Nomenclature, glycosides

The names of the individual compounds of this type are formed by replacing (a) the -ose of the systematic or trivial name of the aldose by -uronic acid , (b) the -oside of the name of the glycoside by -osiduronic acid or (c) the -osyl of the name of the glycosyl group by -osy luronic acid . The carbon atom of the (potential) aldehydic carbonyl group (not that of the carboxy group as in normal systematic nomenclature [13,14]) is numbered 1 (see 2-Carb-2.1, note 1). 

If the glycosidic oxygen link is replaced by -0-NH-, normal amino sugar nomenclature can be employed. 

Note. When the linkage between monosaccharide units is non-glycosidic (as in the phosphate derivative shown below), use of the glycan terminology is inappropriate other methods of polymer nomenclature should be employed [20],... 

The cyclic hemiacetal and hemiketal forms of monosaccharides are capable of reacting with an alcohol to form acetals and ketals (see Section 7.2). The acetal or ketal product is termed a glycoside, and the non-carbohydrate portion is referred to as an aglycone. In the nomenclature of glycosides we replace the suffix -ose in the sugar with -oside. Simple glycosides may be synthesized by treating an alcoholic solution of the monosaccharide with an acidic catalyst, but the reaction mixture usually then contains a mixture of products. This is an accepted problem with many carbohydrate reactions it is often difficult to carry out selective transformations because of their multifunctional nature. 

FIGURE 2.17 Ion nomenclature used for flavonoid glycosides (illustrated for apigenin 7-O-rutinoside). (Reprinted from Cuyckens, F. and Claeys, M., J. Mass Spectrom., 39, 1, 2004. Copyright 2004 John Wiley Sons, Ltd. With permission.)... 

The common nomenclature for di- or oligosaccharides specifies the order of monosaccharide units, the configuration at each anomeric carbon, and the carbon atoms involved in the glycosidic linkage (s). 

The subject of glycosylamines has already been reviewed in this Series,80 and the nomenclature of these compounds, formerly called JV-glycosides, amides, anilides, etc., was discussed. 

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