What Are the Properties of

Carbohydrates?

Last Updated: Jul 21, 2015 | By Ryan Mac

Close up
of individual slicing baguette. Photo CreditJack Hollingsworth/Photodisc/Getty Images

Overview
Carbohydrates, one of the four macromolecules of life, can make up a
large part of your diet on any given day. Carbohydrates are made up of
linked sugar molecules. Carbohydrates range in size from simple
carbohydrates with one or two sugar molecules, to complex
carbohydrates which can have hundreds of molecules linked together,
notes the Harvard School of Public Health.

Energy
The presence of carbohydrates in food gives you a very important source
of energy. The energy comes from the breakdown of the carbohydrates
into its constituent components. Excess carbohydrates not immediately
used for energy gets stored as glycogen. When glycogen storage reaches

capacity, the excess carbohydrates gets stored as fat. While the use of
carbohydrates as an energy source in your body is important in its own
right, the presence of carbohydrates prevents the body from using
protein in the body for energy.

Structure
Carbohydrates begin as molecules of sugar. Each molecule of sugar
consists of a carbon backbone, with hydrogen and oxygen molecules
attached to the carbon at different positions. The varying position of
these atoms is called stereoisomerism and creates different sugars while
maintaining an identical molecular formula. One example, according to
Encyclopaedia Britannica, comes from the sugars fructose and glucose
which each have six carbon atoms, 12 hydrogen atoms and six oxygen
atoms. Carbohydrates have chains of different lengths, but also have
different orientation. Some chains of sugar are straight and even, while
other chains branch off in many directions.

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Simple vs. Complex

Simple and complex carbohydrates define two groups of carbohydrates
commonly associated with foods. Simple carbohydrates are those which
have smaller chains of sugars linked together, and in general provide a
faster source of energy, as they metabolize faster in the body. Complex
carbohydrates have longer chains of sugars and take much more time to

metabolize than simple carbohydrates. Complex carbohydrates include

many foods made of grains, such as pasta and breads.

Chemical features of carbohydrates

1. What are the organic chemical groups
that characterize carbohydrates? How are
carbohydrates classified according to the
presence of those groups?
Carbohydrates are also known as sugars (starches,
cellulose and other substances are carbohydrates
too).
Carbohydrates are polyhydroxylated aldehydes or
polyhydroxylated ketones (polyalcohol aldehydes or
polyalcohol ketones).
Polyhydroxylated aldehydes are called aldoses and
polyhydroxylated ketones are called ketoses.

2. What is the molecular formula of glucose?

How can its structural formula be described?
The molecular formula of glucose is CHO.
Structurally glucose is a hexagonal ring formed by
one atom of oxygen and five atoms of carbon; a
hydroxyl radical and a hydrogen atom bind in each
carbon of the ring, except for one of the carbons
bound to the oxygen of the ring; this carbon binds to a
CHOH radical. Spatial sides of hydroxyl bonds are
alternated.
Carbohydrate Properties Review - Image
Diversity: glucose molecule

Mono, oligo and polysaccharides

3. What are monosaccharides,

oligosaccharides and polysaccharides?
Monosaccharides are simple molecules of
carbohydrates that cannot be broken into smaller
molecules of other carbohydrates. Oligosaccharides
are carbohydrates made by union of a maximum of 10
monosaccharides. Polysaccharides are polymers of
monosaccharides made of more than 10 units of such
monomers. The most important polysaccharides are
cellulose, starch, glycogen and chitin.

4. What is the difference between

monosaccharides and disaccharides? What
are some examples of disaccharides and of
monosaccharides that form them?
Monosaccharides are simple molecules of
carbohydrates that cannot be broken into other
carbohydrates. Glucose and fructose are examples of
monosaccharides. Disaccharides are carbohydrates
made of two monosaccharides and with the loss of

one molecule of water (dehydration). The chemical

bond between two monosaccharides is known as a
glycosidic bond.
Sucrose (table sugar) is a disaccharide made by the
union of one molecule of glucose with one molecule
of fructose. Maltose is a disaccharide made by two
glucose molecules. Lactose (milk sugar) is another
disaccharide and it is created by the union of one
molecule of galactose with one molecule of glucose.

