1MonosaccharidesFigure 11-7 The two alternative chair conformations of β-D-glucopyranose.Voet&Voet, Biochemistry, chapter 11Cox, Lehninger Principles in Biochemistry, chapter 9, figure 3Variability due to chain length and stereochemistry of sugars2Cox, Lehninger Principles in Biochemistry, chapter 9, figure 3Cox, Lehninger Principles in Biochemistry, chapter 9, figure 1Oxy and deoxy-forms of sugars3Cox, Lehninger Principles in Biochemistry, chapter 9, figure 7Cyclic structures o the hexosesAldose KetoseFigure 11-4 Cyclization reactions for hexoses.Voet&Voet, Biochemistry, chapter 114Figure 11-5 The anomeric monosaccharides α-D-glucopyranose and β-D-glucopyranose, drawn as both Haworth projections and ball-and-stick models.Voet&Voet, Biochemistry, chapter 11Monosaccharides with 5 or more carbons form cyclic structures in solution 5%Cox, Lehninger Principles in Biochemistry, chapter 9, figure 9Glucose and its biologically important derivativesCytoplasmic form of free glucose5Cox, Lehninger Principles in Biochemistry, chapter 9, figure 9Glucose and its biologically important acidicglucose derivativesDisaccharides (sugars)6Cox, Lehninger Principles in Biochemistry, chapter 9, figure 11The glycosidic bond(maltose)Figure 11-12a Several common disaccharides. (a) Sucrose or fruit sugarVoet&Voet, Biochemistry, chapter 117Figure 11-12b Several common disaccharides. (b) Lactose or milk sugarVoet&Voet, Biochemistry, chapter 11Figure 11-12c Several common disaccharides. (c) Maltose or starch derived sugarVoet&Voet, Biochemistry, chapter 118PolysaccharidesFigure 11-13 Electron micrograph of the cellulose fibers in the cell wall of the alga Chaetomorpha melagonium.Voet&Voet, Biochemistry, chapter 11Cox, Lehninger Principles in Biochemistry, chapter 9, figure 13Schematic arrangement of sugar units in polysaccharides9Cox, Lehninger Principles in Biochemistry, chapter 9Figure 11-14 The primary structure of cellulose, a structurally important polysaccharidesVoet&Voet, Biochemistry, chapter 1110Stability in cellulose fibers is due to Intra-molecular hydrogen bonding in cellulose fibersVoet&Voet, Biochemistry, chapter 11X-ray structure of tetra-glucose in crystal latticeModel of cellulose structure with saturated H-bond network11Nature 426, 611 - 612 (11 December 2003); doi:10.1038/426611a Figure 1 Numbering system for carbon and oxygen atoms in two consecutive glucosylunits of cellulose. The O3–H...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.12Figure 11-16 Structure of chitin, a structurally important polysaccharideA homopolymer of N-acetyl-D-glucosaminewith β(1-4) glycosidic bondVoet&Voet, Biochemistry, chapter 11Cox, Lehninger Principles in Biochemistry, chapter 9, figure 14Energy storage polysaccharides: Glycogen (animals, bacteria) and starch (plants)Plants Animals13Figure 11-18a Amylopectin. (a) Its primary structure near one of its α(1 6) branch points (red).Figure 11-18bVoet&Voet, Biochemistry, chapter 11Figure 11-17a α-Amylose. (a) The D-glucose residues of α-amylose are linked by α(1 → 4) bonds (red). linear, only found in starchVoet&Voet, Biochemistry, chapter 1114Cox, Lehninger Principles in Biochemistry, chapter 9, figure 16Figure 11-17b α-Amylose. (b) This regularly repeating polymer forms a left-handed helix. Linear polymers with α-glycosidic bonds form helical conformationVoet&Voet, Biochemistry, chapter 11Figure 11-20 The disaccharide repeating units of the common glycosaminoglycans that make up extracellular matrix and connective tissueVoet&Voet, Biochemistry, chapter 1115Figure 11-22Proteoglycans.(a) Electron micrograph showing a central strand of hyaluronic acid. (b) Bottlebrush model of the proteoglycanaggrecan.Voet&Voet, Biochemistry, chapter 11Cox, Lehninger Principles in Biochemistry, chapter 2, figure 5 Bacterial cell wall polysaccharides16Figure 1-13 Simulated cross section of an E. coli cell magnified around one millionfold.Voet&Voet, Biochemistry, chapter 1Figure 11-24bCross-linked structure of peptidoglycan.(b)The S. aureus bacterial cell wall peptidoglycan.Voet&Voet, Biochemistry, chapter 1117Figure 11-24aChemical structure of peptidoglycan.(a) The repeating unit of peptidoglycan.Peptidoglycan unit from Salmonella typhimurium cell wall, a Gram-negative bacteriaUnusual amino acids and peptide bonds:Isoglutamate (side chain link)ε−amino linker to pentaglycine bridgeD-alaninVoet&Voet, Biochemistry, chapter 11Cox, Lehninger Principles in Biochemistry, chapter 9, figure 26Lipopolysaccharide (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
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