Turanose
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 | |
Other names α-D-glucopyranosyl-(1→3)-α-D-fructopyranose | |
Identifiers | |
CAS number | 547-25-1 |
PubChem | 5460935 |
ChemSpider | 4574343 |
MeSH | turanose |
Jmol-3D images | {{#if:O=C([C@@H](O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)[C@H](O)[C@H](O)CO)CO|Image 1 |
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Properties | |
Molecular formula | C12H22O11 |
Molar mass | 342.30 g/mol |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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 (4): 1480–1489. doi:10.1104/pp.010771. PMC 154275. 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 (4): 633–645. doi:10.1111/j.1365-313X.2005.02555.x. PMID 16262712.
- ↑ 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 (1): 188–198. doi:10.1104/pp.106.089003. PMC 1761979. PMID 17098854.
- ↑ Loreti, E., et al. (2000). "Glucose and disaccharide-sensing mechanisms modulate the expression of α-amylase in barley embryos". Plant Physiol 123 (3): 939–948. doi:10.1104/pp.123.3.939. PMC 59056. PMID 10889242.
- ↑ D-Turanose at Sigma-Aldrich
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