Carbohydrate
From Wikipedia, the free encyclopedia

Lactose is a disaccharide found in milk. It consists of a molecule of Dgalactose and a molecule of D-glucosebonded by beta-1-4 glycosidic linkage.
It has a formula of C12H22O11.
A carbohydrate is a biological molecule consisting of carbon (C), hydrogen (H) and oxygen (O)
atoms, usually with a hydrogen:oxygen atom ratio of 2:1 (as in water); in other words, with
the empirical formula Cm(H2O)n (where m could be different from n).[1] Some exceptions exist; for
example, deoxyribose, a sugar component of DNA,[2] has the empirical formula C5H10O4.
[3]
Carbohydrates are technically hydrates of carbon;[4] structurally it is more accurate to view them
aspolyhydroxy aldehydes and ketones.[5]
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, andpolysaccharides. 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 monosaccharideglucose, 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., 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.[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).

Contents
[hide]

1 Structure

2 Monosaccharides
o

2.1 Classification of monosaccharides

2.2 Ring-straight chain isomerism

2.3 Use in living organisms

3 Disaccharides

4 Nutrition
o

4.1 Classification
5 Metabolism

5.1 Catabolism

6 Carbohydrate chemistry

7 See also

8 References

9 External links

Structure[edit]
Formerly the name "carbohydrate" was used in chemistry for any compound with the formula
Cm (H2O) n. Following this definition, some chemists considered formaldehyde(CH2O) to be the
simplest carbohydrate,[8] while others claimed that title for glycolaldehyde.[9] Today the term is
generally understood in the biochemistry sense, which excludes compounds with only one or two
carbons.
Natural saccharides are generally built of simple carbohydrates called monosaccharides with
general formula (CH2O)n where n is three or more. A typical monosaccharide has the structure H(CHOH)x(C=O)-(CHOH)y-H, that is, an aldehyde or ketone with many hydroxyl groups added, usually
one on each carbon atom that is not part of the aldehyde or ketone functional group. Examples of
monosaccharides are glucose, fructose, and glyceraldehydes. However, some biological substances
commonly called "monosaccharides" do not conform to this formula (e.g., uronic acids and deoxysugars such as fucose) and there are many chemicals that do conform to this formula but are not
considered to be monosaccharides (e.g., formaldehyde CH2O and inositol (CH2O)6).[10]
The open-chain form of a monosaccharide often coexists with a closed ring form where
the aldehyde/ketone carbonyl group carbon (C=O) and hydroxyl group (-OH) react forming
a hemiacetal with a new C-O-C bridge.
Monosaccharides can be linked together into what are called polysaccharides (or oligosaccharides)
in a large variety of 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-acetyl
glucosamine, a nitrogen-containing form of glucose.

Monosaccharides[edit]
Main article: Monosaccharide

D-glucose is an aldohexose with the formula (CH2O)6. The red atoms highlight
thealdehyde group and the blue atoms highlight theasymmetric centerfurthest

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 (CH2O) 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-glyceraldehydes.

Classification of monosaccharides[edit]

The and 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 either have identical absolute configurations (R,R or S,S) (),
or opposite absolute configurations (R,S or S,R) ().[11]
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 arehexoses, and so on.[12] These two
systems of classification are often combined. For example, glucose is analdohexose (a six-carbon
aldehyde), ribose is an aldopentose (a five-carbon aldehyde), and fructose is a ketohexose(a sixcarbon 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 ofisomers may exist for any given monosaccharide formula.
Using Le Bel-van't Hoff rule, the aldohexose D-glucose, for example, has the formula (CH2O) 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.[13]

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.[14]
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.[15] Ribulose and 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 andlactose. 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 Dfructose molecule. The systematic name for sucrose, O--D-glucopyranosyl-(12)-Dfructofuranoside, 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.They
are 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,[16] and
3.57 to 4.12 calories per gram for complex carbohydrate in most other foods. [17] High levels of
carbohydrate are often associated with highly 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. [18] Foods from animal carcass
have the lowest carbohydrate, but milk does contain lactose.
Carbohydrates are a common source of energy in living organisms; however, no carbohydrate is
an essential nutrient in humans.[19]Humans are able to obtain most 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 so far.[19] 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.[20]
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.
[21]
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.[22][23]
[24]
Gluconeogenesis allows humans to synthesize some glucose from specific amino acids: from
the glycerol backbone intriglycerides 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 disaccharides but 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

Biological Compounds
Monosaccharides are carbohydrates with relatively small molecules,
they play quite a key part in life with glucose being the most well
known monosaccharide sugar. The diagram below shows -glucose
(alpha glucose) which differs structurally to -glucose (beta glucose)
with the right-hand side hydrogen being trapped up for -glucose
and down for -glucose.

Triose
Many sugars are produced and used within chemical reactions
within cells. An example of this would be glyceraldehyde, a triose
three-carbon sugar used in early photosynthesis. It has the
molecular formula C3H6O3 and is shown below in a simplified
version.

