1. The stereochemical relationships, shown in Fischer projection, among the D-aldoses with three to six carbon atoms.

2. The stereochemical relationships among the D-ketoses with three to six carbon atoms.

3. The reactions of alcohols with (a) aldehydes to form hemiacetals and (b) ketones to form hemiketals. These reactions are freely reversible in aqueous solution.

4. Cyclization of hexoses: anomerization

5. The anomeric monosaccharides a-D-glucopyranose and b-D-glucopyranose, drawn as both Haworth projections and ball-and-stick models

6. Conformations of the cyclohexane ring (a) in the boat conformation and (b) in the chair conformation

7. The two idealized chair conformations of b-D-glucopyranose
more stable
less stable
The two idealized chair conformations of b-D-glucopyranose

8. 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.

9. The reversible oxidation of L-ascorbic acid to L-dehydroascorbic acid
lactones
The reversible oxidation of L-ascorbic acid to L-dehydroascorbic acid

10. N-Acetyl-neuraminic (sialic) acid in its linear and pyranose forms
an a-ketoacid
N-Acetyl-neuraminic (sialic) acid in its linear and pyranose forms

11. 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

12. Common disaccharide: sucrose

13. Common disaccharide: b-lactose

14. Common disaccharide: b-maltose

15. Common disaccharide: a-isomaltose

16. Common disaccharide: b-cellobiose

17. Electron micrograph of the cellulose fibers in the cell wall of the alga, Chaetomorpha melagonium

18. Primary structure of cellulose:
Primary structure of cellulose: b-D-glucopyranosyl-(1,4)-b-D-glucopyranosyl

19. Proposed structural model of cellulose
Extensive
H-bonding
network (intra-
and interchain:
responsible for
the rigidity of
cellulose fibers
Proposed structural model of cellulose

20. 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)

21. a-Amylose: D-glucose residues are linked by a-(1 ® 4) bonds (red)
......a-D-glucopyranosyl-(1,4)-a-D-glucopyranosyl

22. a-Amylose: this regularly repeating polymer forms a left-handed helix.

23. Amylopectin: Primary structure near one of it’s a-(1® 6) branch points (red)

24. Glycogen is amylopectin-like but with greater branching
Amylopectin showing its bushlike (compact, globular) structure (glucose residues at branch points indicated in red)
Glycogen is amylopectin-like but with greater branching

25. Photomicrograph showing the glycogen granules (pink) in the cytoplasm of a liver cell

26. N-Linked oligosaccharides: all N-glycosidic protein attachments occur through a N-acetyl-b-D-glucosamine–Asn bond to Asn–X–Ser/Thr

27. N-Linked oligosaccharides: N-linked oligosaccharides usually have the branched (mannose)3(NAG)2 core shown

28. N-Linked oligosaccharides: some examples of N-linked oligosaccharides

29. The microheterogeneous N-linked oligosaccharide of RNase B has the (mannose)5(NAG)2 core shown

30. Some common O-glycosidic attachments of oligosaccharides to glycoproteins (red): blood group antigens (glycophorin)

31. Disaccharide repeating units of the common glycosaminoglycans (proteoglycans): connective tissue; cartilage

32. X-ray fiber structure of Ca2+ hyaluronate
Hyaluronidase:
a glycosidase that
cleaves the b-(1,4)
linkages of
hyaluronic acid
X-ray fiber structure of Ca2+ hyaluronate

33. Proteoglycans: (a) Electron micrograph showing a central strand of hyaluronic acid. (b) Bottlebrush model of the proteoglycan aggrecan.

34. Model of oligosaccharide dynamics in bovine pancreatic ribonuclease B (RNase B)

35. Schematic diagram comparing the cell envelopes of (a) gram-positive bacteria and (b) gram-negative bacteria

36. Chemical structure of peptidoglycan of bacteria: the repeating unit of peptidoglycan

37. cross-linkages between the chains
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

38. Structure of penicillin: inhibits bacterial cell wall biosynthesis

39. Enzymatic inactivation of penicillin

40. Structure of teichoic acid
Other bacterial cell wall
antigenic groups
Structure of teichoic acid

41. Unusual monosaccharides occur in the O-antigens of gram-negative bacteria; are subject to rapid mutational alteration (new bacterial strains)

42. END

43. The surfaces of a normal mouse cell as seen in the electron microscope.

44. The surfaces of a cancerous cell as seen in the electron microscope.

45. Scanning electron micrograph of tissue from the inside of a human cheek.

46. Properties of some proteoglycans