Chondrosine ,  2-Amino-2-deoxy-3-O-(b-D-glucopyranuronosyl)-D-galactopyranose

2-Amino-2-deoxy-3-O-(b-D-glucopyranuronosyl)-D-galactopyranose monohydrate is a glycoside that is found in the testes. It has inhibitory properties on oligosaccharides and can be used to study the structure of glycoconjugates. 2-Amino-2-deoxy-3-O-(b-D-glucopyranuronosyl)-D-galactopyranose monohydrate has been shown to inhibit the enzyme hydrolase, which is involved in glycoprotein synthesis. 2ADOGP has also been shown to bind to human serum albumin, an abundant protein in human blood plasma that transports lipids, hormones, and other molecules throughout the body. This binding results in a decrease in the serum concentration of 2ADOGP after administration.

Title: Chondrosine

CAS Registry Number: 499-14-9

CAS Name: 2-Amino-2-deoxy-3-O-b-D-glucopyranurosyl-D-galactose

Additional Names: b-D-glucopyranosyluronic acid 2-deoxy-2-amino-D-galactose

Molecular Formula: C12H21NO11

Molecular Weight: 355.30

Percent Composition: C 40.57%, H 5.96%, N 3.94%, O 49.53%

Literature References: Disaccharide unit of chondroitins 4-sulfate and 6-sulfate. Isoln: Hebting, Biochem. Z. 63, 353 (1914); Levene, J. Biol. Chem. 140, 267 (1941); Wolfrom et al., J. Am. Chem. Soc. 74, 1491 (1952); Davidson, Meyer, ibid. 76, 5686 (1954). Structure: eidem, ibid. 77, 4796 (1955). Synthesis: Takanashi et al., ibid. 84, 3029 (1962). Chondrosine yields on acid hydrolysis chondrosamine (D-galactosamine, q.v.). Prepn and derivatives: Stacey, J. Chem. Soc. 1944, 272; Wolfrom, Onodera, J. Am. Chem. Soc. 79, 4737 (1957).

Properties: Crystals from aq ethanol. [a]D24 +40° (0.05 HCl). [a]D20 +39° (water). Dec on heating.

Optical Rotation: [a]D24 +40° (0.05 HCl); [a]D20 +39° (water)

Derivative Type: Methyl ester hydrochloride

Molecular Formula: C13H24ClNO11

Molecular Weight: 405.78

Percent Composition: C 38.48%, H 5.96%, Cl 8.74%, N 3.45%, O 43.37%

Properties: Crystals from hot ethanol, mp 159-161°. [a]D23 +42° (c = 2 in water).

Melting point: mp 159-161°

Optical Rotation: [a]D23 +42° (c = 2 in water)