Trehalulose
From Wikipedia, the free encyclopedia
| Names | |
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| IUPAC name
1-O-α-D-Glucopyranosyl-D-fructose | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.051.967 |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C12H22O11 | |
| Molar mass | 342.297 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trehalulose is a disaccharide made up of a molecule of fructose bound to a molecule of glucose. Like isomaltulose, it is a structural isomer of sucrose that is present in small quantities in honey.[1] It makes up 50% of sugars in the honeydew of silverleaf whiteflies[2][3] and is synthesised from sucrose by some bacteria,[4][5] such as Protaminombacter rubrum.[6][1] Because the anomeric carbon of the fructose moiety is not involved in the glycosidic bond, it is a reducing sugar.[6]
Because the fructose and glucose molecules are linked by a 1,1 glycosidic bond, which is more stable than the 1,2 glycosidic bond in sucrose, it is broken down more slowly than sucrose in the small intestine, giving it a lower glycemic index.[6] This more stable bond also means that it cannot be utilised by Streptococcus mutans, and it is therefore non-cariogenic.[7]
