelation spiro-tricyclic disaccharide |
| title | Synthesis of a New Glycoconjugate with Di-<i>ᴅ</i>-Psicose Anhydride Structure |
| title_full | Synthesis of a New Glycoconjugate with Di-<i>ᴅ</i>-Psicose Anhydride Structure |
| title_fullStr | Synthesis of a New Glycoconjugate with Di-<i>ᴅ</i>-Psicose Anhydride Structure |
| title_full_unstemmed | Synthesis of a New Glycoconjugate with Di-<i>ᴅ</i>-Psicose Anhydride Structure |
| title_short | Synthesis of a New Glycoconjugate with Di-<i>ᴅ</i>-Psicose Anhydride Structure |
| title_sort | synthesis of a new glycoconjugate with di i d i psicose anhydride structure |
| topic | anhydrous acidification <i>ᴅ</i>-allulose caramelization metal chelation spiro-tricyclic disaccharide |
| url | https://www.mdpi.com/1422-0067/23/21/12827 |
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