Problem Set 3

CARBOHYDRATES

1. Draw the structure and write the name of the product formed when α-D-Glucopyranose is added with NaBH4.
2. Draw the structure and write the name of the β anomer of the product formed when 2-deoxyribofuranose reacts with phosphoric acid
in C-5.
3. Draw the structure and write the name of the main org. product formed when α-D-Gulopyranose is added with Benedicts reagent.
4. Draw the structure and write the name of the main org. product formed when β-D-Idopyranose undergo oxidation of 10 alc. with an
Enzyme.
5. Draw the structure of the osazone formed when β-D-Xylofuranose is added with 2,4-dinitophenylhydrazine.
6. Draw the structure and write the name of the main org. product formed when α -D-Mannopyranose added with conc. nitric acid
7. Draw the structure of Raffinose. Raffinose is a trisaccharide where D-galactopyranose linked in an α-1,6 glycoside to D-glucopyranose
then the D-glucopyranose formed (β1→ β2) glycosidic linkage to fructofuranose.
8. 2,6-Dideoxy-D-altrose, also known as D-digitoxose, is a monosaccharide obtained from the hydrolysis of digitoxin, a natural product
extracted from purple foxglove (Digitalis purpurea). Digitoxin has found wide use in cardiology because it reduces pulse rate,
regularizes heart rhythm, and strengthens heart beat. Draw a structural formula for the open-chain form of 2,6-dideoxy-D-altrose.
9. Hyaluronic acid is the simplest acidic polysaccharide present in connective tissue. It is most abundant in embryonic tissues and in
specialized connective tissues such as synovial fluid, the lubricant of joints in the body, and the vitreous of the eye, where it provides a
clear, elastic gel that holds the retina in its proper position. Hyaluronic acid is also a common ingredient in lotions, moisturizers, and
cosmetics. It is composed of D-glucuronic acid joined by a β-1,3- glycosidic bond to N-acetyl-D-glucosamine, which is in turn linked to
D-glucuronic acid by a β-1,4-glycosidic bond. Draw a portion of Hyaluronic acid showing the two bonds (3 units only).
10. Differentiate starch, Cellulose, and glycogen. Discuss comprehensively.
11. Discuss comprehensively all the test for carbohydrates and give example each test.