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A disaccharide (also called a double sugar or ''biose'') is the
sugar Sugar is the generic name for sweet-tasting, soluble carbohydrate is a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosacc ...

sugar
formed when two
monosaccharide Monosaccharides (from Greek#REDIRECT Greek Greek may refer to: Greece Anything of, from, or related to Greece Greece ( el, Ελλάδα, , ), officially the Hellenic Republic, is a country located in Southeast Europe. Its population is ap ...
s are joined by
glycosidic A glycosidic bond or glycosidic linkage is a type of covalent bond A covalent bond is a chemical bond A chemical bond is a lasting attraction between atoms, ions or molecules that enables the formation of chemical compounds. The bond may ...
linkage. Like monosaccharides, disaccharides are simple sugars
soluble Solubility is the property of a solid, liquid or gaseous chemical substance called ''solution, solute'' to dissolve in a solid, liquid or gaseous solvent. The solubility of a substance fundamentally depends on the Physical property, physical an ...

soluble
in water. Three common examples are
sucrose Sucrose is a type of sugar Sugar is the generic name for , soluble s, many of which are used in food. Simple sugars, also called s, include , , and . Compound sugars, also called s or double sugars, are molecules made of two monosacchari ...

sucrose
,
lactose Lactose, a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar Sugar is the generic name for sweet-tasting, soluble carbohydrate is a disaccharide found in animal milk. It consists of a molecule of D-g ...

lactose
, and
maltose} Maltose ( or ), also known as maltobiose or malt sugar, is a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disacchari ...

maltose
. Disaccharides are one of the four chemical groupings of
carbohydrate is a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common ex ...
s (
monosaccharide Monosaccharides (from Greek#REDIRECT Greek Greek may refer to: Greece Anything of, from, or related to Greece Greece ( el, Ελλάδα, , ), officially the Hellenic Republic, is a country located in Southeast Europe. Its population is ap ...
s, disaccharides,
oligosaccharide An oligosaccharide (/ˌɑlɪgoʊˈsækəˌɹaɪd/; from the Greek ὀλίγος ''olígos'', "a few", and σάκχαρ ''sácchar'', "sugar") is a saccharide is a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sug ...
s, and
polysaccharide Polysaccharides (), or polycarbohydrates, are the most abundant found in . They are long chain carbohydrates composed of units bound together by . This carbohydrate can react with water () using as catalyst, which produces constituent sugars ...
s). The most common types of disaccharides—
sucrose Sucrose is a type of sugar Sugar is the generic name for , soluble s, many of which are used in food. Simple sugars, also called s, include , , and . Compound sugars, also called s or double sugars, are molecules made of two monosacchari ...

sucrose
,
lactose Lactose, a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar Sugar is the generic name for sweet-tasting, soluble carbohydrate is a disaccharide found in animal milk. It consists of a molecule of D-g ...

lactose
, and
maltose} Maltose ( or ), also known as maltobiose or malt sugar, is a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disacchari ...

maltose
—have 12
carbon Carbon (from la, carbo "coal") is a with the C and 6. It is lic and —making four s available to form s. It belongs to group 14 of the periodic table. Carbon makes up only about 0.025 percent of Earth's crust. Three occur naturally, ...

carbon
atoms, with the general formula C12H22O11. The differences in these disaccharides are due to atomic arrangements within the molecule. The joining of monosaccharides into a double sugar happens by a
condensation reaction In , a condensation reaction is a type of in which two s are to form a single molecule, usually with the loss of a small molecule such as . If water is lost, the reaction is also known as a . However other molecules can also be lost, such as , , ...
, which involves the elimination of a water molecule from the
functional group In organic chemistry, a functional group is a substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions re ...
s only. Breaking apart a double sugar into its two monosaccharides is accomplished by
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution Substitution may refer to: Arts and media *Chord substitution, in music, swapping one chord for ...

hydrolysis
with the help of a type of
enzyme Enzymes () are protein Proteins are large s and s that comprise one or more long chains of . Proteins perform a vast array of functions within organisms, including , , , providing and , and from one location to another. Proteins diff ...

enzyme
called a disaccharidase. As building the larger sugar ejects a water molecule, breaking it down consumes a water molecule. These reactions are vital in
metabolism Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life Life is a characteristic that distinguishes physical entities that have biological processes, such as Cell signaling, signaling and self-sustaining ...