Pentose
As well as triose sugars there are also pentose sugars and, hence
the name, contain five carbons. An example of a pentose sugar
would be ribose (C5H10O5 and shown in the diagram below) and
deoxyribose (C5H10O4) would be another example.

Hexose
Glucose (C6H12O6) and fructose (C6H12O6) are also sugars but contain
six carbons and so are called hexose sugars.

Disaccharides

Disaccharides consist of two monosaccharide sugars linked

together by a glycosidic bond with the elimination of water in a
condensation reaction.

The diagram above shows two alpha glucose molecules which have
bonded in a condensation reaction, releasing water. The resulting
disaccharide formed is maltose (see table below).
Monosaccharides

Disaccaride

Glucose + Glucose

= Maltose

In Malt

Glucose + Fructose

= Sucrose

In Cane

Glucose + Galactose

= Lactose

In Milk

Polysaccharides

A polysaccharide is a large and complex molecules which are built

from large numbers of monosaccharides linked by glycosidic bonds.
An example of a polysaccaride would be starch (for plants) and
glycogen (for animals). They are both used for storage because they
are very effective at what they do, glucose can be added or taken
away from them very easily.

Starch
Starch is formed from many alpha glucose polymers and because of
the type of bonds form a helix. It also contains many hydrogen
bonds. It works well as an energy store within in plants because its
molecules are compact and insoluble but are easily hydrolysed.
Within starch there are 2 similar molecules. These are Amylose and
Amylopectin.

Amylose
Amylose is a large unbranched chain of -glucose forming 1,4glycosidic bonds (bonds between Carbon 1 in the first molecule and
Carbon 4 in the bonding molecule.) Every 6 risidules it completes 1
coil, which is held by weak hydrogen bonds, because of this
structure it is very compact and takes up little room which is ideal for
storage. On average 30% of all starch samples are Amylose.

Amylopectin
Amylopectin is the remaining 70%. Whereas amylose is straight
chains and doesnt branch; Amylopectin branches every 20
residules as well as coiling every 6. The branches are 1,6-glycosidic
bonds and result in an even more compact molecule.

Starch will not dissolve in water.

It has no osmotic effects.

Is completely inert.

Is easily hydrolised when required for energy.

Glycogen
Glycogen is the main long-term storage molecule for energy in
animals and humans. It too is made of long chains of -glucose
with 1,4-glycosidic bonds but branches every 10 risidules which
makes it even more compact. It is mainly made in the liver but is
stored in muscle tissue where it is readily availible to be used
quickly in respiration.

Lipids (Fats)

The most common type of lipids that youre expected to know

about are triglycerides. Lipids are usually known as fats and
oils.
Lipids like carbohydrates contain carbon, hydrogen and oxygen but
are different because they only contain a small amount of oxygen.
They are formed by condensation reactions between glycerol and
fatty acids, this is a similar reaction to the one shown in the diagram
for disaccharides.

The chemical properties of lipids:

Insoluble in water.

May be solid or liquid at room temperature depending on their

structure and composition.

Proteins

The diagram above shows the structure of a protein, they are

different from carbohydrates and lipids by containing an amino
group which contains nitrogen. Most proteins are very large
molecules formed from long chains of amino acids. Other than the
amino group they have a carboxyl group usually containing a
carbon, two oxygen and a hydrogen (COOH).
As well as the amino and carboxyl group, proteins also have an Rgroup. This R-group is where each protein differs from one another.

Structure of a Protein
Proteins are made up of amino acids in a linear sequence, the
amino group of one amino acid reacts with the carboxyl group of
another amino acid in a condensation reaction releasing water. This
reaction is called a peptide bond and the result of this reaction

would be a dipeptide. If there are more than two amino acids

bonded in this way its called a polypeptide.
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, however, most organisms 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.[25]
Based on the effects on risk of heart disease and obesity,[26] the Institute of Medicine recommends
that American and Canadian adults get between 4565% of dietary energyfrom carbohydrates.
[27]
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).[28]

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 carbohydratewas 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).[29] 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).[30]
In any case, the simple vs. complex chemical distinction has little value for determining the
nutritional quality of carbohydrates.[30] 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.[31]
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.[32]
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.

A triose is a monosaccharide that contains three carbon atoms. An

example is L-Glyceraldehyde.
(There are only three possible trioses: L-Glyceraldehyde, DGlyceraldehyde, Dihydroxyacetone)
A tetrose is a monosaccharide with 4 carbon atoms. An example is DErythrose.
Glucose and fructose are examples of hexoses
Arabinose and ribose are examples of pentoses.