A carbohydrate is a biological molecule consisting of carbon (C), hydrogen (H)

and oxygen (O) atoms, usually with a hydrogenoxygen atom ratio of 2:1 (as in
water)
The term is most common in biochemistry, where it is a synonym of saccharide, a
group that includes sugars, starch, and cellulose.
The saccharides are divided into four chemical groups: monosaccharides,
disaccharides, oligosaccharides, and polysaccharides.
In general, the monosaccharides and disaccharides, which are smaller
(lower molecular weight) carbohydrates, are commonly referred to as sugars. [6]
The word saccharide comes from the Greek word (skkharon), 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, grape sugar is the monosaccharide glucose, cane sugar is the
disaccharide sucrose, and milk sugar is the disaccharide lactose (see illustration).

Carbohydrates perform numerous roles in living organisms.

Polysaccharides serve for the storage of energy (e.g. starchand 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.[7]
In food science and in many informal contexts, the term carbohydrate often means
any food that is particularly rich in the complex carbohydrate starch (such as
cereals, bread and pasta) or simple carbohydrates, such as sugar (found in
candy, jams, and desserts).

Often in lists of nutritional information, such as the USDA National Nutrient

Database, the term "carbohydrate" (or "carbohydrate by difference") is used for
everything other than water, protein, fat, ash, and ethanol. [8] This will include
chemical compounds such as acetic or lactic acid, which are not normally
considered carbohydrates. It also includes "dietary fiber" which is a carbohydrate
but which does not contribute much in the way of food energy (calories), even
though it is often included in the calculation of total food energy just as though it
were a sugar.[9]

