which among other properties contains carbon, hydrogen, and oxygen, mostly in a ratio of 1:2:1 (generalized formula CnH2nOn, where n is at least 3). Glucose, one of the most important carbohydrates, is an example of a monosaccharide. So is fructose, the sugar that gives fruits their sweet taste. Some carbohydrates (especially after condensation to oligo- and polysaccharides) contain less carbon relative to H and O, which still are present in 2:1 (H:O) ratio. Monosaccharides can be grouped into aldoses (having an aldehyde group at the end of the chain, e. g. glucose) and ketoses (having a keto group in their chain; e. g. fructose). Both aldoses and ketoses occur in an equilibrium between the open-chain forms and (starting with chain lengths of C4) cyclic forms. These are generated by bond formation between one of the hydroxy groups of the sugar chain with the carbon of the aldehyde or keto group in a semiacetal bond. This leads to saturated five-membered (in furanoses) or six-membered (in pyranoses) heterocyclic rings containing one O as heteroatom.Two monosaccharides can be joined together using dehydration synthesis, in which a hydrogen atom is removed from the end of one molecule and a hydroxyl group (—OH) is removed from the other; the remaining residues are then attached at the sites from which the atoms were removed. The H—OH or H2O is then released as a molecule of water, hence the term dehydration. The new molecule, consisting of two monosaccharides, is called a disaccharide and is conjoined together by a glycosidic or ether bond. The reverse reaction can also occur, using a molecule of water to split up a disaccharide and break the glycosidic bond; this is termed hydrolysis. The most well-known disaccharide is sucrose, ordinary sugar (in scientific contexts, called table sugar or cane sugar to differentiate it from other sugars). Sucrose consists of a glucose molecule and a fructose molecule joined together. Another important disaccharide is lactose, consisting of a glucose molecule and a galactose molecule. As most humans age, the production of lactase, the enzyme that hydrolyzes lactose back into glucose and galactose, typically decreases. This results in lactase deficiency, also called lactose intolerance.
Sugar polymers are characterised by having reducing or non-reducing ends. A reducing end of a carbohydrate is a carbon atom which can be in equilibrium with the open-chain aldehyde or keto form. If the joining of monomers takes place at such a carbon atom, the free hydroxy group of the pyranose or furanose form is exchanged with an OH-side chain of another sugar, yielding a full acetal. This prevents opening of the chain to the aldehyde or keto form and renders the modified residue non-reducing. Lactose contains a reducing end at its glucose moiety, whereas the galactose moiety form a full acetal with the C4-OH group of glucose. Saccharose does not have a reducing end because of full acetal formation between the aldehyde carbon of glucose (C1) and the keto carbon of fructose (C2).
When a few (around three to six) monosaccharides are joined together, it is called an oligosaccharide (oligo- meaning "few"). These molecules tend to be used as markers and signals, as well as having some other uses.
Many monosaccharides joined together make a polysaccharide. They can be joined together in one long linear chain, or they may be branched. Two of the most common polysaccharides are cellulose and glycogen, both consisting of repeating glucose monomers. Cellulose is made by plants and is an important structural component of their cell walls. Humans can neither manufacture nor digest it. Glycogen, on the other hand, is an animal carbohydrate; humans use it as a form of energy storage.
