2-Deoxy-D-glucose
Structural Formula Vector Image
Title: 2-Deoxy-D-glucose
CAS Registry Number: 154-17-6
CAS Name: 2-Deoxy-D-arabino-hexose
Additional Names: D-arabino-2-desoxyhexose; 2-deoxyglucose; 2-DG
Manufacturers' Codes: Ba-2758
Molecular Formula: C6H12O5
Molecular Weight: 164.16
Percent Composition: C 43.90%, H 7.37%, O 48.73%
Literature References: Antimetabolite of glucose, q.v., with antiviral activity. Synthesis: M. Bergmann et al., Ber. 55, 158 (1922); 56, 1052 (1923); J. C. Sowden, H. O. L. Fischer, J. Am. Chem. Soc. 69, 1048 (1947); H. R. Bolliger, Helv. Chim. Acta 34, 989 (1954); H. R. Bolliger, M. D. Schmid, ibid. 1597, 1671; H. R. Bolliger, "2-Deoxy-D-arabino-hexose (2-Deoxy-D-glucose)" in Methods in Carbohydrate Chemistry vol. I, R. L. Whistler, M. L. Wolfrom, Eds. (Academic Press, New York, 1962) pp 186-189. Inhibition of influenza virus multiplication: E. D. Kilbourne, Nature 183, 271 (1959). Effects on herpes simplex virus: R. J. Courtney et al., Virology 52, 447 (1973). Mechanism of action studies: M. R. Steiner et al., Biochem. Biophys. Res. Commun. 61, 745 (1974); E. K. Ray et al., Virology 58, 118 (1978). Use in human genital herpes infections: H. A. Blough, R. L. Giuntoli, J. Am. Med. Assoc. 241, 2798 (1979); L. Corey, K. K. Holmes, ibid. 243, 29 (1980). Effect vs respiratory syncytial viral infections in calves: S. B. Mohanty et al., Am. J. Vet. Res. 42, 336 (1981).
Properties: Cryst from acetone or butanone, mp 142-144°. [a]D17.5 +38.3° (35 min) ®+45.9° (c = 0.52 in water); +22.8° (24 hrs) ® +80.8° (c = 0.57 in pyridine).
Melting point: mp 142-144°
Optical Rotation: [a]D17.5 +38.3° (35 min) ®+45.9° (c = 0.52 in water); +22.8° (24 hrs) ® +80.8° (c = 0.57 in pyridine)
 
Derivative Type: a-Form
Properties: Cryst from isopropanol, mp 134-136°. [a]D26 +156° ® +103° (c = 0.9 in pyridine).
Melting point: mp 134-136°
Optical Rotation: [a]D26 +156° ® +103° (c = 0.9 in pyridine)
 
Use: Exptlly as an antiviral agent.

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