Sunday, July 25, 2010

Carbohydrates

A carbohydrate is an organic compound with the general formula Cm(H2O)n, that is, consists only of carbon, hydrogen and oxygen, with the last two in the 2:1 atom ratio. Carbohydrates can be viewed as hydrates of carbon, hence their name. Structurally however, it is more accurate to view them as polyhydroxy aldehydes and ketones.
The term is most common in biochemistry, where it is a synonym of saccharide. The carbohydrates (saccharides) are divided into four chemical groupings: monosaccharides, disaccharides, oligosaccharides, and polysaccharides. In general, the monosaccharides and disaccharides, which are smaller (lower molecular weight) carbohydrates, are commonly referred to as sugars.[1] The word saccharide comes from the Greek word σάκχαρον (sákkharon), meaning "sugar". While the scientific nomenclature of carbohydrates is complex, the names of the monosaccharides and disaccharides very often end in the suffix -ose. For example, blood sugar is the monosaccharide glucose, table sugar is the disaccharide sucrose, and milk sugar is the disaccharide lactose (see illustration).
Carbohydrates perform numerous roles in living things. Polysaccharides serve for the storage of energy (e.g., starch and glycogen) and as structural components (e.g., cellulose in plants and chitin in arthropods). The 5-carbon monosaccharide ribose is an important component of coenzymes (e.g., ATP, FAD, and NAD) and the backbone of the genetic molecule known as RNA. The related deoxyribose is a component of DNA. Saccharides and their derivatives include many other important biomolecules that play key roles in the immune system, fertilization, preventing pathogenesis, blood clotting, and development.
In food science and in many informal contexts, the term carbohydrate often means any food that is particularly rich in starch (such as cereals, bread and pasta) or sugar (such as candy, jams and desserts).
Monosaccharides
D-glucose is an aldohexose with the formula (C•H2O)6. The red atoms highlight the aldehyde group, and the blue atoms highlight the asymmetric center furthest from the aldehyde; because this -OH is on the right of the Fischer projection, this is a D sugar.
Monosaccharides are the simplest carbohydrates in that they cannot be hydrolyzed to smaller carbohydrates. They are aldehydes or ketones with two or more hydroxyl groups. The general chemical formula of an unmodified monosaccharide is (C•H2O)n, literally a "carbon hydrate." Monosaccharides are important fuel molecules as well as building blocks for nucleic acids. The smallest monosaccharides, for which n = 3, are dihydroxyacetone and D- and L-glyceraldehyde.
Classification of monosaccharides
The α and β anomers of glucose. Note the position of the hydroxyl group (red or green) on the anomeric carbon relative to the CH2OH group bound to carbon 5: they are either on the opposite sides (α), or the same side (β).
Monosaccharides are classified according to three different characteristics: the placement of its carbonyl group, the number of carbon atoms it contains, and its chiral handedness. If the carbonyl group is an aldehyde, the monosaccharide is an aldose; if the carbonyl group is a ketone, the monosaccharide is a ketose. Monosaccharides with three carbon atoms are called trioses, those with four are called tetroses, five are called pentoses, six are hexoses, and so on. [6] These two systems of classification are often combined. For example, glucose is an aldohexose (a six-carbon aldehyde), ribose is an aldopentose (a five-carbon aldehyde), and fructose is a ketohexose (a six-carbon ketone).
Each carbon atom bearing a hydroxyl group (-OH), with the exception of the first and last carbons, are asymmetric, making them stereocenters with two possible configurations each (R or S). Because of this asymmetry, a number of isomers may exist for any given monosaccharide formula. The aldohexose D-glucose, for example, has the formula (C•H2O)6, of which all but two of its six carbons atoms are stereogenic, making D-glucose one of 24 = 16 possible stereoisomers. In the case of glyceraldehyde, an aldotriose, there is one pair of possible stereoisomers, which are enantiomers and epimers. 1,3-dihydroxyacetone, the ketose corresponding to the aldose glyceraldehyde, is a symmetric molecule with no stereocenters). The assignment of D or L is made according to the orientation of the asymmetric carbon furthest from the carbonyl group: in a standard Fischer projection if the hydroxyl group is on the right the molecule is a D sugar, otherwise it is an L sugar. The "D-" and "L-" prefixes should not be confused with "d-" or "l-", which indicate the direction that the sugar rotates plane polarized light. This usage of "d-" and "l-" is no longer followed in carbohydrate chemistry.
The aldehyde or ketone group of a straight-chain monosaccharide will react reversibly with a hydroxyl group on a different carbon atom to form a hemiacetal or hemiketal, forming a heterocyclic ring with an oxygen bridge between two carbon atoms. Rings with five and six atoms are called furanose and pyranose forms, respectively, and exist in equilibrium with the straight-chain form.
During the conversion from straight-chain form to cyclic form, the carbon atom containing the carbonyl oxygen, called the anomeric carbon, becomes a stereogenic center with two possible configurations: The oxygen atom may take a position either above or below the plane of the ring. The resulting possible pair of stereoisomers are called anomers. In the α anomer, the -OH substituent on the anomeric carbon rests on the opposite side (trans) of the ring from the CH2OH side branch. The alternative form, in which the CH2OH substituent and the anomeric hydroxyl are on the same side (cis) of the plane of the ring, is called the β anomer. You can remember that the β anomer is cis by the mnemonic, "It's always better to βe up". Because the ring and straight-chain forms readily interconvert, both anomers exist in equilibrium.[8] In a Fischer Projection, the α anomer is represented with the anomeric hydroxyl group trans to the CH2OH and cis in the β anomer.
Use in living organisms
Monosaccharides are the major source of fuel for metabolism, being used both as an energy source (glucose being the most important in nature) and in biosynthesis. When monosaccharides are not immediately needed by many cells they are often converted to more space efficient forms, often polysaccharides. In many animals, including humans, this storage form is glycogen, especially in liver and muscle cells. In plants, starch is used for the same purpose.
Disaccharides
Sucrose, also known as table sugar, is a common disaccharide. It is composed of two monosaccharides: D-glucose (left) and D-fructose (right).
Two joined monosaccharides are called a disaccharide and these are the simplest polysaccharides. Examples include sucrose and lactose. They are composed of two monosaccharide units bound together by a covalent bond known as a glycosidic linkage formed via a dehydration reaction, resulting in the loss of a hydrogen atom from one monosaccharide and a hydroxyl group from the other. The formula of unmodified disaccharides is C12H22O11. Although there are numerous kinds of disaccharides, a handful of disaccharides are particularly notable.
Sucrose, pictured to the right, is the most abundant disaccharide, and the main form in which carbohydrates are transported in plants. It is composed of one D-glucose molecule and one D-fructose molecule. The systematic name for sucrose, O-α-D-glucopyranosyl-(1→2)-D-fructofuranoside, indicates four things:
* Its monosaccharides: glucose and fructose
* Their ring types: glucose is a pyranose, and fructose is a furanose
* How they are linked together: the oxygen on carbon number 1 (C1) of α-D-glucose is linked to the C2 of D-fructose.
* The -oside suffix indicates that the anomeric carbon of both monosaccharides participates in the glycosidic bond.

