Biochemistry : Carbohydrate Structures and Functions

Study concepts, example questions & explanations for Biochemistry

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Example Questions

Example Question #1 : Glycosidic Linkages

Glucose polysaccharides are linked together at branch points in glycogen by what type of bond?

Possible Answers:

Beta-1,4 linkages

Peptide linkages

Beta-1,6 linkages

Alpha-1,6 linkages

Alpha-1,4 linkages

Correct answer:

Alpha-1,6 linkages

Explanation:

In glycogen, glucose molecules are attached one after the other by alpha-1,4 linkages. However, in order to make glycogen more compact for storage, branch points are created to created links between many shorter glucose polysaccharides. These branch points connect glucose molecules by alpha-1,6 linkages.

Example Question #1 : Glycosidic Linkages

Why does glycogen have more branches than starch?

Possible Answers:

There are more alpha-1,4 linkages

There are less alpha-1,6 linkages

There are less alpha-1,4 linkages

None of these answers; glycogen is not more branched than starch

There are more alpha-1,6 linkages

Correct answer:

There are more alpha-1,6 linkages

Explanation:

Lots of alpha-1,4 linkages allow for longer chain lengths in carbohydrates like starch and glycogen. However, it is the amount of alpha-1,6 linkages that determine the number of branches - since glycogen has many more alpha-1,6 linkages than starch does, it has more branches. This allows for easy breakdown of glycogen into glucose in the liver should there not be enough glucose in the body to supply the body's demand for energy production. Recall that glycogen phosphorylase can only break terminal alpha-1,4 glycosidic bonds; hence, with more branches there are more terminal glucose molecules that are substrates for this catabolic enzyme. 

Example Question #1 : Carbohydrate Structures And Functions

During times of glucose deprivation in the human body, the liver is able to supply glucose to the bloodstream by breaking down a large, branched polysaccharide that it holds in reserve until it is needed. Which of the following lists the correct type of glycosidic bonds found in this polysaccharide.

Possible Answers:

 for branch points and  for straight chain

 for branch points and  for straight chain

 for branch points and  for straight chain

  for branch points and  for straight chain

 for branch points and  for straight chain

Correct answer:

 for branch points and  for straight chain

Explanation:

For this question, we're told some background information about the liver's role in providing glucose homeostasis. We're told that when blood glucose levels are lowered, the liver is able to help restore glucose levels by keeping a large polysaccharide of glucose in store. In times of need, the liver can break this compound down to provide glucose to the bloodstream.

Even though the question doesn't explicitly tell us what the polysaccharide is, we should be able to infer that the compound in question is glycogen. Therefore, to answer the question, we need to know which kind of glycosidic bonds are found in glycogen.

First, let's recall that an individual glucose molecule is composed of six carbon atoms. In its ring form, glucose can exist as one of two epimers, depending on how its ring closes when transitioning from its straight chain form to its closed ring form. The anomeric carbon of the glucose molecule can be arranged in one of two ways when its ring closes. The anomeric carbon is the one that goes from being achiral to chiral as the ring closes. In the alpha configuration, the hydroxyl group attached to the anomeric carbon faces down, while in the beta configuration it faces up.

In addition to existing as either an alpha or a beta epimer, glucose also participates in glycosidic linkages using its first, fourth, and sixth carbon atom.

In glycogen, each individual glucose molecule is in the alpha configuration. Thus, we can rule out both answer choices that include beta. Moreover, the fourth carbon atom of each glucose molecule is attached to the first carbon atom (the anomeric carbon) in the next glucose molecule in the straight chain. To make branch points at various points along the straight chain, some of the glucose molecules have their sixth carbon atom attached to the anomeric carbon of other glucose molecules.

In conclusion,  glycosidic bonds are responsible for branch points and  glycosidic bonds are responsible for the straight chain.

Example Question #1 : Glycosidic Linkages

Glycogen is not a single chain of glucose units, but many chains branching off of one another. Why is the branching of glycogen important?

Possible Answers:

Branching increases the rate of glycogen synthesis

Branching increases the rate of glycogen degradation

Branching makes glycogen more compact

Branching increases glycogen solubility

All of these are reasons why glycogen branching is important

Correct answer:

All of these are reasons why glycogen branching is important

Explanation:

Because glycogen is so heavily branched, it is able to pack more glucose units together in a small space, thus it is more compact and has a greater solubility. Moreover, the branching allows for glycogen enzymes to act more efficiently on the chains of glucose, and so both degradation and synthesis have increased rates.

Example Question #1 : Glycosidic Linkages

You discover that your patient is lactose intolerant, having a mutation that does not allow them to produce an enzyme that cleaves the disaccharide lactose. If they had the lactase enzyme, which glycosidic bond would it cleave?

