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Chapter 8: Problem 1

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.

Short Answer

Expert verified
(a) D-erythrose and D-threose, (b) L-galactose, (c) D-glucose, (d) Dihydroxyacetone, (e) D-erythrulose, (f) D-glucose, and (g) N-acetyl-D-glucosamine.

Step by step solution

01

Identify Two Aldoses

An aldose is a monosaccharide (a simple sugar) with a carbonyl group at the end of the molecule, and D-fructose is one of them. Aldoses whose configuration at carbons 3, 4, and 5 matches that of D-fructose are D-erythrose and D-threose.
02

Identify the enantiomer of D-galactose

An enantiomer is a molecule that is a mirror image of another molecule. So the enantiomer of D-galactose is L-galactose.
03

Identify an Epimer of D-galactose and D-mannose

An epimer is a carbohydrate that differs only by configuration around one carbon atom. D-glucose is an epimer of D-galactose at C4 and an epimer of D-mannose at C2.
04

Identify a Ketose that has no Chiral Centers

A ketose is a sugar where the carbonyl group is within the molecule, typically at position 2. Dihydroxyacetone has no chiral centers.
05

Identify a Ketose that has Only One Chiral Center

A molecule with one chiral center is a simple sugar with four different groups attached to the carbon. D-erythrulose is an example of a ketose with only one chiral center.
06

Identify the Monosaccharide Residues of Cellulose, Amylose, and Glycogen

The monosaccharide residue for both cellulose, amylose, and glycogen is D-glucose.
07

Identify the Monosaccharide Residues of Chitin

The monosaccharide residue of chitin is N-acetyl-D-glucosamine.

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Most popular questions from this chapter

Describe the general structural features of glycosaminoglycans.

How many stereoisomers are possible for glucopyranose and for fructofuranose? How many are D sugars in each case, and how many are L sugars?

Honey is an emulsion of microcrystalline D-fructose and D-glucose. Although D-fructose in polysaccharides exists mainly in the furanose form, solution or crystalline Dfructose (as in honey) is a mixture of several forms with \(\beta\)-D-fructopyranose \((67 \%)\) and \(\beta\)-D-fructofuranose \((25 \%)\) predominating. Draw the Fischer projection for D-fructose and show how it can cyclize to form both of the cyclized forms above.

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In aqueous solution, virtually all D-glucose molecules \((>99 \%)\) are in the pyranose form. Other aldoses have a greater proportion of molecules in the open-chain form. D-Glucose may have evolved to be the predominant metabolic fuel because it is less likely than its isomers to react with and damage cellular proteins. Explain why D-glucose reacts less than other aldoses with the amino groups of proteins.
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