Lactose, a disaccharide composed of one D-galactose molecule and one D-glucose molecule, occurs naturally in mammalian milk. The systematic name for lactose is O-β-D-galactopyranosyl-(1→4)-D-glucopyranose. Other notable disaccharides include maltose (two D-glucoses linked α-1,4) and cellulobiose (two D-glucoses linked β-1,4).
Oligosaccharides and polysaccharides
Amylose is a linear polymer of glucose mainly linked with α(1→4) bonds. It can be made of several thousands of glucose units. It is one of the two components of starch, the other being amylopectin.
Oligosaccharides and polysaccharides are composed of longer chains of monosaccharide units bound together by glycosidic bonds. The distinction between the two is based upon the number of monosaccharide units present in the chain. Oligosaccharides typically contain between three and ten monosaccharide units, and polysaccharides contain greater than ten monosaccharide units. Definitions of how large a carbohydrate must be to fall into each category vary according to personal opinion. Examples of oligosaccharides include the disaccharides mentioned above, the trisaccharide raffinose and the tetrasaccharide stachyose.
Oligosaccharides are found as a common form of protein posttranslational modification. Such posttranslational modifications include the Lewis and ABO oligosaccharides responsible for blood group classifications and so of tissue incompatibilities, the alpha-Gal epitope responsible for hyperacute rejection in xenotransplantation, and O-GlcNAc modifications.
Polysaccharides represent an important class of biological polymers. Their function in living organisms is usually either structure- or storage-related. Starch (a polymer of glucose) is used as a storage polysaccharide in plants, being found in the form of both amylose and the branched amylopectin. In animals, the structurally similar glucose polymer is the more densely branched glycogen, sometimes called 'animal starch'. Glycogen's properties allow it to be metabolized more quickly, which suits the active lives of moving animals.
Cellulose and chitin are examples of structural polysaccharides. Cellulose is used in the cell walls of plants and other organisms, and is claimed to be the most abundant organic molecule on earth. It has many uses such as a significant role in the paper and textile industries, and is used as a feedstock for the production of rayon (via the viscose process), cellulose acetate, celluloid, and nitrocellulose. Chitin has a similar structure, but has nitrogen-containing side branches, increasing its strength. It is found in arthropod exoskeletons and in the cell walls of some fungi. It also has multiple uses, including surgical threads.
Other polysaccharides include callose or laminarin, chrysolaminarin, xylan, arabinoxylan, mannan, fucoidan, and galactomannan.
Nutrition
Grain products: rich sources of complex and simple carbohydrates
Foods high in simple carbohydrates include fruits, sweets and soft drinks. Foods high in complex carbohydrates include breads, pastas, beans, potatoes, bran, rice, and cereals. The most common complex carbohydrate in these foods is starch. Carbohydrates are the most common source of energy in living organisms. Proteins and fat are necessary building components for body tissue and cells, and are also a source of energy for most organisms.
Carbohydrates are not essential nutrients in humans: the body can obtain all its energy from protein and fats[10][11]. The brain and neurons generally cannot burn fat for energy, but can use glucose or ketones; the body can also synthesize some glucose from a few of the amino acids in protein and also from the glycerol backbone in triglycerides. Carbohydrate contains 15.8 kilojoules (3.75 kilocalories)[citation needed] and proteins 16.8 kilojoules (4 kilocalories) per gram, while fats contain 37.8 kilojoules (9 kilocalories) per gram. In the case of protein, this is somewhat misleading as only some amino acids are usable for fuel. Likewise, in humans, only some carbohydrates are usable for fuel, as in many monosaccharides and some disaccharides. Other carbohydrate types can be used, but only with the assistance of gut bacteria. Ruminants and termites can even process cellulose, which is indigestible to humans.
Based on the effects on risk of heart disease and obesity, the Institute of Medicine recommends that American and Canadian adults get between 45–65% of dietary energy from carbohydrates. The Food and Agriculture Organization and World Health Organization jointly recommend that national dietary guidelines set a goal of 55–75% of total energy from carbohydrates, but only 10% directly from sugars (their term for simple carbohydrates).



