Carbohydrate sulfates

It will be appropriate to consider first the building units of the carbohydrate residues and it will be immediately apparent that D-mannose and D-galactose with N-acetyl-amino sugars and hexuronic acids play a predominant role. It is proposed, therefore, to discuss briefly some of the more important discoveries connected with the two latter groups and with the carbohydrate sulfates. 

For obvious reasons of structural analogy to heparinoids the focus of this review is on sulfated carbohydrate derivatives. While it is not in all cases clear that these compounds really mimic the physiological activity of heparinoids, it is even less so for non-carbohydrate sulfates or sulfonates. Examples of the latter class include suramin and the simple 1,3-propanediol disulfate. Suramin is a sulfonat-ed bis-naphthalene derivative used as a drug to treat African trypanosomiasis and onchocerciasis (a filarial infection) it was also tested in a number of other indications including adrenocortical carcinomas and AIDS. A wider use is, however, restricted by various toxic effects [66]. 1,3-Propanediol disulfate reduced inflammation-associated amyloid progression in vivo after oral administration which may be relevant to the treatment of Alzheimer s disease [67]. 

Su ate esters. Baumgarten showed that the reagent sulfates substances such as hydrazine, diethylamine, phenol, and naphthalene. It has been used in preparation of carbohydrate sulfate esters, sterol sulfate esters, phenol sulfate esters. 2-Hydroxy-3-alkyl-l,4-naphthoquinone antimalarials can be separated from metabolites hydroxylated in the side chain by conversion of the hydroxylated metabolites into water-soluble sulfate esters and extraction with water. Hydroxy-hydrolapachol (1), which was identified as a metabolite of hydrolapachol and which... 

In view of the probable course of the addition reaction, it is not surprising that, besides mineral acids, acetic acid, trifluoroacetic acid, and acidic resins should catalyze the addition, or that efforts to detect carbohydrate sulfates amongst the products of the reaction catalyzed by sulfuric acid should have been unsuccessful. ... 

Sulfoglycosphingolipids (containing one or more carbohydrate-sulfate ester groups)... 

Pass G., Phillips G.O., WadlocK D.J., Morley R.G. "Interaction of Sulfated Polysaccharides with counterions", chapt. 17 of Carbohydrate Sulfates, R.G. Schweiger Ed., Am. Chem. Soc. Symp. 1878, 77. 

Carbohydrate sulfates are important in polysaccharide chemistry as several sulfated polysaccharides occur naturally in seaweeds, and human tissue contains heparin, the blood anticoagulating agent, a sulfated polysaccharide which also contains A -sulfate groups." Sulfation of polysaccharides by chlorosulfonic acid-pyridine leads to the incorporation of pyridinium substituents on a proportion of the reducing end groups. ... 

Diversity of Carbohydrate Sulfation 247 Table 1. Examples of sulfated monosaccharides found in glycoproteins or glycolipids. 

---