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Structural Basis Classification Energy Reserves of Life Basic Metabolic Functions Metabolic Disorders Due to Carbohydrates Deficiency Diabetes Mellitus Structural Basis
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Carbohydrates, the prime most of the carbon compounds found in living tissues are biomacromolecules having a molecular weight of more than thousand Dalton. Structurally, carbohydrates are compound of aldehydes and ketones. Presence of hydroxyl groups gives uniqueness to their structure.
Carbohydrates are structurally classified into three types from the simplest monosaccharides to the complex polysaccharides.
Classification of carbohydrates starts from the simplest monosaccharides. They can be represented by the empirical formula of (C – H2O) n. ‘n’ denotes the number of carbon atoms. If a monosaccharide possess 3 carbon atoms (n = 3), it is a triose. Similarly a tetrose, pentose, hexose and heptose can be formed with 4, 5, 6 and 7 carbon atoms respectively. Monosaccharides can be further classified into two types, aldoses and ketoses based on their functional groups. Dihydroxyacetone, a triose is a well known example of ketose whereas glyceraldehyde is an aldose.
Enantiomers: Enantiomers are nonsuperimposable stereoisomers, which are indeed exact mirror images of each other. Except the tendency to rotate the plane-polarized light, two enantiomers possess similar physical and chemical properties in a symmetric environment. We can differentiate the two as (+) and (-) depending on its optical activity of rotating the plane-polarized light. (+) and (-) signs indicate the opposite directions. Hence while rotating the plane polarized light, the enantiomers do rotation which is equal in magnitude but opposite in directions. For example, if (+) enantiomer rotates the plane polarized light for say, 10 degrees in the right direction, then the (-) enantiomer rotates the plane polarized light for the same 10 degrees to the left.
Depending on the geometry of the isomers, enantiomers can be designated as ‘D’ and ‘L’ as prefixes in front of the name of their compounds. The well known monosaccharide, Glyceraldehyde which is an aldose consists of a single asymmetric carbon atom and hence has two enantiomers commonly denoted as D – glyceraldehyde and L – glyceraldehyde.
Fischer Projections: The figures depict the structure of D and L- Glyceraldehyde shown in Fischer projections. It was devised by Hermann Emil Fischer in 1891. The three dimensional view of a compound with an asymmetrical carbon can be easily drawn in two dimensions using this Fischer projection. A long vertical line in this represents the maximum lengthened continuous carbon chain. The carbon chain is oriented in such a way that the C1 carbon is at the top. All along the length of this vertical line, we can intersect with a series of horizontal lines to represent atoms or atom groups their ends. The point where the horizontal lines are intersecting the vertical line is considered as a carbon atom. Comparing the three dimensional view of molecules, the atoms or atom groups in Fischer projections which are shown at the ends of horizontal lines along the extension of the vertical line, has to be projected in front of the plane. The atoms which are along the vertical line have to be projected behind the plane.
The atoms behind the plane are shown by dotted wedges and the atoms in front of the plane are denoted by joined wedges. The joined line represents the atom within the plane. The simplest sugars of glucose and fructose tend to cyclize their open chain structure and form rings. These cyclic structures can be represented as follows
In D – glucose, the six membered ring of glucopyranose results as a formation of the hemiacetal group between the aldehyde group in 1st carbon and the hydroxyl group of 5th carbon present in the open chain structure. This formation of intramolecular hemiacetal is observed in aldoses.
In ketoses, there is a formation of intramolecular hemiketal. In the open chain structure of a ketohexose like D – Fructose, the keto group in 2nd carbon reacts with the hydroxyl group of 5th carbon resulting in the five membered cyclic ring of fructofuranose. Here, there is a possibility of formation of six membered cyclic ring also, called as fructopyranose resulting from reaction between C-2 keto group and C-6 hydroxyl group.
Anomers: Epimers are the sugars those which are having two different configurations at the single asymmetric carbon. Anomers are special types of epimers where the configuration differs only in the carbon atom bearing hemiacetal or hemiketal group. This carbon is designated as the anomeric carbon. In the formation of both glucopyranose and fructofuranose, two anomeric forms α and β are possible.
While representing them as α and β, α refers to the structure in which the hydroxyl group fastened to the C-1 atom is lying above the plane of the ring. Instead, if it is below the plane of the ring, it can be designated as β. These two forms are peculiarly known as anomers. Since their chemical structures are discrete from one another, the physical and chemical properties differ to a larger extent. Anomeric forms of glucopyranose are as follows
We can use the same α and β designations for fructose, where C-2 is the asymmetric carbon atom, α and β represent the hydroxyl groups attached to it.
