Sulphated esters

White GF, KS Dodson, I Davies, PJ Matts, JP Shapleigh, WJ Payne (1987) Bacterial utilisation of short-chain primary alkyl sulphate esters. FEMS Microbiol Lett 40 173-177. 

The extremely attractive bright blue hue combined with excellent light fastness of Cl Reactive Blue 19 (7.37) remained unchallenged by competing blue reactive dyes for many years. The aqueous solubility of this structure is inherently low, depending only on the 2-sulphonate group after 1,2-elimination of the sulphate ester has taken place. This has led to... 

In many cases the monosaccharides found in these complex structures are present as one of their chemical derivatives, which may be an oxidation or reduction product, a phosphate or sulphate ester or an amino derivative, etc. However, these modified forms of monosaccharides may themselves have important biochemical roles and are not always found incorporated in polysaccharides. 

The phosphate esters and, to lesser extent, the sulphate esters of monosaccharides are very important naturally occurring derivatives. Metabolism of carbohydrates involves the formation and interconversion of a succession of monosaccharides and their phosphate esters of which glucose-1-phosphate and fruc-tose-6-phosphate are important examples. The sulphate esters of monosaccharides or their derivatives (usually esterified at carbon 6) are found in several polysaccharides, notably chondroitin sulphate, which is a constituent of connective tissues. 

Fekete M, Varszegi M, Kadar T, et al Effect of cholecystokinin octapeptide sulphate ester on brain monoamines in the rat. Acta Physiol Acad Sci Hung 57 37-46, 1981a... 

Above Illustrating adsorption of typical non-ionic disperse dye by cellulose triacetate. Below (Schematic) Illustrating loss of affinity of polar groups by screening effect of solvated water on ionic group, in a typical sulphate-ester dye. 

Isopropanol [67-63-0] M 60.1, b 82.5°, d 0.783, n25-8 1.3739. Isopropyl alcohol is prepared commercially by dissolution of propene in H2SO4, followed by hydrolysis of the sulphate ester. Major impurities are water, lower alcohols and oxidation products such as aldehydes and ketones. Purification of isopropanol follows substantially the same procedure as for n-propyl alcohol. 

Salts of the hydrogen sulphate esters of these higher alcohols are used extensively in the textile industries, those of the unsaturated alcohols possessing superior properties in certain respects. 

In the case of 2-phenylaziridine (4) the leaving group may originate from the hydroxyl function of 2-amino-1-phenylethanol by treatment with sulphuric acid to convert it into a sulphate ester which is then cyclised by treatment with base2 (Expt 8.1). 

Bowers, G. D. Higton,D. M. Manchee, G. R. Oxford,X Saynor,D. A. 1991. Thermospray liquid chromatography-mass spectrometry for the characterisation of sulphate ester conjugates. J. Chromatogr.,554,175-180. 

Todd, J. S., Zimmerman, R. C., Crews, P., and Alberte, R. S., The antifouling activity of natural and synthetic phenolic acid sulphate esters, Phytochemistry, 34, 401, 1993. 

D. A. Rees, Estimation of the relative amounts of isomeric sulphate esters in some sulphated polysaccharides,/. Chem. Soc. (1961) 5168-5171. 

A. G. Lloyd, K. S. Dodgson, R. G. Price, and F. A. Rose, Infrared spectra of sulphate esters. I. Polysaccharide sulphates, Biochim. Biophys. Acta, 46 (1961) 108-115. 

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