Carbohydrate Chemistry, Chemistry tutorial


Carbohydrates are the richest organic compounds in the plant world. They act as storehouses of the chemical energy (that is, glucose, starch and glycogen); are the components of supportive structures in plants (that is, cellulose), crustacean shells (that is, chitin) and connective tissues in animals (that is, acidic polysaccharides); and are necessary components of nucleic acids (D-ribose and 2-deoxy-D-ribose). The carbohydrates prepare approximately three fourths of the dry weight of plants. Animals (comprising humans) get their carbohydrates via eating plants; however they don't store much of what they use. Less than 1% of the body weight of animals is prepared of carbohydrates.

Carbohydrates are as well the richest class of organic compounds found in the living organisms. They originate as products of photosynthesis, an endothermic reductive condensation of carbon-dioxide need light energy and the pigment chlorophyll.

The name carbohydrate signifies hydrate of carbon and derives from the formula Cn(H2O)m. Following are the two illustrations of carbohydrates having molecular formulas which can be written instead as hydrates of carbon.

Glucose (blood sugar): C6H12O6, or alternatively C6(H2O)6

Sucrose (table sugar): C12H22O11, or alternatively C12(H2O)11

Not all carbohydrates, though, encompass this general formula. Some have too few oxygen atoms to fit this formula, and some others have too many oxygen. Some as well have nitrogen. The word carbohydrate has become so firmly rooted in the chemical nomenclature that, however not fully accurate, it continues as the name for this class of compounds.

At molecular level, most of the carbohydrates are polyhydroxyaldehydes, polyhydroxyketones, or compounds which result either of such after hydrolysis. Thus, the chemistry of carbohydrates is necessarily the chemistry of hydroxyl groups and carbonyl groups, and of the acetal bonds made between such two functional groups.

Classification and nomenclature:

However a number of categorization schemes have been devised for carbohydrates, some of the main four groups are: monosaccharides, disaccharides, oligosaccharides and polysaccharides - used here is among the most general.

1) Monosaccharides:

Most of the monosaccharides, or simple sugars, are found in grapes, other fruits and honey. However they can encompass from three to nine carbon atoms, the most common representatives comprise of five or six joined altogether to form a chainlike molecule. Three of the most significant simple sugars - glucose (as well termed as dextrose, grape sugar and corn sugar), fructose (that is, fruit sugar), and galactose encompass the similar molecular formula, (C6H12O6), however, due to their atoms have various structural arrangements, the sugars have diverse characteristics; that is, they are isomers. Slight changes in the structural arrangements are detectable via living things and affect the biological importance of isomeric compounds. It is known, for illustration that the degree of sweetness of different sugars varies according to the arrangement of the hydroxyl groups (-OH) which compose part of the molecular structure. A direct correlation which might exist between taste and any specific structural arrangement, though, has not yet been established; that is, it is not yet possible to forecast the taste of a sugar by knowing its particular structural arrangement. The energy in the chemical bonds of glucose indirectly supplies most living things having a main part of the energy which is essential for them to carry on their activities. Galactose, which is hardly ever found as a simple sugar, is generally combined by other simple sugars in order to form larger molecules.

2) Disaccharides:

Two molecules of a simple sugar which are linked to one other form a disaccharide, or double sugar. The disaccharide sucrose, or table sugar, comprises of one molecule of glucose and one molecule of fructose; the most well-known sources of sucrose are sugar beets and cane sugar. Milk sugar, or lactose and maltose are as well disaccharides. Prior to the energy in disaccharides can be used by living things, the molecules should be broken down to their particular monosaccharides.

3) Oligosaccharides:

Oligosaccharides that comprise of three to six monosaccharide units are somewhat infrequently found in the natural sources; however a few plant derivatives have been recognized.

4) Polysaccharides:

Polysaccharides (the word signifies many sugars) represent most of the structural and energy-reserve carbohydrates found in the nature. Large molecules which might comprise of as many as 10,000 monosaccharide units linked altogether, polysaccharides differ considerably in size, in structural complexity and in the sugar content; several hundred distinct kinds have therefore far been recognized. Cellulose, the main structural component of plants, is the complex polysaccharide including most of the glucose units linked altogether; it is the most general polysaccharide. The starch found in plants and the glycogen found in animals as well is complex glucose polysaccharides. Starch (that is, from the Old English word stercan, meaning 'to stiffen') is mostly found in roots, seeds and stems, where it is stored as an available energy source for plants. Plant starch might be processed into these foods as bread, or it might be used directly - as in potatoes, for example. Glycogen that comprises of branching chains of glucose molecules is prepared in the liver and muscles of higher animals and is stored as the energy source.

