1. Figure: UN
Title:
D-Glucose and D-fructose.
Caption:
D-Glucose is a polyhydroxy aldehyde. D-Fructose is a polyhydroxy ketone.

3. Figure 15-27

4. Figure: UN
Title:
D-Glucose is oxidized to carbon dioxide and water.
Caption:
Plants produce D-glucose by photosynthesis.

5. Figure: UN
Title:
Polysaccharides consist of monosaccharide subunits.
Caption:
Polysaccharides are hydrolyzed to monosaccharides.

6. Figure: UN
Title:
(R)-(+)-Glyceraldehyde and (S)-(–)-glyceraldehyde.
Caption:
Glyceraldehyde can exist as a pair of enantiomers.

7. Figure: UN
Title:
D-Glyceraldehyde and L-glyceraldehyde.
Caption:
If the OH group is on the right on the bottom-most asymmetric center, then D is used. If the OH group is on the left on the bottom-most asymmetric center, then L is used.

8. Figure: UN
Title:
D-Galactose and L-galactose.
Caption:
If the OH group is on the right on the bottom-most asymmetric center, then D is used. If the OH group is on the left on the bottom-most asymmetric center, then L is used.

9. Figure: UN
Title:
Erythroses and threoses.
Caption:
Erythroses have the OH group on the same side. Threoses have the OH groups on opposite sides.

10. Figure: 21.1
Title:
Table Configurations of the D-aldoses.
Caption:
Aldotriose has one asymmetric center and two stereoisomers (one pair of enantiomers). Aldotetroses have two asymmetric centers and four stereoisomers (two pairs of enantiomers). Aldopentoses have three asymmetric centers and eight stereoisomers (four pairs of enantiomers). Aldohexoses have four asymmetric centers and sixteen stereoisomers (eight pairs of enantiomers).

11. Figure: UN
Title:
Examples of epimers.
Caption:
Diastereomers that differ in configuration at only one asymmetric center are called epimers.

12. Figure: UN
Title:
The Fischer proof, I.
Caption:
The D-sugars for aldohexoses each have an enantiomer.

13. Figure: UN
Title:
The Fischer proof, II.
Caption:
When (–)-arabinose is oxidized with nitric acid, the aldaric acid that results is optically active.

14. Figure: UN
Title:
The Fischer proof, III.
Caption:
Reversing the aldehyde and hydroxymethyl group gives a different sugar for structure 3.

15. Figure: UN
Title:
The Fischer proof, IV.
Caption:
Reversing the aldehyde and hydroxymethyl group gives the same sugar.

16. Figure: UN
Title:
The cyclization of D-glucose gives a-D-glucose and b-D-glucose.
Caption:
The anomeric carbon is position 1 in D-glucose.

17. Figure: UN
Title:
The cyclization of D-ribose forms a-D-ribose and b-D-ribose.
Caption:
The anomeric carbon is position 1 in D-ribose.

18. Figure: UN
Title:
a-D-Glucopyranose and a-D-ribofuranose.
Caption:
Six-membered rings in sugars are called pyranoses. Five-membered rings in sugars are called furanoses.

19. Figure: UN
Title:
Pyran and furan.
Caption:
Six-membered rings in sugars are called pyranoses. Five-membered rings in sugars are called furanoses.

20. Figure: UN
Title:
a-D-Fructofuranose, b-D-fructofuranose, a-D-fructopyranose, and b-D-fructopyranose.
Caption:
a-D-Fructofuranose, b-D-fructofuranose, a-D-fructopyranose, and b-D-fructopyranose are formed from the cyclization of D-fructose.

21. Figure: 21
Title:
Problem solved. Draw the cyclization of 4-hydroxybutanol.
Caption:
Both a and b are formed.

22. Figure: UN
Title:
a-D-Glucopyranose.
Caption:
In a-D-glucopyranose, the OH on carbon-1 is axial.

23. Figure: UN
Title:
b-D-Glucopyranose.
Caption:
In b-D-glucopyranose, the OH on carbon-1 is equatorial.

24. Figure: UN
Title:
a-D-Glucopyranose and b-D-glucopyranose.
Caption:
The b-D-glucopyranose (equatorial) is more stable than the a-D-glucopyranose (axial).

25. Figure: UN
Title:
a-D-Galactopyranose.
Caption:
The OHs on carbon-1 and carbon-4 are axial in a-D-galactopyranose.

26. Figure: UN
Title:
b-D-Gulose and b-L-gulose.
Caption:
b-D-Gulose is a mirror image of b-L-gulose.

27. Figure: UN
Title:
b-D-Glucopyranose is methylated to form ethyl b-D-glucopyranoside and ethyl a-D-glucopyranoside.
Caption:
The acetal or ketal of a sugar is called a glycoside.

