Monosaccharides symbol

MALDI-MS spectra of released fV-glycans before (panel A) and after (panel B) a-Galactosidase digestion. Monosaccharide symbols are shown in O Table 1... 

NanoLC-ESI-MS of tryptically digested human IgG. The extracted chromatogram of the ion at m/z 1479 shows a signal at 15 minutes (upper panel). The lower panel shows the summation of all spectra acquired between 14 and 16 min. The resulting MS spectrum demonstrates the presence of several glycoforms of the peptide EEQYNSTYR. Monosaccharide symbols are shown in O Table 1... 

Lactose on hydrolysis gives glucose and an isomeric monosaccharide galactose, which may be given the symbol Ga-r. The lactose molecule may be represented as Ga-r-G-r, and it has therefore also a free potential aldehyde group and is a reducing sugar like maltose. 

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. 

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. 

Table 2. Symbols for monosaccharide residues and derivatives in oligosaccharide chains...

This is the form employed by the carbohydrate databank CarbBank, and is preferred for most purposes. Each symbol for a monosaccharide unit is preceded by the anomeric descriptor and the configuration symbol. The ring size is indicated by an italic / for furanose or p for pyranose, etc. The locants of the linkage are given in parentheses between the symbols a double-headed arrow indicates a linkage between two anomeric positions. In CarbBank, omission of a/p, D/L, or ftp means that this structural detail is not known. 

The hyphens may be omitted, except that separating the configurational symbol and the three-letter symbol for the monosaccharide. 

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 . 

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. 

Fig. 1. Number of trimers that can be generated from four monomer building blocks for nucleotides, peptides, and carbohydrates. The number of trisaccharides that can be generated in theory using four monosaccharide building blocks depends on what one wants to include. If => symbolizes the direction of the donor to the acceptor then two types of accessible trisaccharides can be envisaged (1) A=>B=>C and (2) A=>B< C. The number of possible combinations, in the absence of trehaloses, but including the possibility of a and j3 anomers is 83 x (4 x 4) for option 1 and 83 x (4 x 3) for option 2. Total number of possibihties is 14,336.

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. 

Table 1 Abbreviations and symbols used to indicate common monosaccharides.

Simple monosaccharides with four, five, six, and seven carbon atoms are called tetroses, pentoses, hexoses, and heptoses, respectively. These molecules have multiple asymmetric carbon atoms and, for these monosaccharides, ih symbols D and L designate the absolute configuration of the asymmetric carbon... 

These two nomenclature systems, the only ones which allow the position of the substituents on the constituent monsaccharides to be clearly indicated, are found particularly in articles on synthetic chemistry. They are awkward but can be simplified for free oligosaccharides. Each monosaccharide is represented by the following symbols Glc for glucose. Gal for galactose, Man for mannose. 

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...

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. 

Figure 1 The most common monosaccharides in the glycans of glycoproteins with corresponding structures and symbols. Most species other than humans may have iV-glycolyl as well as A-acetyl substitution on sialic acid. For sialic acid, R=CH0HCH0HCH20H.

Monosaccharide (shorthand symbol) Structural formula Representative occurrence... 

One/two-letter symbols for the proposed linear code (Banin et ai, 2002) are also included. The basic monosaccharide units are assigned by a single letter code for their common structures (e.g. G for D-Glcp, E for l>Fru/). Those fiiat are different from the common structure are expressed as follows, a) Opposite stereospecificity to the common structure is indicated wifii apostrophe , e.g. G for l-Glc/ , R for D-Ara/, b) Different ring structure to die common structure is indicated with e.g. G for d-G1c/, E for D-Fru/>, and c) Differences in both stereospecificity and ring structure is indicate wifii , e.g. G- for l-G1c/, R- for i>Ara >. 

Modifications are represented by adding square brackets that include the connecting position of the modification to the monosaccharide code, followed by the modification symbols (Table 6.2), e.g. D-Glcp-6-phosphate is written as G[6P]. Exceptions include monosaccharides with conunon modifications such as N-acetyl-D-glucosauuue (GN), A-acetyl-D-galactosauiiue (AN) and A-acetylneurauunic acid (NN). 

Lower case symbols are used to represeut conuectious (glycosidic linkages). Two components (anomer and linkage position) that desalbe a connection between two monosaccharide units are indicated. The letters a- and b-, representing a- and P-anomers, are followed by the number correspoudiug to their connection position. 

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