Outline

Introduction (Figure 9.1, Figure 9.2)

Monosaccharides

Monosaccharide Nomenclature

Aldoses and Ketoses (Figure 9.3, Figure 9.4)

Enantiomers (Figure 9.5, Structures)

Alternative Designations for Enantiomers: D-L and R-S (Figure 9.6)
Monosaccharide Enantiomers in Nature (Table 9.1)

Diastereomers

Tetrose Diastereomers (Figure 9.7, Figure 9.8)
Pentose Diastereomers (Figure 9.9a, Figure 9.9b)
Hexose Diastereomers (Figure 9.9a, Figure 9.9b)

Ring Structures

Pentose Rings (Figure 9.10, Figure 9.11, Table 9.2, Structure)
Hexose Rings (Structure, Figure 9.12, Figure 9.13)
Sugars with More Than Six Carbons (Table 9.1, Figure 9.14)

Derivatives of the Monosaccharides

Phosphate Esters (Table 9.3, Structure)

Acids and Lactones (Structure 1, Structure 2, Structure 3)

Alditols (Structure)

Amino Sugars (Structure 1, Structure 2, Structure 3, Table 9.4)

Glycosides (Structure, Figure 9.15)

Oligosaccharides

Oligosaccharide Structures (Table 9.5, Figure 9.16)

Distinguishing features of Different Disaccharides

1. The 2 Specific Sugar Monomers Involved and their Stereoconfigurations.

2. The Carbons Involved in the Linkage.

3. The Order of the Two Monomer Units, if Different

4. The Anomeric Configuration of the OH Group on Carbon 1 of Each Residue

Writing the Structure of Disaccharides (Structure, Table 9.5)

1. Sequence written starting with the nonreducing end at the left.

2. Anomeric and enantiomeric forms are designated by prefixes.

3. The Ring Configuration is Indicated by a Suffix

4. The Atoms Between Which Glycosidic bonds are Formed are indicated by Numbers in Parentheses Between Residue Designations.

Stability and Formation of the Glycosidic Bonds (Figure 9.17)

Polysaccharides

Storage Polysaccharides (Figure 9.19, Figure 9.20)

Structural Polysaccharides

Cellulose (Figure 9.21, Structure, Figure 9.22)

Chitin (Structure)

Glycosaminoglycans (Figure 9.23)

The Proteoglycan Complex (Figure 9.24b, Structure)

Nonstructural Roles of Glycosaminoglycans (Structure)

Bacterial Cell Wall Polysaccharides (Figure 9.25, Figure 9.26, Structure)

Glycoproteins (Table 9.6)

N-Linked and O-Linked Glycoproteins (Figure 9.28)

N-Linked Glycans (Structure)

O-Linked Glycans

Blood Group Substances (Figure 9.29, Table 9.7)

Oligosaccharides as Cell Markers (Figure 9.30)