Monosaccharide nomenclature

Figure 1.16 Monosaccharide nomenclature. Commonly used trivial names are given in the brackets...

Monosaccharides are the building blocks of larger sugars, and their biochemistry is possibly the most complex and confusing of all the biochemicals. Here is a brief list of the key terms in monosaccharide nomenclature for glucose ... 

See also Monosaccharide Nomenclature, Diastereomers, Saccharides, Mannitol... 

See also Saccharides, Structural Polysaccharides, Oligosaccharides, Monosaccharide Nomenclature, Biosynthesis of Polysaccharides (from Chapter 16), Biosynthesis of Other Polysaccharides (from Chapter 16), Biosynthesis of Amino Sugars (from Chapter 16), Biosynthesis of... 

See also Saccharides, Monosaccharide Nomenclature, Glucose, Galactose, Mannose... 

See also Galactose Operon, Galactose Metabolism, Diastereomers, Saccharides, cAMP Receptor Protein, Monosaccharide Nomenclature... 

See also Monosaccharide Nomenclature, Fructose Metabolism, Fructose-1,6-Aldolase B... 

The present Recommendations deal with the acyclic and cyclic forms of monosaccharides and their simple derivatives, as well as with the nomenclature of oligosaccharides and polysaccharides. They are additional to the Definitive Rules for the Nomenclature of Organic Chemistry [13,14] and are intended to govern those aspects of the nomenclature of carbohydrates not covered by those rules. 

The Haworth representation implies a planar ring. However, monosaccharides assume conformations that are not planar these may be represented by Haworth conformational formulae. The nomenclature of conformations is described in 2-Carb-7. For example, (5-D-glucopyranose assumes a chair conformation ... 

This is an abridged version of the document Conformational Nomenclature for Five- and Six-membered Ring Forms of Monosaccharides and their Derivatives. Recommendations 1980 [3],... 

This section relates to the introduction of a double or triple bond between two contiguous carbon atoms of the backbone chain of a monosaccharide derivative. A double bond between a carbon atom of the backbone chain and an atom outside that chain, or a double or triple bond between two carbon atoms outside the backbone chain, will be treated according to the normal rules of organic nomenclature [13,14],... 

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],... 

IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), Conformational nomenclature for five- and six-membered ring forms of monosaccharides and their derivatives (Recommendations 1980), Eur.J.Biochem. Ill, 295-298 (1980) Arch. Biochem. Biophys.,207,469-472(1981) PureAppl. Chem.,S3,1901-1905(1981) ref.2,pp. 158-161. 

IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), Nomenclature of branched-chain monosaccharides (Recommendations 1980), Eur. J. Biochem., 119, 5-8... 

Acetals, nomenclature, 123-124 cyclic, nomenclature, 121-122 Acid degradation, monosaccharides, 457-459 Acid hydrolysis... 

Haworth representation, cyclic monosaccharides, 61-63 Hemiacetal groups disaccharides with, 149-150 without, 148-149 nomenclature, 122-123 oligosaccharides with, 153-154 without, 151-153... 

A further complication that may be encountered in the nomenclature of branched-chain monosaccharides is in the numbering of the carbon atoms of the molecule. There is some precedent for numbering the carbon atoms of the branched moiety continuously with the carbon atoms of the main chain. However, this can result in confusion and ambiguity, especially when there are further substituents on the branched carbon atoms. In this connection, the Geneva system of nomenclature11 provides a reasonable solution, which is illustrated in the naming of compounds XII10 and XIII. 

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. 

Tentative rules for carbohydrate nomenclature. Part 1 J. Biol Chem. mi) 247, 613-634 Corrections, Eur. J. Biochem. (1972) 25, 4 Conformational nomenclature for five- and six-mem-bered ring forms of monosaccharides and their derivatives... 

Eur. J. Biochem. (1980) 111, 295-298 Nomenclature of unsaturated monosaccharides Eur. J. Biochem. (1981) 119, 1-3 Nomenclature of branched-chain monosaccharides Eur. J. Biochem. (1981) 119, 5-8 Abbreviated terminology of oligosaccharide chains /. Biol Chem. (1982) 257, 3347-3351 Polysaccharide nomenclature /. Biol Chem. (1982) 257, 3352-3354 Symbols for specifying the conformation of polysaccharide chains... 

The nomenclature and classification of monosaccharides is further complicated by the presence of chiral carbons within monosaccharides. In the late nineteenth century it was ascertained that the configuration of the last chiral carbon in each of the naturally occurring monosaccharides is the same as that for (-i-)-glyceraldehyde. This configuration was designated as D and it was determined that all naturally occurring monosaccharides were in the D configuration. 

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). 

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