Biological significance:

The significance of carbohydrates to living things can only just be overemphasized. The energy stores of most plants and animals are both carbohydrate and lipid in nature; carbohydrates are usually available as an immediate energy source, while lipids act as a long-term energy resource and tend to be used at a slower rate. Glucose, the prevalent uncombined, or free, sugar circulating in the blood of higher animals, is necessary or vital to cell function. The appropriate regulation of glucose metabolism is of paramount significance to survival.

Role in the Biosphere:

The important procedure in the biosphere, the part of the Earth in which life can take place, that has permitted the evolution of life as it now exists is the transformation by green plants of carbon-dioxide from the atmosphere into carbohydrates, employing light energy from the Sun. This procedure, termed as photosynthesis, yields in both the discharge of oxygen gas into the atmosphere and the conversion of light energy to the chemical energy of carbohydrates. The energy stored via plants throughout the formation of carbohydrates is employed by animals to carry out mechanical work and to carry out biosynthetic activities.

Role in Human Nutrition:

The net caloric, or energy, necessity for an individual based on age, occupation and other factors however usually ranges between 2,000 and 4,000 calories per 24-hour period (that is, one calorie, as this word is employed in nutrition, is the amount of heat required to increase the temperature of 1,000 grams of water from 15 to 16 °C [59 to 61 °F]; in other contexts this quantity of heat is called the kilocalorie). Carbohydrate that can be used by humans produces four calories per gram as opposed to nine calories per gram of fat and four per gram of protein. In regions of the world where nutrition is unimportant, a high proportion (around one to two pounds) of an individual's daily energy need might be supplied by carbohydrate, with most of the remainder coming from the variety of fat sources.

However carbohydrates might compose as much as 80% of the net caloric intake in the human diet, for a given diet, the proportion of starch to net carbohydrate is quite variable, based on the prevailing customs. In East Asia and in regions of Africa, for illustration, where rice or tubers like manioc give a main food source, starch might account for as much as 80 % of the total carbohydrate intake. In a usual Western diet, 33 to 50 % of the caloric intake is in the form of carbohydrate. Around half (that is, 17 to 25 %) is symbolized by starch; the other third by table sugar (that is, sucrose) and milk sugar (that is, lactose); and smaller percentages via monosaccharides like glucose and fructose that are common in fruits, syrups, honey and some vegetables like artichokes, onions and sugar beets. The small remainder comprises of bulk or indigestible carbohydrate that mainly comprises the cellulosic outer covering of seeds and the stalks and leaves of vegetables.

Role in energy storage:

Starches, the main plant-energy-reserve polysaccharides employed by humans, are stored in the plants in the form of almost spherical granules that differ in diameter from around three to 100 micrometers (around 0.0001 to 0.004 inch). Most of the plant starches comprise of a mixture of two components: Amylose and amylopectin. The glucose molecules composing amylose encompass a straight-chain, or linear, structure. Amylopectin consists of a branched-chain structure and is a fairly more compact molecule. Several thousand glucose units might be present in a single starch molecule.

Role in plant and animal structure:

As starches and glycogen represent the main reserve polysaccharides of living things, most of the carbohydrate found in nature takes place as structural components in the cell walls of plants. Carbohydrates in the plant cell walls usually comprise of some different layers, one of which includes a higher concentration of cellulose than the others. The physical and chemical properties of cellulose are strikingly dissimilar from those of the Amylose component of starch.

In most of the plants, the cell wall is around 0.5 micrometer thick and includes a mixture of cellulose, pentose-having polysaccharides (that is, pentosans), and an inert (chemically unreactive) plastic-like material known as lignin. The amounts of cellulose and pentosan might differ; most of the plants enclose between 40 and 60 % cellulose, however higher amounts are present in the cotton fibre.

Polysaccharides as well function as main structural components in animals. Chitin that is identical to cellulose is found in the insects and other arthropods. The other complex polysaccharides predominate in the structural tissues of the higher animals.

