Chemical Properties
(β form.) Colorless needles. Mp 110C
(decomposes). Very soluble in water; slightly soluble
in methanol and ethanol; insoluble in ether and
chloroform.
Occurrence
Glucosamine is found in mucopolysaccharides, chitin, and mucoproteins. Glucosamine is a naturally occurring substance; glucosamine sulfate is manufactured synthetically.
Definition
ChEBI: The open-chain form of D-glucosamine.
Preparation
Glucosamine can be prepared from shrimp exoskeletons[1].
Brand name
Adaxil;Antatril;Arthryl;Chitosamine;Corti-anartril;Dona 200-s;Dona compositum;Donna 200;Pona;Terramycin;Terrastatom;Tetracyn;Thiocondramine;Viartril.
World Health Organization (WHO)
Glucosamine is found in chitin, mucoproteins and
mucopolysaccharides. It is used as a pharmaceutical aid. Glucosamine sulfate has
been used in the treatment of rheumatic disorders though it is not widely marketed for this purpose.
Veterinary Drugs and Treatments
These compounds may be useful in treating osteoarthritis or other
painful conditions in domestic animals, but large, well-designed
controlled clinical studies proving efficacy were not located. One
study in dogs (McCarthy, O’Donovan et al. 2007) showed some positive
effect, but this study was not placebo controlled and compared
responses versus carprofen. Another placebo-controlled, blinded
study in dogs (Moreau, Dupuis et al. 2003), did not demonstrate
statistically significant improvement after 60 days of treatment.
These compounds potentially could be of benefit in cats with
FLUTD (feline lower urinary tract disease) because of the presence
of glycosaminoglycans as part of the protective layer of the urinary
tract. Controlled studies have shown some positive effects in some
cats, but overall did not appear to make a significant difference.
Purification Methods
Crystallise the amines from MeOH. The free base has been obtained from the hydrochloride (21.5g, see below) in a mixture of Et3N (15mL) and EtOH (125mL) by shaking for 2days at room temperature, and the solid Et3N.HCl is filtered off and the process repeated with more Et3N (3-4 times) until the D-glucosamine (15g) is free from Cl ions. It has m 88o , [] D20 +100o mutarotating to +47.5o (c 1, H2O). When Et2NH is used as base, the to conversion is complete giving D-glucosamine. The pentaacetate is purified by dissolving in CHCl3, treating with charcoal, drying (MgSO4), evaporating the solvent, and adding a little dry Et2O to induce crystallisation. It has m 124-126o, [] D +113o (c 1, CHCl3) after 16hours in a desiccator. [Leaback Biochemical Preparations 10 118 1963.] The N-acetyl derivative, m 203-205o from MeOH/Et2O (dry in vacuum P2O5) has [] D +75o to +41o (c 2, H2O); this derivative can also be purified by dissolving in the minimum volume of H2O to which is added 7-8volumes of EtOH followed by Et2O until turbid and keeping at ~20o to crystallise. Wash the crystals with MeOH then Et2O and dry in vacuo over P2O5. [Horton Biochemical Preparations 11 1 1966.]
References
[1]Liu, L., Liu, Y., Shin, H.-D., Chen, R., Li, J., Du, G., & Chen, J. (2013). Microbial production of glucosamine and N-acetylglucosamine: advances and perspectives. Applied Microbiology and Biotechnology, 97(14), 6149–6158.
https://doi.org/10.1007/s00253-013-4995-6