This alpha and beta carbons can be interconverted into each other and this process is simply called as ‘anomerization’.
Haworth projections: Like Fischer projections, Haworth projections are used to represent the three dimensional view of the cyclic structure of monosaccharides. It was introduced by an English chemist Sir Walter N.Haworth.
In this depicted figure of α – D – fructofuranose, the atoms numbered from 1 to 6 are all carbon which is inherent. Here the anomeric carbon is C1.The hydrogen atoms on each carbon atom are also inbuilt and are not shown. The thicker line signifies that the atoms at its ends are at the close attention of the observer. Here C2 and C3 are at the closest view, C1 and C4 are farther and C5 is even farther than them.
Conformations: Structural arrangement of a particular molecule is called as ‘conformation’.
The monosaccharide glucose tends to form cyclic rings. The six membered ring pyranose is formed from the bond between the aldehyde (CHO) group present in the first carbon and fifth carbon atom to form a complete ring. Chair and boat shape are the well known conformations of molecules. The stability of glucose molecule is more on its structural arrangement in a chair shaped conformation since all their axial positions are in use by hydrogen atoms. Glycosidic bonds: Glycosidic bond is a special type of covalent chemical bond which joins two simple monosaccharides. It can be classified as two kinds, one of which is the alpha glycosidic
bond where the bond is formed below the plane of the ring. The other is a beta glycosidic linkage where the bond is above the plane of the ring.
Monosaccharides can easily be linked with amines and alcohols through these specific glycosidic bonds. In case of amines, the bond is formed between the anomeric carbon of sugar and nitrogen atom of the amine and termed as N – glycosidic bond. While in alcohols, the bond formed is O – glycosidic bond which is the link between the oxygen atom of the hydroxyl group in alcohol molecule and the anomeric carbon of sugar. This reaction provides an exclusive modification to monosaccharides enabling them to form nucleosides which later bond with phosphoric acid to form nucleotides, the back bone of DNA and RNA.
Oligosaccharides are sugars having two or more monosaccharide units. The glycosidic links between the adjacent atoms of their molecules enabling this group of molecules possible. Glucose and fructose are "single" sugars or monosaccharides. A disaccharide is formed if these two monosaccharides are linked together by an O –glycosidic linkage.
Disaccharides are also termed as ‘double sugars’. Maltose, sucrose and lactose are well known disaccharides. Maltose is formed by the linkage of two glucose molecules whereas sucrose is formed from glucose and fructose. Lactose is a sugar in milk and is formed by the beta -1, 4 -glycosidic linkage between the two simple sugars glucose and galactose.
Even the formation of a disaccharide unit is complex, in simple terms it involves the formation of a glycosidic linkage between the two sugar units. The process of dehydration (i.e.) removal of a water molecule occurs when one of the monosaccharides loses its hydrogen atom and the other donates its hydroxyl group. Similarly, a large variety of oligosaccharides are possible facilitated by the formation of glycosidic bonds.
Polysaccharides are one among the most important macromolecules formed by the polymerization of simple monosaccharide or sugar units. Almost all the naturally found carbohydrates are in the form of polysaccharides having higher molecular weights. Different types of polysaccharides are known as mannose, xylose and arabinose. The monomeric units differ in each polysaccharide, but the dominant monosaccharide is Dglucose.
If these building units are all similar, as in the case of cellulose which is formed by the merging of the same sugar ‘glucose’, it is designated as a homopolymer. Similarly ‘starch’ is the homopolymer made of glucose. The homopolymer formed by ‘fructose’ units is Inulin. Inulin is found widespread in plant carbohydrates as storage reserves. Our gastrointestinal tract doesn’t have the ability to digest Inulin and hence they provide us less calorie. Due to this property, inulin is consumed widely in food industry for low calorific nutritive and healthy foods. Starch is the major form of stored food reserves in cells of plants. Two types of starches are found based on structure. Amylose is the unbranched structure which consists of a long linear chain of hundreds of glucose residues. Branched starch comprised of thousands of glucose residues is called amylopectin. Approximately every thirtieth residue contains a short side chain linked to the main chain by a glycosidic bond. Glycogen is the glucose storage polymer used in animals. When compared with amylopectin, its structure is similar, but is more highly branched. About every tenth glucose unit contains a side chain. The degree of branching in these polysaccharides can be measured through chemical or enzymatic analysis. Liver and skeletal cells deserve the major part of glycogen in animals.
