Carbohydrates: Structure and Function

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Questions and Answers

What type of bond is formed when an aldose undergoes cyclization?

  • Covalent bond
  • Hemiacetal bond (correct)
  • Ether bond
  • Hemiketal bond

Which of the following compounds can form a hemiketal bond?

  • Ribose
  • Glucose
  • Fructose (correct)
  • Galactose

In the context of cyclization, what does the term 'intramolecular' refer to?

  • Reactions occurring within the same molecule (correct)
  • Reactions that involve free radicals
  • Reactions that occur in solution
  • Reactions between two different molecules

Which of the following represents the cyclized form of glucose?

<p>Glucopyranose (B)</p> Signup and view all the answers

What characterizes the cyclization of a ketose compared to an aldose?

<p>Ketoses form hemiketal bonds, while aldoses form hemiacetal bonds. (D)</p> Signup and view all the answers

Which of the following types of carbohydrates does NOT include glucose in its structure?

<p>Fructose (D)</p> Signup and view all the answers

What type of bond is formed during the creation of disaccharides like maltose?

<p>Glycosidic bond (D)</p> Signup and view all the answers

Which carbohydrate is characterized by both α(1 4) and α(1 6) glycosidic bonds?

<p>Starch (D)</p> Signup and view all the answers

What is the primary product of the dehydration process that forms glycosidic bonds?

<p>Water (A)</p> Signup and view all the answers

Which of the following disaccharides is composed of two glucose molecules linked by an α(1 4) bond?

<p>Maltose (C)</p> Signup and view all the answers

Which type of bond is found in cellulose, distinguishing it from starch?

<p>β(1 4) glycosidic bond (D)</p> Signup and view all the answers

Which carbohydrate serves as a storage form of glucose in animals?

<p>Glycogen (C)</p> Signup and view all the answers

What distinguishes fructose from other monosaccharides discussed?

<p>It is a ketone sugar unlike glucose, which is an aldose. (C)</p> Signup and view all the answers

Which sugar is classified as a reducing sugar and consists of two glucose units linked by a β(1-4) glycosidic bond?

<p>Cellobiose (D)</p> Signup and view all the answers

What distinguishes sucrose from maltose in terms of glycosidic linkage?

<p>Sucrose has an α(1-2) linkage. (A)</p> Signup and view all the answers

Which of the following foods are known to contain high amounts of glucose?

<p>Barley and fruit (C)</p> Signup and view all the answers

What is the structural difference in the anomeric carbon of glucose between maltose and cellobiose?

<p>Cellobiose has the OH pointing up at C1. (D)</p> Signup and view all the answers

Which sugar mentioned is a non-reducing sugar?

<p>Sucrose (A)</p> Signup and view all the answers

Which statement is true about cellobiose?

<p>It is formed from two glucose units. (D)</p> Signup and view all the answers

How is the structure of the β(1-4) glycosidic bond in cellobiose described?

<p>It represents a zig-zag formation. (C)</p> Signup and view all the answers

What is the main cleavage product of starch?

<p>Glucose (B)</p> Signup and view all the answers

What type of sugar is cellulose classified as?

<p>Non-reducing sugar (D)</p> Signup and view all the answers

Which type of linkage is primarily found in glycogen?

<p>α(1→4) linkages (A)</p> Signup and view all the answers

What structural feature of cellulose promotes hydrogen bonding?

<p>Flipping of glucose units (A)</p> Signup and view all the answers

Cellulose is a major component of which plant structure?

<p>Cell wall (B)</p> Signup and view all the answers

Glycogen is primarily stored in which type of animal tissue?

<p>Muscle tissue (A)</p> Signup and view all the answers

What is the primary function of glycogen in animals?

<p>Energy storage (C)</p> Signup and view all the answers

What is the primary structural similarity between glycogen and amylopectin?

<p>Both are glucose polymers with branching (A)</p> Signup and view all the answers

In cellulose, every other glucose unit is flipped over due to which type of linkages?

<p>β(1→4) linkages (D)</p> Signup and view all the answers

What type of polysaccharide is primarily used as an energy storage form in animals?

