Monosaccharides

Figure 11-7 The two alternative chair conformations of -D-glucopyranose.

Voet&Voet, Biochemistry, chapter 11

Variability due to chain length and stereochemistry of sugars

Cox, Lehninger Principles in Biochemistry, chapter 9, figure 3

Cox, Lehninger Principles in Biochemistry, chapter 9, figure 3

Oxy and deoxy-forms of sugars

Cox, Lehninger Principles in Biochemistry, chapter 9, figure 1

Cyclic structures o the hexoses

Aldose

Ketose

Cox, Lehninger Principles in Biochemistry, chapter 9, figure 7

Figure 11-4 Cyclization reactions for hexoses.

Voet&Voet, Biochemistry, chapter 11

Figure 11-5 The anomeric monosaccharides -D-glucopyranose and -Dglucopyranose, drawn as both Haworth projections and ball-and-stick models.

5%

Monosaccharides with 5 or more carbons form cyclic structures in solution

Voet&Voet, Biochemistry, chapter 11

Glucose and its biologically important derivatives

Cytoplasmic form of free glucose

Cox, Lehninger Principles in Biochemistry, chapter 9, figure 9

Glucose and its biologically important acidic glucose derivatives

Cox, Lehninger Principles in Biochemistry, chapter 9, figure 9

Disaccharides (sugars)

The glycosidic bond

(maltose)
Cox, Lehninger Principles in Biochemistry, chapter 9, figure 11

Figure 11-12a Several common disaccharides. (a) Sucrose or fruit sugar

Voet&Voet, Biochemistry, chapter 11

Figure 11-12b Several common disaccharides. (b) Lactose or milk sugar

Voet&Voet, Biochemistry, chapter 11

Figure 11-12c Several common disaccharides. (c) Maltose or starch derived sugar

Voet&Voet, Biochemistry, chapter 11

Polysaccharides

Figure 11-13 Electron micrograph of the cellulose fibers in the cell wall of the alga Chaetomorpha melagonium.
Voet&Voet, Biochemistry, chapter 11

Schematic arrangement of sugar units in polysaccharides

Cox, Lehninger Principles in Biochemistry, chapter 9, figure 13

Cox, Lehninger Principles in Biochemistry, chapter 9

Figure 11-14 The primary structure of cellulose, a structurally important polysaccharides

Voet&Voet, Biochemistry, chapter 11

Stability in cellulose fibers is due to Intramolecular hydrogen bonding in cellulose fibers

Voet&Voet, Biochemistry, chapter 11

Model of cellulose structure with saturated H-bond network

X-ray structure of tetra-glucose in crystal lattice

Figure 1 Numbering system for carbon and oxygen atoms in two consecutive glucosyl units of cellulose. The O3H...O5' hydrogen bond shown is present in all crystalline forms of cellulose, but the pattern of hydrogen bonding from O2 and O6 varies. Hydrogen atoms are shown in grey.
Nature 426, 611 - 612 (11 December 2003); doi:10.1038/426611a

Symmetry and directions of hydrogen bonding in cellulose, in which all chains are crystallographically identical but alternating glucose units in each chain, shaded grey and yellow, differ slightly in conformation.
Nature 426, 611 - 612 (11 December 2003); doi:10.1038/426611a

Figure 11-16 Structure of chitin, a structurally important polysaccharide

A homopolymer of N-acetyl-D-glucosamine with (1-4) glycosidic bond

Voet&Voet, Biochemistry, chapter 11

Energy storage polysaccharides: Glycogen (animals, bacteria) and starch (plants)

Plants

Animals

Cox, Lehninger Principles in Biochemistry, chapter 9, figure 14

Figure 11-18a Amylopectin. (a) Its primary structure near one of its (1 branch points (red).

6)

Figure 11-18b

Voet&Voet, Biochemistry, chapter 11

Figure 11-17a -Amylose. (a) The D-glucose residues of amylose are linked by (1 4) bonds (red). linear, only found in starch

Voet&Voet, Biochemistry, chapter 11

Figure 11-17b -Amylose. (b) This regularly repeating polymer forms a left-handed helix. Linear polymers with -glycosidic bonds form helical conformation

Cox, Lehninger Principles in Biochemistry, chapter 9, figure 16

Voet&Voet, Biochemistry, chapter 11

Figure 11-20 The disaccharide repeating units of the common glycosaminoglycans that make up extracellular matrix and connective tissue

Voet&Voet, Biochemistry, chapter 11

Figure 11-22 Proteoglycans. (a) Electron micrograph showing a central strand of hyaluronic acid. (b) Bottlebrush model of the proteoglycan aggrecan.

Voet&Voet, Biochemistry, chapter 11

Bacterial cell wall polysaccharides

Cox, Lehninger Principles in Biochemistry, chapter 2, figure 5

Figure 1-13 Simulated cross section of an E. coli cell magnified around one millionfold.

Voet&Voet, Biochemistry, chapter 1

Figure 11-24b

Cross-linked structure of peptidoglycan. (b) The S. aureus bacterial cell wall peptidoglycan.
Voet&Voet, Biochemistry, chapter 11

Figure 11-24a Chemical structure of peptidoglycan. (a) The repeating unit of peptidoglycan. Peptidoglycan unit from Salmonella typhimurium cell wall, a Gram-negative bacteria

Unusual amino acids and peptide bonds: Isoglutamate (side chain link)

amino linker to pentaglycine bridge D-alanin

Voet&Voet, Biochemistry, chapter 11

Lipopolysaccharide (LPS)
A glycolipid found in the outer membrane of Gram-negative bacteria; varies from strain to strain. Determines serotype of a bacteria and its infectivity, e.g. Escherichia coli O157:H7

Cox, Lehninger Principles in Biochemistry, chapter 9, figure 26