The property of insolubility in water lets them serve as the major storage reserves. Plants accumulate their excess glucose in the form of starch which provides the major nutrition in human diet.
Wood, cotton and paper are all consist of cellulose which is the single most plentiful organic molecule in the world. Plant cell walls maintain their structure with the help of cellulose only. Both starch and cellulose are made of same monomeric units of glucose, but they differ in which cellulose possess no side chains. This linear structure enables it to give a strengthened structure, with all the linear molecules lay close together. Most of the animals, including humans cannot digest cellulose and hence it functions as roughage and is eliminated out during excretion largely unaffected. Some animals like cow have intestinal microorganisms that break down cellulose into monosaccharide nutrients with the help of beta-glycosidase enzymes. Next to cellulose, the abundantly found polysaccharide in nature is chitin. It is a complex heteropolymer which is made of modified sugars and amino acids. The most important constituent of chitin is the amino sugar N – Acetylglucosamine. It forms the composition of exoskeletons of many species of crustaceans like lobsters and crabs. It is commonly found as complexes with other proteins and polysaccharides. In structure of chitin, two N – Acetylglucosamine components are repeated along the whole chain forming beta-1, 4 linkages. Both chitin and cellulose serve; to increase the structure and strength, thus giving protection to the organisms. Chitin is used widely for chemical and industrial purposes. In paper industries, chitin is employed to improve the strength of the paper. Its flexibility and strength fix it as the suitable material for making the surgical threads. Also in wound healing, its biodegradability plays an exclusive role of wearing away after the wound heals.
Energy Reserves of Life
Among all the classes of organic compounds, carbohydrates are the most abundant one in cells of living organisms. The basic energy yielding process of life, photosynthesis will yield carbohydrates as the products taking in carbon dioxide, light energy from the sun and the photosynthetic pigment chlorophyll. Water + Carbondioxide + energy
photosynthesis ⎯⎯⎯⎯ → ⎯
carbohydrates + oxygen
The carbohydrates serve as a major source of metabolic energy, both for plants and animals. They supply the essential nutrients in the form of sugars and starches. Excluding their nutritional role, carbohydrates also form the structural components of cellulose, which is the major portion of primary cell walls of green plants. Cellulose is a strong fiber. It cannot be digestible by humans. They are normally removed from the body along with the feces, often stated as ‘dietary fibers’ or ‘roughage’.
The important nucleic acids of RNA and DNA contain carbohydrates as one of their three essential constituents.
In energy transduction process, carbohydrates play an inevitable role by forming structural components of the compound Adenosine triphosphate (ATP) which is the energy currency of the cell.
Basic Metabolic Functions
Our body needs a regular supply of fuel to carry out daily activities and exercises. The major supply of this energy comes from carbohydrates and fats. Carbohydrates serve as a source of fuel and energy whenever the body requires. In humans, carbohydrates are mainly stored as ‘glycogen’ which are the long chain polymeric units inside the liver and skeletal muscles. After the metabolic activities, the carbohydrates are digested and broken down into glucose or the blood sugar. This can be used afterwards in case of necessity or stored as energy. Glycogen is the storage form of glucose in liver and muscles, when the glucose is not of immediate use. Carbohydrates form an important constituent of our diet. Our bodies need a constant supply of energy to function properly without tiredness. Deficiency of carbohydrates in the diet can cause carbohydrate deficiency diseases, fatigue, poor mental function and lack of endurance and vigor. They also regulate the proper functioning of our brain and the heart, the two vital organs of our body. Also, they play an important role in normal working of nervous, digestive and immune systems. As dietary fibres, carbohydrates are essential for the removal of unwanted waste materials and toxins from the body. This in turn assists us to prevent from diseases and also to maintain a clean intestine with proper bowel movements.
Metabolic Disorders Due to Carbohydrates Deficiency
Enzymes are the biological catalysts which are responsible for the major reactions inside the cell. Lactose intolerance is a metabolic disorder where the deficiency of lactase enzyme occurs in the gastrointestinal tract. As a result, break down of milk sugar or the lactose cannot occur and the nutrients are failed to be absorbed. This condition results in a meek indigestion to severe diarrhea. If the gene expression of glucose-6-phosphatase failed to occur, it will lead to ‘hypoglycemia’ which is a condition where enough glucose is not produced to meet the requirements of body. Accumulation of glycogen in liver and kidney leads to organomegaly, particularly massive hepatomegaly. The accumulation of fructose-1-phosphate molecules leads to an autosomal recessive fructose metabolism disorder. The reason is that the accumulated fructose-1-phosphate inhibits glycogenolysis and gluconeogenesis, resulting in severe hypoglycemia. This is followed by the ingestion of fructose. Prolonged fructose ingestion in infants will lead to ultimate hepatic failure and may be fatal. A set of metabolic disorders are inherited which involve the enzymes responsible for the synthesis and degradation of glycogen. Many a times, prominent liver involvement is present.