<p>Glycogen (A)</p> Signup and view all the answers

What type of hydrogen bonds are formed in cellulose due to its structure?

<p>Intra-chain and inter-chain hydrogen bonds (B)</p> Signup and view all the answers

Which sugar is the D-isomer when the OH on the bottom chiral center points to the right?

<p>Glucose (C)</p> Signup and view all the answers

What is the primary structural difference between enantiomers?

<p>They are mirror images of each other. (B)</p> Signup and view all the answers

What distinguishes epimers from other stereoisomers?

<p>They differ in configuration about one chiral center. (C)</p> Signup and view all the answers

Which two sugars differ specifically at the C4 position?

<p>D-glucose and D-galactose (B)</p> Signup and view all the answers

What type of ring structure do pentoses and hexoses form?

<p>Pyranoses and furanoses (B)</p> Signup and view all the answers

Which sugar is considered an epimer of D-glucose?

<p>D-mannose (D)</p> Signup and view all the answers

How many carbon atoms are present in a pyran structure?

<p>6 (D)</p> Signup and view all the answers

What is the shape of the furanose structure?

<p>Five-membered ring (C)</p> Signup and view all the answers

How many chiral centers does D-glucose have?

<p>4 (A)</p> Signup and view all the answers

What is the formula for both D-glucose and D-fructose?

<p>C6H12O6 (C)</p> Signup and view all the answers

What is the relationship between stereoisomers and the number of chiral carbons in a monosaccharide?

<p>Stereoisomers equal $2n$, where n is the number of chiral carbons. (D)</p> Signup and view all the answers

Which molecular structure represents the carbonyl group in D-fructose?

<p>A keto group (B)</p> Signup and view all the answers

What is the total number of stereoisomers for D-glucose?

<p>16 (B)</p> Signup and view all the answers

Which of the following best describes a chiral carbon atom?

<p>A carbon connected to four different groups (B)</p> Signup and view all the answers

What is the common characteristic of stereoisomers?

<p>They have the same molecular formula but different structural configurations. (C)</p> Signup and view all the answers

Flashcards

Aldohexose

A sugar with an aldehyde group as its most oxidized functional group.

Ketohexose

A sugar with a ketone group as its most oxidized functional group.

Stereoisomers

Molecules with the same chemical formula but different spatial arrangements of atoms.

Chiral Carbon

A carbon atom bonded to four different groups.

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Number of Stereoisomers

The number of stereoisomers is determined by the number of chiral carbons.

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Carbonyl Carbon

A carbonyl carbon atom is the carbon atom in the aldehyde or ketone group.

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Glucose

Glucose is an aldohexose with four chiral carbons.

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Structural Configuration

The stereoisomers of a monosaccharide differ in the spatial arrangement of the H and OH groups around the chiral carbons.

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Enantiomers

Stereoisomers of a monosaccharide with more than one chiral center. They are non-superimposable mirror images of each other. The D and L forms are determined by the configuration of the furthest chiral center from the aldehyde or ketone group.

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Epimers

Stereoisomers that differ only in the configuration around one chiral center.

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Hexoses

Sugars with six carbon atoms.

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Pentoses

Sugars with five carbon atoms.

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Pyranoses

Cyclic sugar forms resembling the organic compound pyran.

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Furanoses

Cyclic sugar forms resembling the organic compound furan.

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Bottom chiral center

The chiral center furthest away from the aldehyde or ketone group in a monosaccharide.

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D-Isomer

A monosaccharide with the -OH group on the bottom chiral center pointing to the right in a Fischer projection.

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Hemiacetal formation in monosaccharides

An intra-molecular reaction between an aldehyde group and an alcohol group within the same molecule, resulting in a cyclic structure called a hemiacetal.

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Hemiketal formation in monosaccharides

An intra-molecular reaction between a ketone group and an alcohol group within the same molecule, resulting in a cyclic structure called a hemiketal.

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Fisher Projection

A linear representation of a sugar molecule, showing the arrangement of atoms and functional groups in a chain structure.

