Turanose

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]

d-Turanose[1]
Names
IUPAC name
α-D-glucopyranosyl-(1→3)-α-D-fructofuranose
Systematic 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
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.108
MeSH turanose
UNII
  • InChI=1S/C12H22O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4,6-16,18-21H,1-3H2/t4-,6-,7-,8-,9+,10-,11-,12-/m1/s1 ☒N
    Key: RULSWEULPANCDV-PIXUTMIVSA-N ☒N
  • InChI=1/C12H22O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4,6-16,18-21H,1-3H2/t4-,6-,7-,8-,9+,10-,11-,12-/m1/s1
    Key: RULSWEULPANCDV-PIXUTMIVBJ
  • 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
Properties
C12H22O11
Molar mass 342.30 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Turanose - Compound Summary, PubChem
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. D-Turanose at Sigma-Aldrich
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