Stereoisomerism of carbohydrates:

Isomers are the compounds having similar molecular formulas. Isomers can be classified into the two different groups of constitutional isomers or stereoisomer.

Constitutional isomers encompass the similar molecular formula however a different molecular framework (various bonding constitution). As constitutional isomers encompass different bonding constitutions, they are dissimilar molecules. This signifies that constitutional isomers encompass various physical and chemical properties. Ethanol CH3CH2OH and dimethyl ether CH3OCH3 are constitutional isomers. Both encompass the similar molecular formula (C2H6O) however differ in how the atoms are linked.

Stereoisomers are the molecules having similar atoms bonded identically however the bonded atoms are oriented differently in space. That is to state, they encompass similar bonding constitutions however differ in how the atoms are oriented in the space around the atoms to which they are bonded.

The Stereoisomers can be further separated into the two groups of diastereomers and enantiomers. One kind of diastereomers (or geometric stereoisomer) varies by 'cis' and 'trans' orientations.

Enantiomers are the class of stereoisomer associated similar to an object and its mirror image. Enantiomers vary in their 'handedness' as the left hand and right hand are connected. Enantiomers are a pair of mirror image molecules which can't be superimposed on one other.   Superimposed proposes that the two mirror image molecules can be mentally merged to one object as they are brought altogether.

There are two well-known 'handed' biologically significant molecules. The D-sugars and L- amino acids. The designations of D- and L- refer to how the pair of enantiomers varies in their bonding configurations. In biochemistry, D is the symbol employed as a prefix to point out the spatial configuration of some organic compounds having asymmetric carbon atoms. It is employed if an organic compound consists of a configuration regarding an asymmetric carbon atom (that is, Chiral center) analogous to that of D-glyceraldehyde (that is, the randomly selected standard), in which the hydroxy (OH) functional group is on the right side of the asymmetric carbon atom.

The word 'Chirality' signifies to the 'handedness' of a molecule.  Chiral molecules encompass a chiral center and such pair of molecules can't be superimposed. The chiral center is an atom having four different substituents. The carbon atom which consists of four different groups bonded to it is termed as asymmetric carbon or a chiral carbon. On the other hand, achiral molecules (that is, molecules 'devoid of handedness') can be superimposed.

Enantiomers are similar in most physical and chemical properties like: boiling point, melting point, density and chemical reactions usual for the functional groups present in the molecule.

Though, there are two physical properties that permit discernment of chirality:

1) The Chiral molecules differ in their interaction by plane polarized light. (Chiral molecules are at times termed as optical isomers.) The polarimeter is a device which lets plane polarized light to pass via aqueous solution of the molecule. The (+) isomer rotates plane polarized light clockwise. The (-) isomer rotates plane polarized light counter-clockwise. The achiral molecules don't rotate polarized light in either direction. Racemic mixtures have equivalent mix of (+) and (-) isomers. Racemic mixtures represent NO rotation of polarized light.

2) Chiral as well molecules differ in their interaction by other chiral compounds. Chiral molecules particularly recognize other chiral molecules. For illustration, L-amino acid protein   enzyme (that is, chiral molecule)

Reactions of Carbohydrates:

The enzymes which break down polysaccharides are particular to the kind of linkage in the polysaccharide.  The enzymes, cellulase, which hydrolyze the beta linkages in cellulose, are dissimilar from the enzyme, amylase which hydrolyzes alpha linkages. The beta linkages are not broken down via the enzymes that people have and as a result, cellulose doesn't supply glucose in our diets. This is the case as most of the organisms simply don't have the cellulase enzyme in their bodies; however they do encompass the amylase enzyme.

The Benedict's test employed by disaccharides to differentiate between sucrose, maltose and lactose. The Lactose and maltose react to change the Benedict Reagent from a clear blue solution to a cloudy rust or brown solution, however sucrose doesn't react.

The Iodine test employed to check for the presents of starch, particularly Amylose. The Amylose compound will turn the iodine solution black.

Fermentation will take place whenever an enzyme found in yeast reacts by sucrose or maltose to prepare ethanol and carbon-dioxide gas.  No fermentation will take place with lactose. Yeast doesn't comprise that enzyme.

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