Division[edit]
They may be classified according to their degree of polymerization and may be
divided initially into three principal groups, namely sugars, oligosaccharides and
polysaccharides[13]
The major dietary carbohydrates
Class (DP*) Subgroup Components
Sugars (12) Monosaccharides Glucose, galactose, fructose, xylose
Disaccharides Sucrose, lactose, maltose, trehalose
 Polyols Sorbitol, mannitol
Malto-
Maltodextrins
Oligosaccharide oligosaccharides
s (39) Other Raffinose, stachyose, fructo-
oligosaccharides oligosaccharides
Amylose, amylopectin, modified
Starch
Polysaccharides starches
(>9) Non-starch Cellulose, hemicellulose, pectins, hydr
polysaccharides ocolloids
DP * = Degree of polymerization
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. 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-glyceraldehydes.
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.[15] 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 stereo centers with two possible
configurations each (R or S). Because of this asymmetry, a number of isomers may
exist for any given monosaccharide formula. Using Le Bel-van't Hoff rule, the
aldohexose D-glucose, for example, has the formula (CH 2O)6, of which four of its six
carbons atoms are stereogenic, making D-glucose one of 2 4=16
possible stereoisomers. In the case of glyceraldehydes, an aldotriose, there is one
pair of possible stereoisomers, which are enantiomers and epimers. 1, 3-
dihydroxyacetone, the ketose corresponding to the aldose glyceraldehydes, is a
symmetric molecule with no stereo centers. 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.[16]
Ring-straight chain isomerism[edit]
Glucose can exist in both a straight-chain and ring form.
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.[17]
During the conversion from straight-chain form to the 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 is
called anomers. In the 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 anomer.
Use in living organisms[edit]
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. The most abundant
carbohydrate, cellulose, is a structural component of the cell wall of plants and
many forms of algae. Ribose is a component of RNA. Deoxyribose is a component
of DNA. Lyxose is a component of lyxoflavin found in the human heart.
[18]
Ribuloseand xylulose occur in the pentose phosphate pathway. Galactose, a
component of milk sugar lactose, is found in galactolipids in plant cell
membranes and in glycoproteins in many tissues. Mannose occurs in human
metabolism, especially in the glycosylation of certain proteins. Fructose, or fruit
sugar, is found in many plants and in humans, it is metabolized in the liver,
absorbed directly into the intestines during digestion, and found
in semen. Trehalose, a major sugar of insects, is rapidly hydrolyzed into two glucose
molecules to support continuous flight.
Disaccharides[edit]
Sucrose, also known as table sugar, is a common disaccharide. It is composed of two
monosaccharides: D-glucose (left) and D-fructose (right).
Main article: Disaccharide
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 groupfrom 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-fructosemolecule. The systematic name for sucrose, O-
-D-glucopyranosyl-(12)-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 -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--D-galactopyranosyl-(14)-D-glucopyranose. Other notable
disaccharides include maltose (two D-glucoses linked -1,4) and cellulobiose (two D-
glucoses linked -1,4). Disaccharides can be classified into two types: reducing and
non-reducing disaccharides. If the functional group is present in bonding with
another sugar unit, it is called a reducing disaccharide or biose.
Nutrition[edit]
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Grain products: rich sources of carbohydrates
Carbohydrate consumed in food yields 3.87 calories of energy per gram for simple
sugars,[19] and 3.57 to 4.12 calories per gram for complex carbohydrate in most
other foods.[20] Relatively high levels of carbohydrate are associated with processed
foods or refined foods made from plants, including sweets, cookies and candy, table
sugar, honey, soft drinks, breads and crackers, jams and fruit products, pastas and
breakfast cereals. Lower amounts of carbohydrate are usually associated with
unrefined foods, including beans, tubers, rice, and unrefined fruit. [21] Animal-based
foods generally have the lowest carbohydrate levels, although milk does contain a
high proportion of lactose.
Carbohydrates are a common source of energy in living organisms; however, no
carbohydrate is an essential nutrient in humans.[22] Humans are able to obtain all of
their energy requirement from protein and fats, though the potential for some
negative health effects of extreme carbohydrate restriction remains, as the issue
has not been studied extensively yet.[22] However, in the case of dietary fiber
indigestible carbohydrates which are not a source of energy inadequate intake can
lead to significant increases in mortality. [23]
Following a diet consisting of very low amounts of daily carbohydrate for several
days will usually result in higher levels of blood ketone bodies than an isocaloric diet
with similar protein content.[24] This relatively high level of ketone bodies is
commonly known as ketosis and is very often confused with the potentially fatal
condition often seen in type 1 diabetics known as diabetic ketoacidosis. Somebody
suffering ketoacidosis will have much higher levels of blood ketone bodies along
with high blood sugar, dehydration and electrolyte imbalance.
Long-chain fatty acids cannot cross the bloodbrain barrier, but the liver can break
these down to produce ketones. However, the medium-chain fatty acids octanoic
and heptanoic acids can cross the barrier and be used by the brain, which normally
relies upon glucose for its energy. [25][26][27] Gluconeogenesis allows humans to
synthesize some glucose from specific amino acids: from the glycerol backbone
in triglycerides and in some cases from fatty acids.
Organisms typically cannot metabolize all types of carbohydrate to yield energy.
Glucose is a nearly universal and accessible source of energy. Many organisms also
have the ability to metabolize other monosaccharides and disaccharidesbut glucose
is often metabolized first. In Escherichia coli, for example, the lac operon will
express enzymes for the digestion of lactose when it is present, but if both lactose
and glucose are present the lac operon is repressed, resulting in the glucose being
used first (see: Diauxie). Polysaccharides are also common sources of energy. Many
organisms can easily break down starches into glucose; most organisms, however,
cannot metabolize cellulose or other polysaccharides like chitin and arabinoxylans.
These carbohydrate types can be metabolized by some bacteria and
protists. Ruminants and termites, for example, use microorganisms to process
cellulose. Even though these complex carbohydrates are not very digestible, they
represent an important dietary element for humans, called dietary fiber. Fiber
enhances digestion, among other benefits. [28]
Based on the effects on risk of heart disease and obesity, [29] the Institute of
Medicine recommends that American and Canadian adults get between 4565%
of dietary energy from carbohydrates.[30] The Food and Agriculture
Organization and World Health Organization jointly recommend that national dietary
guidelines set a goal of 5575% of total energy from carbohydrates, but only 10%
directly from sugars (their term for simple carbohydrates). [31]
Classification[edit]
Nutritionists often refer to carbohydrates as either simple or complex. However, the
exact distinction between these groups can be ambiguous. 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 was
intended to distinguish sugars from other carbohydrates (which were perceived to
be nutritionally superior).[32] However, the report put "fruit, vegetables and whole-
grains" in the complex carbohydrate column, despite the fact that these may
contain sugars as well as polysaccharides. This confusion persists as today some
nutritionists use the term complex carbohydrate to refer to any sort of digestible
saccharide present in a whole food, where fiber, vitamins and minerals are also
found (as opposed to processed carbohydrates, which provide energy but few other
nutrients). The standard usage, however, is to classify carbohydrates chemically:
simple if they are sugars (monosaccharides and disaccharides) and complex if they
are polysaccharides (or oligosaccharides).[33]
In any case, the simple vs. complex chemical distinction has little value for
determining the nutritional quality of carbohydrates. [33] Some simple carbohydrates
(e.g. fructose) raise blood glucose slowly, while some complex carbohydrates
(starches), especially if processed, raise blood sugar rapidly. The speed of digestion
is determined by a variety of factors including which other nutrients are consumed
with the carbohydrate, how the food is prepared, individual differences in
metabolism, and the chemistry of the carbohydrate. [34]
The USDA's Dietary Guidelines for Americans 2010 call for moderate- to high-
carbohydrate consumption from a balanced diet that includes six one-ounce
servings of grain foods each day, at least half from whole grain sources and the rest
from enriched.[35]
The glycemic index (GI) and glycemic load concepts have been developed to
characterize food behavior during human digestion. They rank carbohydrate-rich
foods based on the rapidity and magnitude of their effect on blood glucose levels.
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. 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.
Metabolism[edit]
Main article: Carbohydrate metabolism
Carbohydrate metabolism denotes the various biochemical processes
responsible for the formation, breakdown and interconversion of carbohydrates
in living organisms.
The most important carbohydrate is glucose, a simple sugar (monosaccharide) that
is metabolized by nearly all known organisms. Glucose and other carbohydrates are
part of a wide variety of metabolic pathways across species: plantssynthesize
carbohydrates from carbon dioxide and water by photosynthesis storing the
absorbed energy internally, often in the form of starch or lipids. Plant components
are consumed by animals and fungi, and used as fuel for cellular respiration.
Oxidation of one gram of carbohydrate yields approximately 4 kcal of energy, while
the oxidation of one gram of lipids yields about 9 kcal. Energy obtained from
metabolism (e.g., oxidation of glucose) is usually stored temporarily within cells in
the form of ATP.[36] Organisms capable of aerobic respiration metabolize glucose
and oxygen to release energy with carbon dioxide and water as byproducts.
Catabolism[edit]
Catabolism is the metabolic reaction which cells undergo to extract energy. There
are two major metabolic pathways of monosaccharide catabolism: glycolysis and
the citric acid cycle.
In glycolysis, 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.
Carbohydrate chemistry[edit]
Carbohydrate chemistry is a large and economically important branch of organic
chemistry. Some of the main organic reactions that involve carbohydrates are:
Carbohydrate acetalisation
Cyanohydrin reaction
Lobry-de Bruyn-van Ekenstein transformation
Amadori rearrangement
Nef reaction
Wohl degradation
KoenigsKnorr reaction
Carbohydrate digestion