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Questions and Answers
What happens to a beam of plane-polarised light when it passes through a solution exhibiting optical activity?
What happens to a beam of plane-polarised light when it passes through a solution exhibiting optical activity?
What is the term for a mixture of equal amounts of dextrorotatory and laevorotatory isomers?
What is the term for a mixture of equal amounts of dextrorotatory and laevorotatory isomers?
What is the process of separating optically active isomers from a racemic mixture?
What is the process of separating optically active isomers from a racemic mixture?
What is the term for the carbon atom that becomes asymmetric after cyclization in a monosaccharide?
What is the term for the carbon atom that becomes asymmetric after cyclization in a monosaccharide?
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What is the term for a pair of cyclic compounds that are not mirror images of each other?
What is the term for a pair of cyclic compounds that are not mirror images of each other?
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What is the general formula of monosaccharides?
What is the general formula of monosaccharides?
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What is the classification of carbohydrates based on the number of carbon atoms?
What is the classification of carbohydrates based on the number of carbon atoms?
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What is the type of carbohydrate that cannot be hydrolyzed further into simpler forms?
What is the type of carbohydrate that cannot be hydrolyzed further into simpler forms?
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What is the general formula of disaccharides?
What is the general formula of disaccharides?
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What type of carbohydrates yields two molecules of the same or different molecules of monosaccharide on hydrolysis?
What type of carbohydrates yields two molecules of the same or different molecules of monosaccharide on hydrolysis?
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Study Notes
Carbohydrates
- Consist of covalently linked monosaccharide units, often associated with proteins (glycoproteins) and lipids (glycolipids) with structural and regulatory functions.
Polysaccharides (Glycans)
- Composed of more than 10 molecules of monosaccharides on hydrolysis, with a general formula of (C6H10O5)n.
- Have molecular masses ranging into millions of daltons and serve indispensable structural functions in all types of organisms.
- Most conspicuous in plants, where cellulose comprises up to 80% of dry matter.
Classification of Polysaccharides
- Divided into two groups: homopolysaccharides (homoglycans) and heteropolysaccharides (heteroglycans).
- Homopolysaccharides: polymers of same monosaccharide units, e.g. starch, glycogen, inulin, cellulose, dextrins, and dextrans.
- Heteropolysaccharides: polymers of different monosaccharide units or their derivatives, e.g. mucopolysaccharides (glycosaminoglycans).
General Properties of Carbohydrates
- Isomerism: due to asymmetric carbon atoms, compounds can exhibit stereoisomerism, resulting in isomers with identical composition but differing only in spatial configuration.
- D-Series and L-Series: the orientation of H and OH groups around the carbon atom determines whether a sugar belongs to D-series (OH group on the right) or L-series (OH group on the left).
- Most monosaccharides in mammals are D-sugars, and enzymes responsible for their metabolism are specific for this configuration.
Chemistry of Carbohydrates
- Carbohydrates or saccharides (Greek: sakcharon, sugar) have a chemical composition of “carbon hydrate” (CH2O)n, where n ≥ 3.
- Essential and most abundant class of biological molecules, with the basic units being monosaccharides.
- Aldehyde or ketone derivatives of higher polyhydric alcohols or compounds that yield these derivatives on hydrolysis.
Classification of Carbohydrates
- Divided into four major groups: monosaccharides, disaccharides, oligosaccharides, and polysaccharides.
Monosaccharides
- Also known as simple sugars, cannot be hydrolyzed further into simpler forms.
- Aldehyde or ketone derivatives of straight-chain polyhydroxy alcohols containing at least three carbon atoms, with a general formula of CnH2nOn.
Sub-classification of Monosaccharides
- Based on the number of carbon atoms: trioses, tetroses, pentoses, hexoses, etc.
- Based on aldehyde (– CHO) or ketone (– CO) groups: aldoses and ketoses.
Disaccharides
- Hydrolysis produces two molecules of the same or different monosaccharides, with a general formula of Cn(H2O)n-1.
