JEE Challenger
More from Biomolecules

Structural Characterization of Disaccharide Rings and Glycosidic Linkages

The correct statement about the following disaccharide is

Diagram 0

Options

A

Ring (a) is pyranose with α\alpha-glycosidic link

Correct
B

Ring (a) is furanose with α\alpha-glycosidic link

C

Ring (b) is furanose with α\alpha-glycosidic link

D

Ring (b) is pyranose with β\beta-glycosidic link

Topics & Concepts

Step-by-Step Solution

To determine the correct statement about the given disaccharide, we analyze the structure of each ring:

  1. Ring (a):

    • Ring Size: Ring (a) consists of 5 carbon atoms and 1 oxygen atom forming a six-membered cyclic system. Therefore, it is a pyranose ring.
    • Anomeric Configuration (α\alpha or β\beta):
      • The −CH2OH-\mathrm{CH_2OH} group at C-5\text{C-5} points upwards (above the plane of the ring), which is characteristic of the D\text{D}-configuration.
      • The glycosidic substituent (−OCH2CH2O−-\mathrm{OCH_2CH_2O-}) at the anomeric carbon (C-1\text{C-1}) is directed downwards (below the plane of the ring).
      • Because the −CH2OH-\mathrm{CH_2OH} reference group at C-5\text{C-5} and the glycosidic oxygen at C-1\text{C-1} are located on opposite faces of the ring (trans to each other), the anomeric carbon has the α\alpha-configuration.
    • Thus, Ring (a) is a pyranose with an α\alpha-glycosidic linkage.
  2. Ring (b):

    • Ring (b) consists of 4 carbon atoms and 1 oxygen atom forming a five-membered cyclic system, meaning it is a furanose ring.
    • At the anomeric carbon (the ketal carbon on the left), the glycosidic oxygen is directed downwards while the −CH2OH-\mathrm{CH_2OH} is directed upwards.
    • The reference −CH2OH-\mathrm{CH_2OH} group at the far stereocenter (rightmost carbon) is directed downwards. Since the glycosidic oxygen and the reference −CH2OH-\mathrm{CH_2OH} group are on the same side (cis), this corresponds to a β\beta-glycosidic linkage, making statement C incorrect.

Therefore, the only correct statement is that Ring (a) is pyranose with an α\alpha-glycosidic link.

Correct Answer: A