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Monosaccharide

A type of carbohydrate that consists of a single sugar molecule.

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Disaccharide

A type of carbohydrate that consists of two sugar molecules linked together.

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Polysaccharide

A carbohydrate made up of many sugar units linked together.

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Glycosidic bond

A type of bond that links two sugar molecules together.

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α(1→4) glycosidic bond

A type of glycosidic bond that links two sugars together with a specific configuration, important in starch and maltose.

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β(1→4) glycosidic bond

A type of glycosidic bond that links two sugars together with a specific configuration, important in lactose and cellulose.

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α(1→2) glycosidic bond

A type of glycosidic bond that links two sugars together with a specific configuration, important in sucrose.

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Dehydration reaction

The process of forming a glycosidic bond by removing a water molecule.

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Maltose

A disaccharide formed by the condensation of two glucose molecules with an α(1→4) glycosidic bond.

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Cellobiose

A disaccharide formed by the condensation of two glucose molecules with a β(1→4) glycosidic bond.

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Reducing Sugar

A carbohydrate categorized as a reducing sugar because it has a free anomeric carbon.

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Anomeric Carbon

A sugar with a free anomeric carbon capable of forming an open chain structure.

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Beta (1->4) Linkage

The type of glycosidic bond that links the glucose units in cellulose. The bond direction is from carbon 1 to carbon 4, and the oxygen atom is orientated in a beta configuration.

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Alpha (1->4) Linkage

The type of glycosidic bond that links the glucose units in the main chain of glycogen. The bond direction is from carbon 1 to carbon 4, and the orientation is alpha.

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Alpha (1->6) Linkage

The type of glycosidic bond that creates the branches in glycogen. The bond direction is from carbon 1 to carbon 6, and the orientation is alpha.

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Polymer Structure

The specific arrangement of monomers in a polymer. It describes how the monomers are connected to each other and the spatial orientation of the bonds.

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Acidity

The ability of a molecule to donate a proton, or, more specifically, the tendency of a molecule to lose a hydrogen ion (H+) in solution.

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Electrophilic

A substance or entity that can readily accept or attract electrons from another chemical species to form a bond.

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Aldehyde group

A compound with an aldehyde group as its most oxidized functional group. This functional group has a carbonyl carbon atom bonded to one hydrogen atom and one alkyl or aryl group.

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Ketone group

A compound with a ketone group as its most oxidized functional group. This functional group has a carbonyl carbon atom bonded to two alkyl or aryl groups.

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Chiral molecule

A molecule that has an asymmetric carbon atom (a carbon atom that is bonded to four different groups). This results in the molecule having non-superimposable mirror images, known as enantiomers.

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Optical activity

The ability for a molecule to rotate the plane of polarized light, due to the presence of an asymmetric carbon atom.

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Pyranose ring

A structure with a ring formed from six carbon atoms. It is a common conformation of monosaccharides.

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Furanose ring

A structure with a ring formed from five carbon atoms. It is a common conformation of monosaccharides.

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Cyclization of sugars

The process of converting a linear sugar into a cyclic form.

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Ketone group

The functional group containing a carbonyl bond (C=O) in which the carbon atom of the carbonyl is attached to two alkyl or aryl groups.

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Aldehyde group

A functional group containing a carbonyl bond (C=O) where the carbon atom of the carbonyl is attached to one hydrogen atom and one alkyl or aryl group.

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Configuration

The specific arrangement of atoms in a molecule, including their spatial orientation.

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Fischer to Haworth conversion

The process of converting a Fischer projection into a Haworth projection.