Classification
For dietary purposes, carbohydrates can be classified as simple (monosaccharides and disaccharides) or complex (oligosaccharides and polysaccharides). The term complex carbohydrate was first used in the U.S. Senate Select Committee on Nutrition and Human Needs publication Dietary Goals for the United States (1977), where it denoted "fruit, vegetables and whole-grains".Dietary guidelines generally recommend that complex carbohydrates, and such nutrient-rich simple carbohydrate sources such as fruit (glucose or fructose) and dairy products (lactose) make up the bulk of carbohydrate consumption. This excludes such sources of simple sugars as candy and sugary drinks.
The glycemic index and glycemic load concepts have been developed to characterize food behavior during human digestion. They rank carbohydrate-rich foods based on the rapidity of their effect on blood glucose levels. The insulin index is a similar, more recent classification method that ranks foods based on their effects on blood insulin levels, which are caused by glucose (or starch) and some amino acids in food. Glycemic index is a measure of how quickly food glucose is absorbed, while glycemic load is a measure of the total absorbable glucose in foods.

Reference: http://en.wikipedia.org/wiki/Carbohydrate

Wednesday, July 21, 2010

Carbohydrates

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Saturday, July 10, 2010

Acids and Bases

Acids and Bases
An Introduction

by Anthony Carpi, Ph.D.

For thousands of years people have known that vinegar, lemon juice and many other foods taste sour. However, it was not until a few hundred years ago that it was discovered why these things taste sour - because they are all acids. The term acid, in fact, comes from the Latin term acere, which means "sour". While there are many slightly different definitions of acids and bases, in this lesson we will introduce the fundamentals of acid/base chemistry.

In the seventeenth century, the Irish writer and amateur chemist Robert Boyle first labeled substances as either acids or bases (he called bases alkalies) according to the following characteristics:

* Acids taste sour, are corrosive to metals, change litmus (a dye extracted from lichens) red, and become less acidic when mixed with bases.
* Bases feel slippery, change litmus blue, and become less basic when mixed with acids.

While Boyle and others tried to explain why acids and bases behave the way they do, the first reasonable definition of acids and bases would not be proposed until 200 years later.

