Turanose

Title: Turanose
CAS Registry Number: 547-25-1
CAS Name: 3-O-a-D-Glucopyranosyl-D-fructose
Additional Names: 3-(a-D-glucosido)-D-fructose
Molecular Formula: C12H22O11
Molecular Weight: 342.30
Percent Composition: C 42.11%, H 6.48%, O 51.41%
Literature References: Prepd from melezitose: Tanret, Compt. Rend. 142, 1424 (1906); Bridel, Aagard, Bull. Soc. Chim. Biol. 9, 884 (1927); Hudson, Pacsu, J. Am. Chem. Soc. 52, 2522 (1930); Pacsu in Methods in Carbohydrate Chemistry vol. I (Academic Press, New York, 1962) p 353. Structure: Isbell, Pigman, J. Res. Natl. Bur. Stand. 20, 787 (1938); Isbell, ibid. 26, 35 (1941); Hudson, J. Org. Chem. 9, 117, 470 (1944); Hassid, Ballou in The Carbohydrates, W. Pigman, Ed. (Academic Press, New York, 1957) p 508. Crystal structure: A. Neuman et al., Acta Crystallogr. B34, 242 (1978).
Properties: Nonhygroscopic prisms from water + alc. Very sweet taste. Dec 157°. Shows mutarotation. [a]D20 +27.3° ® +75.8° (c = 4 in water). Freely sol in water, methanol. One gram dissolves in 19 ml of 95% alc. Acid hydrolysis yields 1 mol D-glucose and 1 mol D-fructose. Reducing power about ½ of D-glucose.
Optical Rotation: [a]D20 +27.3° ® +75.8° (c = 4 in water)
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D-Turanose[1]
Turanose.png
Identifiers
CAS number 547-25-1 YesY
PubChem 5460935
ChemSpider 4574343
MeSH turanose
Jmol-3D images Image 1
Properties
Molecular formula C12H22O11
Molar mass 342.30 g/mol
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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]