Title: 5-Thio-D-glucose
CAS Registry Number: 20408-97-3
CAS Name: 5-Thio-a-D-glucopyranose
Additional Names: a-D-glucothiopyranose
Molecular Formula: C6H12O5S
Molecular Weight: 196.22
Percent Composition: C 36.73%, H 6.16%, O 40.77%, S 16.34%
Literature References: The nearest analog of normal D-glucose available to date. Thought to interfere with cellular transport systems utilizing D-glucose due to this structural similarity. The first chemical other than a hormone or alkylating agent which can interfere reversibly with spermatogenesis and which also has been effective against malignant cultured cells. Prepn: M. S. Feather, R. L. Whistler, Tetrahedron Lett. 1962, 667; Rowell, Whistler, J. Org. Chem. 31, 1514 (1966); U. G. Nayak, R. L. Whistler, ibid. 34, 97 (1969); Abd El-Rahman, Whistler, Org. Prep. Proced. Int. 5, 245 (1973); H. Driguez, B. Henrissat, Tetrahedron Lett. 22, 5061 (1981). Pharmacology: D. J. Hoffman, R. L. Whistler, Biochemistry 7, 4479 (1968); R. L. Whistler, W. C. Lake, Biochem. J. 130, 919 (1972). Radioprotective effect on tissue in vivo: V. L. Schuman et al., Int. J. Radiat. Oncol. Biol. Phys. 8, 589 (1982). Brief review: Science 186, 431 (1974).
Properties: Crystals from methanol, mp 135-136°. [a]D20 +188° (c = 1.56 in water). LD50 i.p. in mice: 5.5 g/kg (Schuman).
Melting point: mp 135-136°
Optical Rotation: [a]D20 +188° (c = 1.56 in water)
Toxicity data: LD50 i.p. in mice: 5.5 g/kg (Schuman)
Use: Tool for examination of D-glucose biochemistry. |