In the late 1800s, the Swedish scientist Svante Arrhenius proposed that water can dissolve many compounds by separating them into their individual ions. Arrhenius suggested that acids are compounds that contain hydrogen and can dissolve in water to release hydrogen ions into solution. For example, hydrochloric acid (HCl) dissolves in water as follows:
HCl H2O
H+(aq) + Cl-(aq)

Arrhenius defined bases as substances that dissolve in water to release hydroxide ions (OH-) into solution. For example, a typical base according to the Arrhenius definition is sodium hydroxide (NaOH):
NaOH H2O
Na+(aq) + OH-(aq)

The Arrhenius definition of acids and bases explains a number of things. Arrhenius's theory explains why all acids have similar properties to each other (and, conversely, why all bases are similar): because all acids release H+ into solution (and all bases release OH-). The Arrhenius definition also explains Boyle's observation that acids and bases counteract each other. This idea, that a base can make an acid weaker, and vice versa, is called neutralization.

Neutralization: As you can see from the equations, acids release H+ into solution and bases release OH-. If we were to mix an acid and base together, the H+ ion would combine with the OH- ion to make the molecule H2O, or plain water:
H+(aq) + OH-(aq) H2O

The neutralization reaction of an acid with a base will always produce water and a salt, as shown below:
Acid Base Water Salt
HCl + NaOH H2O + NaCl
HBr + KOH H2O + KBr

Though Arrhenius helped explain the fundamentals of acid/base chemistry, unfortunately his theories have limits. For example, the Arrhenius definition does not explain why some substances, such as common baking soda (NaHCO3), can act like a base even though they do not contain hydroxide ions.

In 1923, the Danish scientist Johannes Brønsted and the Englishman Thomas Lowry published independent yet similar papers that refined Arrhenius' theory. In Brønsted's words, "... acids and bases are substances that are capable of splitting off or taking up hydrogen ions, respectively." The Brønsted-Lowry definition broadened the Arrhenius concept of acids and bases.

The Brønsted-Lowry definition of acids is very similar to the Arrhenius definition, any substance that can donate a hydrogen ion is an acid (under the Brønsted definition, acids are often referred to as proton donors because an H+ ion, hydrogen minus its electron, is simply a proton).

The Brønsted definition of bases is, however, quite different from the Arrhenius definition. The Brønsted base is defined as any substance that can accept a hydrogen ion. In essence, a base is the opposite of an acid. NaOH and KOH, as we saw above, would still be considered bases because they can accept an H+ from an acid to form water. However, the Brønsted-Lowry definition also explains why substances that do not contain OH- can act like bases. Baking soda (NaHCO3), for example, acts like a base by accepting a hydrogen ion from an acid as illustrated below:
Acid Base Salt
HCl + NaHCO3 H2CO3 + NaCl
In this example, the carbonic acid formed (H2CO3) undergoes rapid decomposition to water and gaseous carbon dioxide, and so the solution bubbles as CO2 gas is released.

pH
Under the Brønsted-Lowry definition, both acids and bases are related to the concentration of hydrogen ions present. Acids increase the concentration of hydrogen ions, while bases decrease the concentration of hydrogen ions (by accepting them). The acidity or basicity of something, therefore, can be measured by its hydrogen ion concentration.

In 1909, the Danish biochemist Sören Sörensen invented the pH scale for measuring acidity. The pH scale is described by the formula:

pH = -log [H+] Note: concentration is commonly abbreviated by using square brackets, thus [H+] = hydrogen ion concentration. When measuring pH, [H+] is in units of moles of H+ per liter of solution.

For example, a solution with [H+] = 1 x 10-7 moles/liter has a pH equal to 7 (a simpler way to think about pH is that it equals the exponent on the H+ concentration, ignoring the minus sign). The pH scale ranges from 0 to 14. Substances with a pH between 0 and less than 7 are acids (pH and [H+] are inversely related - lower pH means higher [H+]). Substances with a pH greater than 7 and up to 14 are bases (higher pH means lower [H+]). Right in the middle, at pH = 7, are neutral substances, for example, pure water. The relationship between [H+] and pH is shown in the table below alongside some common examples of acids and bases in everyday life.
[H+] pH Example
Acids 1 X 100 0 HCl
1 x 10-1 1 Stomach acid
1 x 10-2 2 Lemon juice
1 x 10-3 3 Vinegar
1 x 10-4 4 Soda
1 x 10-5 5 Rainwater
1 x 10-6 6 Milk
Neutral 1 x 10-7 7 Pure water
Bases 1 x 10-8 8 Egg whites
1 x 10-9 9 Baking soda
1 x 10-10 10 Tums® antacid
1 x 10-11 11 Ammonia
1 x 10-12 12 Mineral lime - Ca(OH)2
1 x 10-13 13 Drano®
1 x 10-14 14 NaOH

Reference:http://www.visionlearning.com/library/module_viewer.php?mid=58