Sulfation, of polysaccharides

Nagasawa, K., Tohira, Y., Inoue, Y., and Tanoura, N., Reaction between carbohydrates and sulfuric acid Part I. Depolymerization and sulfation of polysaccharides by sulfuric acid, Carhohvdr. Res.. 18(1) (1971), 95-102. 

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. ... 

Metabolic Functions. Manganese is essential for normal body stmcture, reproduction, normal functioning of the central nervous system, and activation of numerous enzymes (126). Synthesis of the mucopolysaccharide chondroitin sulfate involves a series of reactions where manganese is required in at least five steps (127). These reactions are responsible for formation of polysaccharides and linkage between the polysaccharide and proteins that form... 

In tandem with his studies of polysaccharides, Stacey had a research group investigating the chemistry of the unusual sugars found as components of carbohydrate macromolecules. In this context, derivatives of simple sugars, di- and trisaccharides, uronic acids, deoxy sugars, amino sugars, sugar sulfates, and phosphates were studied. 

To gain an insight into the likely hydrolytic behavior of sulfated simple sugars and polysaccharides, Brimacombe, Foster, Hancock, Overend, and Stacey carried out a rigorous set of experiments with the cyclic sulfates of cyclohexane cis-and trims-1,2-diol as model compounds. The results were interpreted on the reasonable assumption that, in all cases, the cyclic sulfates initially afford a diol monosulfate. Examples of both S-0 and C-0 bond cleavage were encountered. A qualitative reaction mechanism was proposed for use as a working hypothesis for the hydrolysis of sugar sulfates. 

A variety of sulfating agents has been used for preparing sulfuric esters of polysaccharides.297 - 303 The methods employed include use of adducts of sulfur trioxide with such aprotic solvents as triethylamine,299 dimethyl... 

Once assignments of polysaccharide signals are known, they may be used as a basis in determination of the position of substitution by such groups as acetate, malonate, phosphate, and sulfate, whose a- and /3-shifts may be estimated by referral to suitable monosaccharide models. For phosphate, the phosphated carbon atoms and adjacent resonances may be identified, as they give coupled signals and are subject to lanthanide-induced shifts. These data are described in Section VI, 8. 

The third group of mucilages are all isolated from the seaweeds and are, in the main, salts of sulfate esters of polysaccharides, a large number of which have been isolated (see Table VII). In only one or two... 

Berteau, O. and Mulloy, B. (2003). Sulfated fucans, fresh perspectives Structures, functions, and biological properties of sulfated fucans and an overview of enzymes active toward this class of polysaccharide. Glycobiology 13, 29R-40R. 

A Didemnum sp. from Palau was the source of didemnaketal C (65), which contains a sulfonic acid group [95]. The in vitro anti-human immuodeficiency virus (anti-HTV) activity of D. molle from Pohnpei is associated with the sulfated mannose polysaccharide kakelokelose (66) [96],... 

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