2-氨基-D-半乳糖, 2-Amino-D-galactose

2-Amino-D-galactose is a bacterial translocation inhibitor that is used as an experimental model to study the relationship between mitochondrial membrane potential and enzyme activities. This compound has been shown to be hepatoprotective in experimental models of hepatitis. It also inhibits the growth of bacteria and fungi by binding to their cell surface and causing disruption of their cell membranes. (2R,3R,4R,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal has a protective effect against autoimmune diseases such as type 1 diabetes and rheumatoid arthritis. The substance also has an effect on energy metabolism by increasing ATP content in mammalian cells.

Title: D-Galactosamine

CAS Registry Number: 7535-00-4

CAS Name: 2-Amino-2-deoxy-D-galactose

Additional Names: chondrosamine; GalN

Molecular Formula: C6H13NO5

Molecular Weight: 179.17

Percent Composition: C 40.22%, H 7.31%, N 7.82%, O 44.65%

Literature References: Amino sugar isolated from chondroitin sulfate, q.v.: P. A. Levene, F. B. La Forge, J. Biol. Chem. 18, 123 (1914). Sepn of a- and b-anomers: P. A. Levene, ibid. 57, 337 (1923). Synthesis: S. P. James et al., Nature 156, 308 (1945) eidem, J. Chem. Soc. 1946, 625; R. Kuhn, W. Kirschenlohr, Ann. 600, 126 (1956); P. A. Gent et al., J. Chem. Soc. Perkin Trans. 1 1972, 277. Chemistry: D. Horton in The Amino Sugars Vol. 1A, R. W. Jeanloz, Ed. (Academic, New York, 1969) pp 133-145. Inducer of exptl hepatitis: D. Keppler et al., Exp. Mol. Pathol. 9, 279 (1968); K. Decker, D. Keppler in Progress in Liver Diseases Vol. IV, H. Popper, F. Schaffner, Eds. (Grune & Stratton, New York, 1972) p 183. Powerful inhibitor of hepatic RNA synthesis: D. Keppler et al., J. Biol. Chem. 249, 211 (1974); T. Anukarahanonta et al., Eur. J. Cancer 16, 1171 (1980).

Derivative Type: Hydrochloride

Molecular Formula: C6H14ClNO5

Molecular Weight: 215.63

Percent Composition: C 33.42%, H 6.54%, Cl 16.44%, N 6.50%, O 37.10%

Properties: Crystals, mp 180° (dec). Shows mutarotation. a-Form: [a]D23 +124° ® +93° (water). b-Form: [a]D23 +47° ® +93° (water).

Melting point: mp 180° (dec)

Optical Rotation: a-Form: [a]D23 +124° ® +93° (water); b-Form: [a]D23 +47° ® +93° (water)