Any member of a very abundant and widespread class of natural organic compounds that includes sugars, starch, and cellulose. They are commonly classified as monosaccharides (simple sugars; e.g., glucose, fructose), disaccharides (2-unit sugars; e.g., sucrose, lactose), oligosaccharides (3–10 or so sugars), and polysaccharides (large molecules with up to 10,000 monosaccharide units, including cellulose, starch, and glycogen). Green plants produce carbohydrates by photosynthesis. In most animals, carbohydrates are the quickly accessible reservoir of energy, and oxidation (see oxidation-reduction) of glucose in tissues supplies energy for metabolism. Many (but by no means all) carbohydrates have the general chemical formula Cmath.n(H2O)math.n. The carbon (C) atoms are bonded to hydrogen atoms (singlehorzbondH), hydroxyl groups (singlehorzbondOH; see functional group), and carbonyl groups (singlehorzbondCdoublehorzbondO), whose combinations, order, and geometric arrangement lead to a large number of isomers with the same chemical formula but different properties. The class is further enlarged because each isomer has various derivatives: uronic acids, sugars with an oxidized group; sugar alcohols, sugars with a reduced group; glycosides, compounds of sugars with other molecules containing a hydroxyl group; and amino sugars, sugars with an amino group (see amino acid).
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Chemically, carbohydrates are simple organic compounds that are aldehydes or ketones with many hydroxyl groups added, usually one on each carbon atom that is not part of the aldehyde or ketone functional group. The basic carbohydrate units are called monosaccharides, such as glucose, galactose, and fructose. The general stoichiometric formula of an unmodified monosaccharide is (C·H2O)n, where n is any number of three or greater; however, the use of this word does not follow this exact definition and many molecules with formulae that differ slightly from this are still called carbohydrates, and others that possess formulae agreeing with this general rule are not called carbohydrates (eg formaldehyde).
Monosaccharides can be linked together into what are called polysaccharides (or oligosaccharides) in almost limitless ways. Many carbohydrates contain one or more modified monosaccharide units that have had one or more groups replaced or removed. For example, deoxyribose, a component of DNA, is a modified version of ribose; chitin is composed of repeating units of N-acetylglucosamine, a nitrogen-containing form of glucose. The names of carbohydrates often end in the suffix -ose.
Monosaccharides are the simplest carbohydrates in that they cannot be hydrolyzed to smaller carbohydrates. The general chemical formula of an unmodified monosaccharide is (C•H2O)n, where n is any number of three or greater.
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 chiral 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.
Two joined monosaccharides are called a disaccharides 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:
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 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 two and nine 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 xenotransplanation, 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's structure 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.
Carbohydrates require less water to digest than proteins or fats and are the most common source of energy in living things. 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. However, the brain and neurons generally cannot burn fat and need glucose for energy; the body can make some glucose from a few of the amino acids in protein and also from the glycerol backbone in triglycerides. Carbohydrate contains 3.75 and proteins 4 kilocalories per gram, respectively, while fats contain 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; many monosaccharides and some disaccharides. Other carbohydrate types can be used, but only with the assistance of gut bacteria. Other animals, such as the ruminants and termites, can even process cellulose, while most animals cannot.
Based on the effects on risk of heart disease and obesity, the Institute of Medicine recommends that American and Canadian adults get between 40-65% 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).
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 which 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.
Oligo/polysaccharides are cleaved first to smaller monosaccharides by enzymes called Glycoside hydrolases. The monosaccharide units can then enter into monosaccharide catabolism. In some cases, as with humans, not all carbohydrate types are usable as the digestive and metabolic enzymes necessary are not present. For instance, neither horses nor humans nor cats can digest and use cellulose, but ruminants and termites can.