9334. 5-Thio-d-glucose

Nomenclature

CAS number: 20408-97-3
5-Thio-α-d-glucopyranose; α-d-glucothiopyranose.
C6H12O5S; mol wt 196.22.
C 36.73%, H 6.16%, O 40.77%, S 16.34%.

Description and 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).

Chemical structure

Properties

Crystals from methanol, mp 135-136°. [α]D20 +188° (c = 1.56 in water). LD50 i.p. in mice: 5.5 g/kg (Schuman).

Use

Tool for examination of d-glucose biochemistry.