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Chapter 8: Problem 9

Why is the \(\beta\)-D-glucopyranose form of glucose more abundant than \(\alpha\)-D-glucopyranose in aqueous solution?

Short Answer

Expert verified
The \(\beta\)-D-glucopyranose form of glucose is more abundant than \(\alpha\)-D-glucopyranose in aqueous solution due to its increased thermodynamic stability resulting from reduced steric hindrance in its structure.

Step by step solution

01

Understanding the Structure

Firstly, we need to understand that \(\alpha\)-D-glucopyranose and \(\beta\)-D-glucopyranose are anomers, differing in the configuration of the hydroxyl group at the anomeric carbon (C1). The \(\alpha\)-anomer has the hydroxyl group on the opposite side (trans) of the ring to the CH2OH group at C5, while the \(\beta\)-anomer has these two groups on the same side of the ring (cis).
02

Understanding the Stability

This difference in configuration means that the \(\beta\)-D-glucopyranose has a more favourable, less crowded conformation. This conformation results in less steric hindrance, reducing strain in the molecule, and makes it more thermodynamically stable than the \(\alpha\)-anomer.
03

Understanding the Equilibrium

When glucose is in an aqueous solution, the \(\alpha\) and \(\beta\) anomers exist in dynamic equilibrium, continuously interconverting between forms. The equilibrium favors the more stable \(\beta\)-D-glucopyranose, explaining its higher abundance in the solution.

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Most popular questions from this chapter

Describe the general structural features of glycosaminoglycans.

Identify each of the following: (a) Two aldoses whose configuration at carbons 3,4 , and 5 matches that of D-fructose. (b) The enantiomer of D-galactose. (c) An epimer of D-galactose that is also an epimer of D-mannose. (d) A ketose that has no chiral centers. (e) A ketose that has only one chiral center. (f) Monosaccharide residues of cellulose, amylose, and glycogen. (g) Monosaccharide residues of chitin.

Draw the structure of each of the following molecules and label each chiral carbon with an asterisk. (a) \(\alpha\)-D-Glucose 1-phosphate. (b) 2 -Deoxy- \(\beta\)-D-ribose 5 -phosphate. (c) D-Glyceraldehyde 3-phosphate. (d) L-Glucuronate.

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A carbohydrate-amino acid polymer that is a potent inhibitor of influenza virus has been synthesized. The virus is thought to be inactivated when multiple sialyl groups bind to viral surface proteins. Draw the chemical structure of the carbohydrate portion of this polymer (below, where \(X\) represents the rest of the polymer). NeuNAc \(\alpha-(2 \rightarrow 3)\) Gal \(\beta-(1 \rightarrow 4)\) Glu \(\beta-(1 \rightarrow)-X\)
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