Possible Answers:

Glucose-alpha-1,4-glucose

Galactose-alpha-1,4-glucose

Glucose-beta 1,4-glucose 

Glucose-alpha 1,2-fructose

Galactose-beta-1,4-glucose 

Correct answer:

Galactose-beta-1,4-glucose 

Explanation:

lactose is made up of galactose and glucose and is bound via a beta 1,4 glycosidic bond. 

the enzyme lactase cleaves this bond to break down the sugar lactose. Maltose is glucose- alpha 1,4- glucose, and sucrose is glucose- alpha, 1,2- fructose. 

Example Question #1 : Carbohydrate Structures And Functions

What is an aldotriose?

Possible Answers:

A disaccharide that contains an aldehyde and three carbons

A disaccharide that contains three aldehydes and one carbon

A monosaccharide that contains three aldehydes and one carbon

A monosaccharide that contains both an aldehyde and three carbons

Correct answer:

A monosaccharide that contains both an aldehyde and three carbons

Explanation:

Aldotrioses are monosaccharides that contain both an aldehyde (an aldose) and three carbons (a triose). Knowing the definition of the word, and the breakdown of parts of the word, can help you recognize the molecule. The simplest aldotriose is glyceraldehyde.

A related concept involves ketotrioses, which are monosaccharides that contain both a ketone (a ketose) and three carbonds (a triose). Dihydroxyacetone is an example of a ketotriose.

Example Question #1 : Epimers, Chirality, And The Anomeric Carbon

Mirror-image stereoisomers are called __________.

Possible Answers:

diastereomers

enantiomers

epimers

anomers

Correct answer:

enantiomers

Explanation:

Enantiomers are chiral molecules that are non-superimposable mirror images of each other. Diastereomers result when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent stereocenters and are not mirror images of each other. An epimer is one of two stereoisomers that differ in configuration at only one stereocenter. An anomer is a type of epimer; it is one of two stereoisomers of a cyclic sugar that differs only in its configuration at the hemiacetal or acetal carbon (the anomeric carbon).

Example Question #2 : Carbohydrate Structures And Functions

Why is it that reducing sugars can be metabolized in humans, but non-reducing sugars cannot?

Possible Answers:

Because reducing sugars can bind to the proteins needed for metabolism, whereas non-reducing sugars cannot

Because only reducing sugars can traverse the cell membrane in order to enter cells where they can be metabolized, whereas non-reducing sugars cannot

Because reducing sugars can open their cyclic structure into the straight chain form, whereas non-reducing sugars cannot

Because humans lack the enzyme that degrades beta glycosidic linkages

Correct answer:

Because reducing sugars can open their cyclic structure into the straight chain form, whereas non-reducing sugars cannot

Explanation:

When it comes to metabolizing sugars, only reducing sugars are able to undergo breakdown. This is because reducing sugars are able to be converted from their closed chain form into their open chain form. It is only in the open chain form that sugars such as glucose can be metabolized.

Only reducing sugars can be converted into their open chain form. The reason for this is that the anomeric carbon for these sugars is not occupied. In their ring form, such sugars exist as hemiacetals that can readily and reversibly undergo chain opening. Additionally, some hemiketals can be converted into their open chain form, but they need to be able to tautomerize into their aldose form first.

Non-reducing sugars have their anomeric carbon tied up in a bond, and thus are locked in an acetal or ketal form. Consequently, they cannot convert into their open chain form, meaning that they cannot be metabolized.

Example Question #1 : Carbohydrate Structures And Functions

Which of the following statements about carbohydrates is true?

Possible Answers:

Glucose is a sugar with six hydroxyl groups and an aldehyde

Amylose makes up the major component of starch by mass

Sucrose is a reducing sugar

Polysaccharides have glycosidic bonds

None of the other statements is true

Correct answer:

Polysaccharides have glycosidic bonds

Explanation:

Glucose has five (not six) hydroxyl groups. Reducing sugars either have an aldehyde group or can form one through isomerism; sucrose doesn’t fit either description. Although there are more amylose molecules than amylopectin in starch, amylose is a minor component by mass; amylopectin makes up 70-80% of starch by mass. Polysaccharides are indeed joined in the union of two oses, which form glycosidic bonds.

Example Question #1 : Carbohydrate Structures And Functions

What functional groups are present on carbohydrates?

Possible Answers:

Carboxyl

Hydroxyl

Amide

Alcohol

Phosphate

Correct answer:

Carboxyl

Explanation:

Carbohydrate chains contain aldehyde or ketone functional groups, which are types of carboxyl groups. Remember the general formula for a carbohydrate is:  since they are hydrates (water) of carbon.

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