Glucose is the major energy source in most life forms; a number of catabolic pathways converge on glucose. For instance, polysaccharides are broken down into their monomers (glycogen phosphorylase removes glucose residues from glycogen). Disaccharides like lactose or sucrose are cleaved into their two component monosaccharides. Glucose is mainly metabolized by a very important and ancient ten-step pathway called glycolysis, the net result of which is to break down one molecule of glucose into two molecules of pyruvate; this also produces a net two molecules of ATP, the energy currency of cells, along with two reducing equivalents in the form of converting NAD+ to NADH. This does not require oxygen; if no oxygen is available (or the cell cannot use oxygen), the NAD is restored by converting the pyruvate to lactate (e. g. in humans) or to ethanol plus carbon dioxide (e. g. in yeast). Other monosaccharides like galactose and fructose can be converted into intermediates of the glycolytic pathway. In aerobic cells with sufficient oxygen, like most human cells, the pyruvate is further metabolized. It is irreversibly converted to acetyl-CoA, giving off one carbon atom as the waste product carbon dioxide, generating another reducing equivalent as NADH. The two molecules acetyl-CoA (from one molecule of glucose) then enter the citric acid cycle, producing two more molecules of ATP, six more NADH molecules and two reduced (ubi)quinones (via FADH2 as enzyme-bound cofactor), and releasing the remaining carbon atoms as carbon dioxide. The produced NADH and quinol molecules then feed into the enzyme complexes of the respiratory chain, an electron transport system transferring the electrons ultimately to oxygen and conserving the released energy in the form of a proton gradient over a membrane (inner mitochondrial membrane in eukaryotes). Thereby, oxygen is reduced to water and the original electron acceptors NAD+ and quinone are regenerated. This is why humans breathe in oxygen and breathe out carbon dioxide. The energy released from transferring the electrons from high-energy states in NADH and quinol is conserved first as proton gradient and converted to ATP via ATP synthase. This generates an additional 28 molecules of ATP (24 from the 8 NADH + 4 from the 2 quinols), totaling to 32 molecules of ATP conserved per degraded glucose (two from glycolysis + two from the citrate cycle). It is clear that using oxygen to completely oxidize glucose provides an organism with far more energy than any oxygen-independent metabolic feature, and this is thought to be the reason why complex life appeared only after Earth's atmosphere accumulated large amounts of oxygen.
In vertebrates, vigorously contracting skeletal muscles (during weightlifting or sprinting, for example) do not receive enough oxygen to meet the energy demand, and so they shift to anaerobic metabolism, converting glucose to lactate (lactic acid). The liver regenerates the glucose, using a process called gluconeogenesis. This process is not quite the opposite of glycolysis, and actually requires three times the amount of energy gained from glycolysis (six molecules of ATP are used, compared to the two gained in glycolysis). Analogous to the above reactions, the glucose produced can then undergo glycolysis in tissues that need energy, be stored as glycogen (or starch in plants), or be converted to other monosaccharides or joined into di- or oligosaccharides.
Carbohydrates are molecules that contain oxygen, hydrogen, and carbon atoms. They may also contain other elements such as sulfur or nitrogen, but these are usually minor components. They consist of monosaccharide sugars, of varying chain lengths, that have the general chemical formula Cn(H2O)n or are derivatives of such.The smallest value for n is 3. A 3-carbon sugar is referred to as a triose, whereas a 6-carbon sugar is called a hexose (see monosaccharides below). Certain carbohydrates are important for storing and transporting energy in most organisms, including plants and animals, and are major structural elements in many organisms (eg cellulose in plants). In addition they play major roles in cell to cell communication, the immune system, fertilization, pathogenesis, blood clotting, and development. Carbohydrates can be classified by the number of constituent sugar units: monosaccharides (such as glucose and fructose), disaccharides (such as sucrose and lactose), oligosaccharides, and polysaccharides (such as starch, glycogen, and cellulose).
Glucose as a straight-chain carbohydrate (Fischer projection)
Fructose (Fischer projection)
Pure carbohydrates contain carbon, hydrogen, and oxygen atoms, in a 1:2:1 molar ratio, giving the general formula Cn(H2O)n. (This applies only to monosaccharides, see below, although all carbohydrates have the more general formula Cn(H2O)m.) However, many important carbohydrates deviate from this, such as deoxyribose and glycerol. Sometimes compounds containing other elements are also counted as carbohydrates (e.g. glucosamine and chitin, which contain nitrogen).
