松二糖, D-Turanose

Turanose belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Turanose exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Turanose has been detected in multiple biofluids, such as blood and urine. Within the cell, turanose is primarily located in the cytoplasm.

Turanose is a glycosylfructose isolated from Daphnia magna. It has a role as a Daphnia magna metabolite.

Turanose is a reducing analog of sucrose that is 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.

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)