28. Figure: UN
Title:
Mechanism for glycoside formation.
Caption:
The OH group bonded to the anomeric carbon becomes protonated in the acidic solution. A lone pair on the ring oxygen helps expel a molecule of water. Alcohol attacks from either side.

29. Figure: UN
Title:
Ball-and-stick model and chair conformation of the disaccharide maltose.
Caption:
Maltose is made from two D-glucopyranose molecules covalently bonded together via an a-1,4’-glycosidic linkage.

30. Figure: UN
Title:
Ball-and-stick model and chair conformation of the disaccharide cellobiose.
Caption:
Cellobiose is made from two D-glucopyranose molecules covalently bonded together via a b-1,4’-glycosidic linkage.

31. Figure: UN
Title:
Ball-and-stick model and chair conformation of the disaccharide lactose.
Caption:
Lactose is made from a D-glucopyranose molecule covalently bonded to a D-galactopyranose molecule via a b-1,4’-glycosidic linkage.

32. Figure: UN
Title:
Methylation of lactose.
Caption:
In the methylation of lactose, the only oxygens that are not methylated are in the glycosidic linkage. When the disaccharide is hydrolyzed, then those oxygens become attached to hydrogens.

33. Figure: UN
Title:
Ball-and-stick model and chair conformation of the disaccharide sucrose.
Caption:
Sucrose is made from a D-glucopyranose molecule covalently bonded to a D-fructofuranose molecule via an a-1,4’-glycosidic linkage.

34. Figure: UN
Title:
Subunits of amylose.
Caption:
Amylose is composed of unbranched D-glucopyranose units joined by a-1,4’-glycosidic linkages.

35. Figure: UN
Title:
Subunits of amylopectin.
Caption:
Amylopectin is composed of branched D-glucopyranose units joined by a-1,4’-glycosidic linkages and 1,6’-glycosidic linkages.

36. Figure: 21-00CO
Title:
The cell surface and an oligosaccharide.
Caption:
One of the functions of the oligosaccharide chains is to act as receptor sites on the cell surface.

37. Figure: 21.1
Title:
Figure Branching in amylopectin.
Caption:
The carbohydrate chains involve a-1,4’-glycosidic linkages, and the branch points each use an a-1,6’-glycosidic linkage.

38. Figure: 21.2
Title:
Figure Comparison of the branching in amylopectin and glycogen.
Caption:
When animals have more D-glucose than they need for energy, they convert the excess D-glucose to glycogen.

39. Figure: UN
Title:
Subunits of cellulose.
Caption:
Cellulose is composed of unbranched chains of b-1,4’-glycosidic linkages.

40. Figure: 21.3
Title:
Figure The a-1,4’-glycosidic linkages in amylose cause this polymer to form a left-handed helix.
Caption:
Many of the OH groups form hydrogen bonds with water molecules.

41. Figure: 21.4
Title:
Figure The b-1,4’-glycosidic linkages in cellulose form intramolecular hydrogen bonds, which cause the molecules to assemble in linear arrays.
Caption:
These large aggregates cause cellulose to be insoluble in water.

42. Figure: UN
Title:
Subunits of chitin.
Caption:
Chitin is composed of D-glucopyranose joined by b-1,4’-glycosidic linkages. Chitin also contains N-acetylamino groups instead of an OH group at the C-2 position.

43. Figure: UN
Title:
b-D-Ribose and b-D-2-deoxyribose.
Caption:
2-Deoxyribose is missing the OH at the C-2 position.

44. Figure: UN
Title:
Ball-and-stick model and chair conformation of gentamicin.
Caption:
Gentamicin is an antibiotic.

45. Figure: UN
Title:
Synthesis of L-ascorbic acid.
Caption:
L-Ascorbic acid (vitamin C) is synthesized from D-glucose in plants and in the livers of most vertebrates.

46. Figure: UN
Title:
Glycoproteins.
Caption:
Proteins bonded to oligosaccharides are called glycoproteins.

47. Figure: 21.5
Title:
Figure Blood type is determined by the nature of the sugar on the surface of the red blood cells.
Caption:
Each blood type is associated with a different carbohydrate structure.

48. Figure: UN
Title:
Saccharin, dulcin, acesulfame potassium, aspartame, sodium cyclamate, and sucralose.
Caption:
Saccharin, dulcin, acesulfame potassium, aspartame, sodium cyclamate, and sucralose are synthetic sweeteners.