Sulphated glucosamine

The first anti-coagulant HS purified from a natural human extravascular source that has an important role in the rupture of the ovarian follicle at ovulation was shown to have 6% of 3-O-sulphated residues and the HS chains that do not bind AT exhibit and extremely high content of 3-O-sulphated glucosamine residues which suggested that they may exhibit... 

P. Lerouge, P. Roche, C. Faucher, F. Maillet, G. Truchet, J. C. Prome, and J. Denarie, Symbiotic host-specificity of Rhizohium meliloti is determined by a sulphated and acylated glucosamine oligosaccharide signal. Nature 344 781 (1990). 

Christgau S, Henrotin Y, Tanko LB, et al. Osteoarthritic patients with high cartilage turnover show increased responsiveness to the cartilage protecting effects of glucosamine sulphate. Clin Exp Rheumatol. 2004 22 36-42. 

ReginsterJY, Deroisy R, Rovati LC, et al. Long-term effects of glucosamine sulphate on osteoarthritis progression a randomised, placebo-controlled clinical trial. Lancet. 2001 357 251-256. 

Gottlieb, M. Conservative management of spinal osteoarthritis with glucosamine sulphate and chiropractic treatment. J. Manip. Physiol. Ther. 1997, 20 (6), 400-414. 

Heparin may be classified as a mucopolysaccharide on the basis that it contains glucosamine, but it has very distinctive properties, and it is better to recognize a separate class of natural compounds, the heparins or hepar-inoids. In this review, the term mucopolysaccharide is limited to the substances in Table 3.1, as distinct from the heparins and heparinoids, listed in Table 3.2. Sulphation of mucopolysaccharides results in heparinoids when the product resembles heparins in the chemical and biological properties included under definitions. An important biological difference is that the typical mucopolysaccharides, such as the chondroitin sulphuric acids, are the important structural materials of connective tissue, while the naturally... 

ChanNN, Baldeweg SE, Tan TMM, Hurel SJ. Glucosamine sulphate and osteoarthritis. Lancet (2001)357, 1618-19. 

Glucosamine and galactosamine are very commonly found in sulphated polysaccharides, and, of these, the chondroitin sulphates, dermatan sulphate and keratan sulphate are well known. Heparin and heparan sulphate are more complex polymers and are rather less well understood, but their synthesis has recently attracted a great deal of attention. All of these are considered in detail later in this chapter. 

Sulphate esters of glucosamine are found in keratan sulphate at C-6 and in heparin and heparan sulphate (at C-6- and some C-3-positions). Galactosamine is found as the 4-sulphate in chondroitin-4-sulphate and dermatan sulphate and as the 6-sulphate in chondroitin-6-sulphate it is always present as the A/-acetylamino sugar. Galactosamine substituted at C-3 has been found in a glycolipid of rat kidney(Tadano and Ishizuka, 1982). 

Sulphamido-groups (formerly called A -sulphates) are correctly specified as deoxy-sulphamido-residues. Hence the iV-linked sulphate found on glucosamine in heparinoids is described by 2-deoxy-2 sulphamido glucose , or, in jargon as glucosamine iV-sulphate. 

Heparan sulphate iV-Acetyl-D-glucosamine (partially sulphated) D-Glucuronic acid... 

Keratan sulphate Af-Acetyl-D-glucosamine (1 4 linkage, 6-SO4) D-Galactose (1 3 linkage)... 

Glucosamine is commercially available and widely used for joint pain in osteoarthritis. It has been reported to be associated with liver injury, ranging from mild elevations of serum transaminases to fulminant liver failure [20, 21, 22 sulphate]. 

---