Monosaccharides systematic names

The basis for the name is the structure of the parent monosaccharide in the acyclic form. Charts I and IV (2-Carb-10) give trivial names for parent aldoses and ketoses with up to six carbon atoms. 2-Carb-8.2 and 2-Carb-10.3 describe systematic naming procedures. 

Note 2. Since all aldoses up to the hexoses have trivial names that are preferred, the systematic names apply only to the higher aldoses. However, the configurational prefixes are also used to name ketoses (see below) and other monosaccharides. 

Several branched monosaccharides have trivial names, some established by long usage. Examples are given below, together with systematic names for the (cyclic or acyclic) forms illustrated. (See also the alphabetical listing of trivial names in the Appendix.) Enantiomers of the sugars listed should be named systematically. 

Monosaccharides are normally known by their traditional trivial names. EIow-ever, systematic names are in use. The systematic names of straight chain ... 

Trivial names are normally used for all types of polysaccharide. Systematic names may be used for small polysaccharides. These names are based on the systematic names of the monosaccharides corresponding to the residues. However, the suffix -osyl is used for a substituent residue joined through its anomeric carbon to the next residue in the chain and the suffix -oside is used for the last residue in the chain (Figure 1.19). Appropriate locants may or may not be used in systematic names. 

The following table lists the systematic names and symbols for selected carbohydrates and some of their derivatives. The symbols for monosaccharide residues and derivatives are recommended by lUPAC for use in describing the structures of oligosaccharide chains. A more complete list can be found in the reference. 

Pyranose and Furanose Names Cyclic structures of monosaccharides are named according to their five- or six-membered rings. A six-membered cyclic hemiacetal is called a pyranose, derived from the name of the six-membered cyclic ether pyran. A five-membered cyclic hemiacetal is called a furanose, derived from the name of the five-membered cyclic ether ran. The ring is still numbered as it is in the sugar, not beginning with the heteroatom as it would be in the heterocyclic nomenclature. These structural names are incorporated into the systematic names of sugars. 

For the simplified presentation of structures, abbreviations are used which usually consist of the first letters of the name of the monosaccharide. Figure 4.1 gives the configuration prefix derived from the trivial names, representing a specified configuration applied in monosaccharide classification. Thus, systematic names for D-glucose and D-fructose are D-gluco-hexose... 

The numbering of the positions of substitution of oligosaccharides uses the numbering of the carbons of individual monosaccharide units in the oligosaccharide, with the first unit in the systematic name being given numbers with primes. This is especially so for the nonreducing disaccharides. The order is unprimed numbers with the lowest numbers first, followed by the primed numbers with the... 

Through oxidation of the terminal aldehyde and alcohol functions of monosaccharides four different types of polyhydroxycarboxylic acids can be generated for which numerous traditional names are in use (see Table 17). Systematic names for these compounds, though, can very simply be formed by appropriate transformations or replacements of the. ..ose and. .. ulose endings as shown below ... 

Most sugars have their own specific common names, such as glucose, fructose, galactose, and mannose. These names are not systematic, although there are simple ways to remember the common structures. We simplify the study of monosaccharides by grouping similar structures together. Three criteria guide the classification of monosaccharides ... 

The common name of each monosaccharide indicates both the number of atoms it contains and the configuration at each of the stereogenic centers. Because the common names are firmiy entrenched in the chemicai literature, no systematic method has ever been estabiished to name these compounds. 

In the nomenclature of oligosaccharides, trivial names are still used for a number of substances (e.g. maltose, cellobiose or trehalose. Figure 4.5). In the case of reducing disaccharides, systematic nomenclature takes as its basis the name of the monosaccharide with a free hemiacetal hydroxyl group, which is preceded by the name of the substituted monosaccharide and the respective anomeric configuration is indicated (a- or P-). Disaccharide maltose (Figure 4.5), formed by condensation of... 

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