The stereochemical relationships, shown in Fischer projection, among the D-aldoses with three to six carbon atoms. The stereochemical relationships among the D-ketoses with three to six carbon atoms. The reactions of alcohols with (a) aldehydes to form hemiacetals and (b) ketones to form hemiketals. These reactions are freely reversible in aqueous solution. Cyclization of hexoses: anomerization The anomeric monosaccharides a-D-glucopyranose and b-Dglucopyranose, drawn as both Haworth projections and ball-andstick models Conformations of the cyclohexane ring (a) in the boat conformation and (b) in the chair conformation 4C 1 more stable 1C 4 less stable The two idealized chair conformations of b-D-glucopyranose Oxidized Monosaccharide Derivatives aldonic acid uronic acid D-Glucono-d-lactone and D-glucurono-d-lactone are, respectively, the lactones of D-gluconic acid and D-glucuronic acid. lactones The reversible oxidation of L-ascorbic acid to L-dehydroascorbic acid an a-ketoacid N-Acetyl-neuraminic (sialic) acid in its linear and pyranose forms The acid-catalyzed condensation of a-D-glucopyranose with methanol to form an anomeric pair of methyl D-glucopyranosides (Fischer glycosidation); furanosides also form under these conditions Common disaccharide: sucrose Common disaccharide: b-lactose Common disaccharide: b-maltose Common disaccharide: a-isomaltose Common disaccharide: b-cellobiose Electron micrograph of the cellulose fibers in the cell wall of the alga, Chaetomorpha melagonium Primary structure of cellulose: ......b-D-glucopyranosyl-(1,4)-b-D-glucopyranosyl-...... Extensive H-bonding network (intraand interchain: responsible for the rigidity of cellulose fibers Proposed structural model of cellulose O O Primary structure of chitin: ......b-D-GlcNAc-(1,4)-b-D-GlcNAc-...... A structural motif similar to that of cellulose: thus, similar physical properties (structure-function correlations) a-Amylose: D-glucose residues are linked by a-(1 4) bonds (red) ......a-D-glucopyranosyl-(1,4)-a-D-glucopyranosyl-...... a-Amylose: this regularly repeating polymer forms a left-handed helix. Amylopectin: Primary structure near one of it’s a-(1 6) branch points (red) Amylopectin showing its bushlike (compact, globular) structure (glucose residues at branch points indicated in red) Glycogen is amylopectin-like but with greater branching Photomicrograph showing the glycogen granules (pink) in the cytoplasm of a liver cell N-Linked oligosaccharides: all N-glycosidic protein attachments occur through a N-acetyl-b-Dglucosamine–Asn bond to Asn–X–Ser/Thr N-Linked oligosaccharides: N-linked oligosaccharides usually have the branched (mannose)3(NAG)2 core shown N-Linked oligosaccharides: some examples of N-linked oligosaccharides The microheterogeneous N-linked oligosaccharide of RNase B has the (mannose)5(NAG)2 core shown Some common O-glycosidic attachments of oligosaccharides to glycoproteins (red): blood group antigens (glycophorin) Disaccharide repeating units of the common glycosaminoglycans (proteoglycans): connective tissue; cartilage Hyaluronidase: a glycosidase that cleaves the b-(1,4) linkages of hyaluronic acid X-ray fiber structure of Ca2+ hyaluronate Proteoglycans: (a) Electron micrograph showing a central strand of hyaluronic acid. (b) Bottlebrush model of the proteoglycan aggrecan. Model of oligosaccharide dynamics in bovine pancreatic ribonuclease B (RNase B) Schematic diagram comparing the cell envelopes of (a) grampositive bacteria and (b) gram-negative bacteria Chemical structure of peptidoglycan of bacteria: the repeating unit of peptidoglycan Note the pentaglycine cross-linkages between the chains Lysozyme: a glycosidase that cleaves the b-(1,4) linkages of peptidoglycans Chemical structure of peptidoglycan: the S. aureus bacterial cell wall peptidoglycan Structure of penicillin: inhibits bacterial cell wall biosynthesis Enzymatic inactivation of penicillin Other bacterial cell wall antigenic groups Structure of teichoic acid Unusual monosaccharides occur in the O-antigens of gramnegative bacteria; are subject to rapid mutational alteration (new bacterial strains) END The surfaces of a normal mouse cell as seen in the electron microscope. The surfaces of a cancerous cell as seen in the electron microscope. Scanning electron micrograph of tissue from the inside of a human cheek. Properties of some proteoglycans