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Study Notes

Carbohydrates: Types, Structure, Function, and Metabolism

  • Carbohydrates have the basic composition (CH₂O)ₙ
  • They are classified into four types: monosaccharides, disaccharides, oligosaccharides, and polysaccharides
  • Monosaccharides: Simple sugars with multiple hydroxyl (-OH) groups. They can be aldoses (aldehyde group) or ketoses (ketone group). Examples include glucose, fructose, galactose, and ribose. Their classification is based on the number of carbon atoms (e.g., triose, pentose, hexose)
  • Disaccharides: Two monosaccharides covalently linked by a glycosidic bond. Examples include sucrose, lactose, and maltose.
  • Oligosaccharides: A few (3-10) monosaccharides covalently linked by glycosidic bonds.
  • Polysaccharides: Polymers consisting of chains of more than 10 monosaccharides covalently linked by glycosidic bonds. Examples include starch (amylose and amylopectin), cellulose, and glycogen.

Sugar Nomenclature

  • The suffix "-ose" designates a carbohydrate
  • Prefixes like "tri," "tetra," "penta," and "hexa" indicate the number of carbon atoms in the monosaccharide.
  • Monosaccharides are named as aldoses or ketoses, depending on whether they have an aldehyde or a ketone group, respectively.

Monosaccharides: Aldoses and Ketoses

  • Aldoses have an aldehyde group, usually at C1
  • Ketoses have a ketone group, typically at C2

Stereoisomers (Isomers)

  • Stereoisomers: Monosaccharides with the same chemical formula but different spatial arrangements of atoms.
  • Chiral carbons are asymmetric carbon atoms attached to four different atoms or groups.
  • The number of stereoisomers for a monosaccharide is 2ⁿ, where n is the number of chiral carbons.

D and L Isomers

  • D and L isomers are stereoisomers relating to the asymmetric carbon atom farthest from the aldehyde or ketone group.
  • Most naturally occurring sugars are D isomers.

Epimers

  • Epimers are stereoisomers that differ only in the configuration about one chiral centre
  • Examples include D-mannose and D-galactose, which are epimers of D-glucose.

Cyclic Forms of Sugars

  • Haworth projections: Used to represent the cyclic forms of monosaccharides.
  • Fischer projections: Used to represent the open-chain forms of monosaccharides.
  • Anomers: Cyclized monosaccharides differing only at the anomeric carbon (C1 for aldoses, C2 for ketoses). Occur as alpha (α) and beta (β) forms. Mutarotation is the interconversion between these forms in solution.

Chair Configuration

  • The chair configuration represents the actual shape of the pyranose ring.

Monosaccharides: Glucose, Fructose

  • Glucose is an aldohexose; a six-carbon sugar with an aldehyde group
  • Fructose is a ketohexose; a six-carbon sugar with a ketone group

Disaccharides: Maltose, Sucrose, Lactose, Cellobiose

  • Maltose: Two glucose molecules linked by an α(1→4) glycosidic bond
  • Sucrose: Glucose and fructose linked by an α(1→2) glycosidic bond, a nonreducing sugar
  • Lactose: Galactose and glucose linked by a β(1→4) glycosidic bond, a reducing sugar
  • Cellobiose: Two glucose units linked by a β(1-4) glycosidic bond

Polysaccharides: Starch, Cellulose, Glycogen

  • Starch: Plants store glucose as amylose or amylopectin
  • Amylose: Linear glucose polymer with α(1→4) linkages
  • Amylopectin: Branched glucose polymer with α(1→4) and α(1→6) linkages
  • Cellulose: Linear glucose polymer with β(1→4) linkages, major constituent of plant cell walls
  • Glycogen: Animals store glucose as glycogen; highly branched glucose polymer with α(1→4) and α(1→6) linkages.

Digestion of Carbohydrates

  • Complex carbohydrates are broken down into simpler sugars via enzymatic hydrolysis.
  • Enzymes like amylase (saliva and pancreas), sucrase, lactase, and maltase break down disaccharides and polysaccharides into monosaccharides.

Glyco-conjugates

  • Glycolipids: Carbohydrates and lipids
  • Glycoproteins: Carbohydrates and proteins

Functions of Carbohydrates in Biological Systems

  • Energy source/storage
  • Cellular signaling and adhesion
  • Structural components (e.g., cellulose, chitin)
  • Diabetes mellitus
  • Lactose intolerance
  • Fructose intolerance
  • Galactosemia
  • Glycogen storage disease

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