Monosaccharides, abbreviations

Symbols for the common monosaccharide residues and derivatives are listed in Table 2. They are generally derived from the corresponding trivial names. Abbreviations for substituents (see 2-Carb-1.16.2), preceded by locants, follow the monosaccharide abbreviations directly. 

Monosaccharide (Abbreviation) Examples (Abbreviation) Formula Mono- isotopic Average Mono- isotopic Average... 

Monosaccharide Abbreviation Monoisotopic mass Average mass... 

Oligosaccharide and polysaccharide structures occur not only in free form but often as parts of glycopeptides or glycoproteins [11] or of glycolipids [21]. It can be cumbersome to designate their structures by using the recommendations of 2-Carb-37. The use of three-letter symbols for monosaccharide residues is therefore recommended. With appropriate locants and anomeric descriptors, long sequences can thus be adequately described in abbreviated form. 

GalNAc, Gal, GlcNAc, Hex and HexNAc are the abbreviations used when discussing sequences of monosaccharides and represent A-acetylgalactosamine, galactose, A-acetylglucosamine, hexose, i.e. a monosaccharide with six carbon atoms, and A-acetylhexosamine, respectively. 

Abbreviations for amino acids, p. 60 For bases and nucleosides, p.80 For monosaccharides, p.38... 

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... 

Monomers are all 1,6-anhydroaldohexose derivatives. Parent monosaccharides are indicated by the conventional abbreviations, and maltose by Mai. Other symbols Ac, 3-O-acetyl An, 1,6-anhydro Bzl, benzyl Bbl, p-bromobenzyl Cro, 3-0-(2-butenyl) Ip, 3,4-O-isopropylidene and Xy, p-methylbenzyl (p-xylyl). 6 10 mole-% PF . 

TABLE 7-1 Abbreviations for Common Monosaccharides and Some of Their Derivatives... 

The symbol X in the Table means that an activated form of the monosaccharide is not known a dash shows that the monosaccharide has not been identified as a component of bacterial polysaccharides. For references, see the text. 6 See Ref. 101 for abbreviations. c Primary glycosyl nucleotide. 4 See comments in the text. 

Abbreviations for biosynthetic types are composed from abbreviations of nucleoside residues of activated forms of the monosaccharide components. 6 See footnote a to Table VI lin. and br. mean linear and branched polysaccharides. c Including other bacterial amphi-philes of Gram-negative, outer membranes. d Including amphiphiles of Gram-positive cell-membranes. 

The IUPAC-IUBMB short form symbolism18 2-Carb-38.5 is used here and elsewhere in this chapter for designation of oligosaccharide structures. Parent monosaccharide residues are the d enantiomers except for IdoA, which is the l enantiomer. Uronic acid residues modified by 44-unsaturation are prefixed by A4tS, and the associated anomeric symbol relates to the configuration at the 5-position of that residue before 4,5-elimination. The abbreviation HexA is used to denote either d-G1cA or L-IdoA. 

Depict their linkage and antennary structures using abbreviations for monosaccharide units. 

The Fischer projection is a convenient way of showing the configurations of the linear forms of monosaccharides. This convention depicts the concepts of stereochemistry established by Jacobus Henricus van t Hoff and Joseph Achille Le Bel in a simplified form. While these abbreviated structural formulas are simple to write and easy to visualize, there are some guidelines that should be taken into account when converting a three-dimensional structure into a Fischer projection and in its manipulation (Fig. 1.2) ... 

Figure 2 Mammalian monosaccharides and nucleotide sugars. (A) Chemical structures, common names, and abbreviations of the 11 monosaccharides found in mammalian glycans as well as ManNAc, the precursor for sialic acids. (B) Examples of the three classes of nucleotide sugars are provided by UDP-GIcNAc (Glc, GIcA, Gal, GalNAc, and Xyl also use UDP), GDP-Man (Fuc also is linked to GDP), and CMP-Neu5Ac/Gc (IdoA is produced by postsynthetic epimerization of GIcA and therefore does not require a nucleotide sugar).

Table 1 Abbreviations and symbols used to indicate common monosaccharides.

By establishing the stereochemical relationship between monosaccharides, Fischer was able to construct a family tree of carbohydrates. Figure 2.6 shows the tree for the D-series, together with their trivial names. Sometimes (especially in oligo- and polysaccharides), rather than full names abbreviated names consisting of the first three letters of their trivial names are used for pentoses... 

Monosaccharides Reducing sugar Polyol Food products Abbreviations... 

Fig. 1. Monosaccharide components of heparin/HS, with abbreviations and symbols, (a) Uronic acid residues, (fe) Glucosamine residues, with adjacent uronic acid units. Tlie display of variously substituted GlcN residues and adjacent units are based on reported HexA-GlcN and GlcN-HexA...

Monosaccharide residues are named and abbreviated (Table I) according... 

---