D-核糖, D-Ribose

D-ribose (Rib) is an aldopentose, a component of RNA and a constituent of numerous cofactors, and certain vitamins. (Collins, 2006). Ribose is a component of bacterial polysaccharides found in Salmonella (Lindberg, 1990). Ribosylation leads to the production of significant amounts of advanced glycation end products, both extracellularly and intracellularly, it may be involved in cell dysfunction and subsequent cognitive impairments.

Title: D-Ribose

CAS Registry Number: 50-69-1

Molecular Formula: C5H10O5

Molecular Weight: 150.13

Percent Composition: C 40.00%, H 6.71%, O 53.29%

Literature References: Prepd by hydrolysis of yeast-nucleic acid: Levene, Jacobs, Ber. 42, 1201, 3247 (1909); Levene, Clark, J. Biol. Chem. 46, 19 (1921); Bredereck, Ber. 71, 408 (1938); Bredereck et al., ibid. 73, 956 (1940); Phelps, US 2152662 (1939 to U.S. Gov't); by ion-exchange resin chromatography: Cohn, Science 109, 377 (1949); J. Am. Chem. Soc. 71, 2275 (1949); 72, 1471 (1950). From glucose: Karrer, Helv. Chim. Acta 18, 1435 (1935); Austin, Humoller, J. Am. Chem. Soc. 56, 1152 (1934); Kuhn et al., Ber. 68, 1765 (1935); from nucleosides: Laufer, Charney, US 2379913; US 2379914 (both 1945 to Schwarz Labs.); from D-erythrose: Sowden, J. Am. Chem. Soc. 72, 808 (1950); from L-glutamic acid: Koga et al., Tetrahedron Lett. 1971, 263. Reduction of D-ribonic acid: van Ekenstein, Blanksma, Chem. Zentralbl. 1913, II, 1562; Steiger, Helv. Chim. Acta 19, 189 (1936). Review: Overend, Stacey, in Nucleic Acids vol. I, E. Chargaff, J. N. Davidson, Eds. (Academic Press, New York, 1955) pp 1-80.

Properties: Plates from abs alcohol, mp 87°. Shows complex mutarotation: Phelps et al., J. Am. Chem. Soc. 56, 748 (1934). Final [a]D24 -25° (water). Sol in water, slightly sol in alc.

Melting point: mp 87°

Optical Rotation: [a]D24 -25° (water)

Derivative Type: Phenylosazone

Molecular Formula: C17H20N4O3

Molecular Weight: 328.37

Percent Composition: C 62.18%, H 6.14%, N 17.06%, O 14.62%

Properties: Yellow needles from pyridine + water, mp 163-164°.

Melting point: mp 163-164°

Derivative Type: Methyl-D-riboside

Properties: Crystals from ethyl acetate, mp 83-84°. [a]D20 -113.6° (p = 3), Minsaas, Ann. 512, 286 (1934).

Melting point: mp 83-84°

Optical Rotation: [a]D20 -113.6° (p = 3), Minsaas, Ann. 512, 286 (1934)