The simplest carbohydrates are monosaccharides, which are small straight-chain aldehydes and ketones with many hydroxyl groups added, usually one on each carbon except the functional group. Other carbohydrates are composed of monosaccharide units and break down under hydrolysis. These may be classified as disaccharides, oligosaccharides, or polysaccharides, depending on whether they have two, several, or many monosaccharide units.
Monosaccharides
Monosaccharides may be divided into aldoses, which have an aldehyde group on the first carbon atom, and ketoses, which typically have a ketone group on the second. They may also be divided into trioses, tetroses, pentoses, hexoses,and many more. This all depends on how many carbon atoms they contain. For instance, glucose is an aldohexose, fructose a ketohexose, and ribose an aldopentose.
Further, each carbon atom that supports a hydroxyl group (except for the first and last) is a stereogenic centre, allowing a number of different enantiomers and stereoisomers for carbohydrates with the same basic structure. For instance, galactose is an aldohexose but has different properties from glucose because the atoms are arranged differently.
A heterocyclic form of ribose (Haworth projection)
The straight-chain structure described here is only one of the forms a monosaccharide may take. The aldehyde or ketone group may react with a hydroxyl group on a different carbon atom to form a hemiacetal or hemiketal, in which case there is an oxygen bridge between the two carbon atoms, forming a heterocyclic ring. Rings with five and six atoms are called furanose and pyranose forms and exist in equilibrium with the straight-chain form.
It should be noted that the ring form has one more stereogenic centre than the straight-chain form, and so has both an alpha and a beta form, which interconvert in equilibrium. However, the carbohydrate may further react with an alcohol to form an acetal or ketal, in which case the two forms become distinct. This is the basic type of link between the monosaccharide units of larger carbohydrates. Excessive consumption may cause obesity.
An aldose is a monosaccharide (a certain type of sugar) containing one aldehyde group per molecule and having a chemical formula of the form CnH2nOn (n>=3).
Triose: glyceraldehyde
Tetroses: erythrose, threose
Pentoses: ribose, arabinose, xylose, lyxose
Hexoses: allose, altrose, glucose, mannose, gulose, idose, galactose, talose
With only 3 carbon atoms, glyceraldehyde is the simplest of all aldoses.
Aldoses isomerize to ketoses in the Lobry-de Bruyn-van Ekenstein transformation
An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom which is bonded to a hydrogen atom and double-bonded to an oxygen atom (chemical formula -CHO), is called the aldehyde group. The aldehyde group is also called the formyl or methanoyl group.
The word aldehyde seems to have arisen from alcohol dehydrogenated. In the past, aldehydes were sometimes named after the corresponding alcohols, for example vinous aldehyde for acetaldehyde. (Vinous is from Latin vinum = wine, the traditional source of ethanol; compare vinyl.)
The aldehyde group is polar. Oxygen, being more electronegative, pulls the electrons in the carbon-oxygen bond towards itself, thus creating an electron deficiency at the carbon atom.
Disaccharides
Disaccharides are composed of two monosaccharide units bound together by a covalent glycosidic bond. The binding between the two sugars results in the loss of a hydrogen atom (H) from one molecule and a hydroxyl group (OH) from the other.
The most common disaccharides are sucrose (cane or beet sugar - made from one glucose and one fructose), lactose (milk sugar - made from one glucose and one galactose), maltose (made of two glucoses linked alpha-1,4) and cellobiose (made of two glucoses linked beta-1,4). The formula of these disaccharides is C12H22O11.
Other examples of disaccharides include trehalose, chitobiose, laminaribiose, kojibiose and xylobiose.
Oligosaccharides and polysaccharides
Main articles: Oligosaccharide and Polysaccharide
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 oligosaccharides responsible for blood group incompatibilities, the alpha-Gal epitope responsible for hyperacute rejection in xenotransplanation, and O-GlcNAc modifications.
Polysaccharides represent an important class of biological polymer. Examples include starch, cellulose, chitin, glycogen, callose, laminarin, xylan, and galactomannan.