Insulin is an important hormone produced in the pancreas in our digestive system. The function of insulin is to convert the sugars into energy. Two conditions may lead to diabetes mellitus, either the body doesn’t have enough number of insulin molecules or all the insulin is not used up properly. This results in an increased glucose level in the blood. Diabetes is believed to be an inherited disease via genes. Though diabetes is a treatable disease, it greatly increases the risk of cardiovascular diseases and stroke. Most diabetes patients die due to some form of heart or blood vessel diseases. Two types of diabetes are there, diabetes I and II. Type II is more common and found in middle aged individuals, whereas type I normally occurs in young adults and children where the pancreas secretes less amount of insulin or not at all. In type I, the body doesn’t prepare sufficient insulin and also doesn’t use the insulin it makes effectively. This condition is termed as ‘insulin resistance’. The important threats for insulin resistance are obesity or overweight and physical inactivity which will end in cardiovascular disease. If diabetes mellitus is not treated properly, then it may cause life-threatening impediments. Hence once diabetes is diagnosed, treatment should be very strict like
controlling the amount of glucose in the blood through regular physical exercise, a carefully controlled diet, and medications. This helps us to avoid difficulties.
Points to remember:
• Monosaccharides are the simplest carbohydrates which can be represented by the empirical formula of (C – H2O) atoms. • • Based on the functional groups they possess, monosaccharides can be further classified into two types, aldoses and ketoses. Enantiomers are nonsuperimposable stereoisomers, which are indeed exact mirror images of each other. If (+) enantiomer rotates the plane polarized light for say, 10 degrees in the right direction, then the (-) enantiomer rotates the plane polarized light for the same 10 degrees to the left. • • • • • Fischer Projections was devised by Hermann Emil Fischer in 1891. Using Fischer projection, the three dimensional view of a compound with an asymmetrical carbon can be easily drawn in two dimensions. Epimers are those sugars which are having two different configurations at the single asymmetric carbon. Anomers are special types of epimers where the configuration differs only in the carbon atom (anomeric carbon) bearing hemiacetal or hemiketal group Like Fischer projections, English chemist Sir Walter N.Haworth introduced Haworth projections which are used to represent the three dimensional view of the cyclic structure of monosaccharides. • • • Structural arrangement of a particular molecule is called as ‘conformation’. Glycosidic bond is a special type of covalent chemical bond which joins two simple monosaccharides. Glycosidic bond is of two kinds, one is the alpha glycosidic bond where the bond is formed below the plane of the ring, and the other is the beta glycosidic linkage where the bond is above the plane of the ring. • • Oligosaccharides are sugars having two or more monosaccharide units combined together by means of glycosidic linkages between the adjacent atoms. Polysaccharides are macromolecules formed by the polymerization of simple monosaccharide or sugar units. E.g mannose, xylose and arabinose
where ‘n’ denotes the number of carbon
Starch is the major form of stored food reserves in cells of plants. Based on structure, it is of two types, Amylose is the unbranched structure whereas amylopectin is the branched starch.
• • • • • • • •
Glycogen is the glucose storage polymer used in animals. Liver and skeletal cells deserve the major part of glycogen in animals. Ruminants like cow have intestinal microorganisms that breakdown cellulose into monosaccharide nutrients with the help of beta-glycosidase enzymes. Next to cellulose, the abundantly found polysaccharide in nature is chitin. Chitin forms the composition of exoskeletons of many species of crustaceans like lobsters and crabs. The important nucleic acids of RNA and DNA contain carbohydrates as one of their three essential constituents. Deficiency of carbohydrates in the diet can cause carbohydrate deficiency diseases, fatigue, poor mental function and lack of endurance and vigor. Lactose intolerance is a metabolic disorder where the deficiency of lactase enzyme occurs in the gastrointestinal tract. If the gene expression of glucose-6-phosphatase failed to occur, it will lead to ‘hypoglycemia’ which is a condition where enough glucose is not produced to meet the requirements of body.
Insulin is an important hormone produced in the pancreas in our digestive system. The function of insulin is to convert the sugars into energy. Two conditions may lead to diabetes mellitus, either the body doesn’t have enough number of insulin molecules or all the insulin is not used up properly. This results in an increased glucose level in the blood.
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