- Examples include maltose, lactose, sucrose, and lactulose.
Oligosaccharides
- Composed of 3 to 10 monosaccharide units on hydrolysis.
Optical Activity of Carbohydrates
- Presence of asymmetric carbon atoms confers optical activity on compounds.
- Dextrorotatory (D or + sign) and laevorotatory (L or – sign) compounds rotate plane-polarized light to the right or left, respectively.
- Racemic mixtures: equal amounts of dextrorotatory and laevorotatory isomers, resulting in no optical activity.
- Resolution: separation of optically active isomers from a racemic mixture.
Cyclic Structures of Carbohydrates
- Formation of cyclic structures from open-chain forms of monosaccharides, resulting in anomers.
- Anomeric carbon atom: the carbon atom that becomes asymmetric after cyclization, leading to the formation of different anomers.
Biomedical Importance of Carbohydrates
- Energy source
- Structural functions
- Carbon skeleton
Optical Activity and Isomerism
- Presence of asymmetric carbon atoms confers optical activity on a compound.
- When a beam of plane-polarized light is passed through a solution exhibiting optical activity, it will be rotated to the right (dextrorotatory, D or + sign) or left (laevorotatory, I or – sign).
- A racemic mixture contains equal amounts of dextrorotatory and laevorotatory isomers, resulting in no optical activity.
- Resolution is the separation of optically active isomers from a racemic mixture.
Cyclic Structures and Anomers
- The reaction between an aldehyde group and an alcoholic-OH group on the same molecule forms a cyclic structure.
- This reaction can form two different forms of glucose: α-D-Glucose (OH group extends to the right) and β-D-Glucose (OH group extends to the left).
- Carbon-1 becomes asymmetric after cyclization and is called an anomeric carbon atom.
- Compounds related in this way are called anomers.
Biomedical Importance and Energy Structure
- Carbohydrates have both structural and regulatory functions in biological systems.
- They are associated with proteins (glycoproteins) and lipids (glycolipids).
- Polysaccharides consist of many covalently linked monosaccharide units and have molecular masses ranging from millions of daltons.
Polysaccharides
- Polysaccharides are composed of more than 10 molecules of monosaccharides on hydrolysis.
- General formula: (C6H10O5)n.
- They have indispensable structural functions in all types of organisms.
- Polysaccharides are further divided into two groups: homopolysaccharides (homoglycans) and heteropolysaccharides (heteroglycans).
Homopolysaccharides and Heteropolysaccharides
- Homopolysaccharides are polymers of the same monosaccharide units, e.g., starch, glycogen, inulin, cellulose, dextrins, and dextrans.
- Heteropolysaccharides are polymers of different monosaccharide units or their derivatives, e.g., mucopolysaccharides (glycosaminoglycans).
General Properties of Carbohydrates
- Isomerism: the presence of asymmetric carbon atoms in a compound gives rise to the formation of isomers.
- Stereoisomerism: compounds that are identical in composition and differ only in spatial configuration.
- D-Series and L-Series: the orientation of the H and OH groups around the carbon atom determines the series.
Chemistry and Structure of Carbohydrates
- Carbohydrates are also known as saccharides (Greek: sakcharon, sugar).
- They have the general formula (CH2O)n, where n ≥ 3.
- The basic units of carbohydrates are monosaccharides.
- Carbohydrates are essential and the most abundant class of biological molecules.
Classification of Carbohydrates
- Carbohydrates are divided into four major groups: monosaccharides, disaccharides, oligosaccharides, and polysaccharides.
- Monosaccharides are also known as simple sugars and cannot be hydrolyzed further into simpler forms.
- They have the general formula CnH2nOn.
Sub-classification of Monosaccharides
- Based on the number of carbon atoms: trioses, tetroses, pentoses, hexoses, etc.
- Based on the aldehyde or ketone groups: aldoses and ketoses.
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Description
This quiz covers the structure and function of monosaccharides and polysaccharides, including their relationship with proteins and lipids. Test your knowledge of carbohydrate chemistry!