| D-Turanose[1] | |
|---|---|
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| IUPAC name |
(3S,4R,5R)-1,4,5,6-tetrahydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-one
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| Other names | α-D-glucopyranosyl-(1→3)-α-D-fructofuranose |
| Identifiers | |
| CAS number | 547-25-1 |
| PubChem | 5460935 |
| MeSH | turanose |
| SMILES |
C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]([C@@H]([C@@H](CO)O)O)C(=O)CO)O)O)O)O
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| Properties | |
| Molecular formula | C12H22O11 |
| Molar mass | 342.30 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Turanose is a reducing disaccharide. The D-isomer is naturally occurring. Its systematic name is α-D-glucopyranosyl-(1→3)-α-D-fructofuranose. It is an analog of sucrose not metabolized by higher plants, but rather acquired through the action of sucrose transporters for intracellular carbohydrate signaling. In addition to its involvement in signal transduction, D-(+)-turanose can also be used as a carbon source by many organisms including numerous species of bacteria and fungi.[2][3][4][5][6]
References
- ^ Turanose - Compound Summary, PubChem
- ^ Sinha, A.K., et al. (2002). "Metabolizable and non-metabolizable sugars activate different signal transduction pathways in tomato". Plant Physiol 128: 1480–1489. doi:. PMID 11950996.
- ^ Gonzali, S., et al. (2005). "A turanose-insensitive mutant suggests a role for WOX5 in auxin homeostasis in Arabidopsis thaliana". Plant J 44: 633–645. doi:.
- ^ Sivitz, A.B., et al. (2007). "Arabidopsis sucrose transporter AtSUC9. High-affinity transport activity, intragenic control of expression, and early flowering mutant phenotype". Plant Physiol 143: 188–198. doi:. PMID 17098854.
- ^ Loreti, E., et al. (2000). "Glucose and disaccharide-sensing mechanisms modulate the expression of α-amylase in barley embryos". Plant Physiol 123: 939–948. doi:. PMID 10889242.
- ^ D-Turanose at Sigma-Aldrich
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