metabolism
. Each disaccharide is broken down with the help of a corresponding disaccharidase (
sucraseSucrase is a digestive enzyme that catalysis, catalyzes the hydrolysis of sucrose to its subunits fructose and glucose. One form, sucrase-isomaltase, is secreted in the small intestine on the brush border. The sucrase enzyme invertase, which occurs m ...

sucrase
,
lactase Lactase is an enzyme Enzymes () are proteins that act as biological catalysts (biocatalysts). Catalysts accelerate chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme conve ...

lactase
, and
maltase Maltase (, ''alpha-glucosidase'', ''glucoinvertase'', ''glucosidosucrase'', ''maltase-glucoamylase'', ''alpha-glucopyranosidase'', ''glucosidoinvertase'', ''alpha-D-glucosidase'', ''alpha-glucoside hydrolase'', ''alpha-1,4-glucosidase'', ''alpha ...
).


Classification

There are two functionally different classes of disaccharides: *
Reducing disaccharides
Reducing disaccharides
, in which one monosaccharide, the
reducing sugar A reducing sugar is any sugar that is capable of acting as a reducing agent because it has a free aldehyde group or a free ketone group. All monosaccharides are reducing sugars, along with some disaccharides, some oligosaccharides, and some polysac ...

reducing sugar
of the pair, still has a free
hemiacetal A hemiacetal or a hemiketal have the general formula R1R2C(OH)OR, where R1 or R2 is hydrogen or an organic substituent. They generally result from the addition of an alcohol File:Alcohol general.svg, upright=0.8, The bond angle between a hydrox ...

hemiacetal
unit that can perform as a reducing
aldehyde Chemically, an aldehyde is a compound containing a functional group In organic chemistry, a functional group is a substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same fu ...

aldehyde
group;
lactose Lactose, a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar Sugar is the generic name for sweet-tasting, soluble carbohydrate is a disaccharide found in animal milk. It consists of a molecule of D-g ...

lactose
,
maltose} Maltose ( or ), also known as maltobiose or malt sugar, is a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disacchari ...

maltose
and
cellobiose Cellobiose is a disaccharide with the formula (C6H7(OH)4O)2O. It is classified as a reducing sugar. In terms of its chemical structure, it is derived from the condensation of a pair β-glucose molecules forging a β(1→4) bond. It can be hydro ...

cellobiose
are examples of reducing disaccharides, each with one hemiacetal unit, the other occupied by the
glycosidic A glycosidic bond or glycosidic linkage is a type of covalent bond A covalent bond is a chemical bond A chemical bond is a lasting attraction between atoms, ions or molecules that enables the formation of chemical compounds. The bond may ...

glycosidic
bond, which prevents it from acting as a
reducing agent A reducing agent (also called a reductant, reducer, or electron donor) is an element or compound that loses or "donates" an electron The electron is a subatomic particle In physical sciences, subatomic particles are smaller than atom ...
. They can easily be detected by the Woehlk test or Fearon's test on methylamine. *
Non-reducing disaccharides
Non-reducing disaccharides
, in which the component monosaccharides bond through an
acetal An acetal is a functional group In organic chemistry, a functional group is a substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the sam ...

acetal
linkage between their
anomer An anomer is a type of geometric variation found at certain atoms in carbohydrate is a disaccharide found in animal milk. It consists of a molecule of D-galactose and a molecule of D-glucose bonded by beta-1-4 glycosidic linkage. A carboh ...
ic centers. This results in neither monosaccharide being left with a hemiacetal unit that is free to act as a
reducing agent A reducing agent (also called a reductant, reducer, or electron donor) is an element or compound that loses or "donates" an electron The electron is a subatomic particle In physical sciences, subatomic particles are smaller than atom ...
.
Sucrose Sucrose is a type of sugar Sugar is the generic name for , soluble s, many of which are used in food. Simple sugars, also called s, include , , and . Compound sugars, also called s or double sugars, are molecules made of two monosacchari ...

Sucrose
and
trehalose Trehalose (from Turkish 'trehala' – a sugar derived from insect cocoons + -ose) is a sugar Sugar is the generic name for Sweetness, sweet-tasting, soluble carbohydrates, many of which are used in food. Table sugar, granulated sugar, or regu ...

trehalose
are examples of non-reducing disaccharides because their glycosidic bond is between their respective hemiacetal carbon atoms. The reduced chemical reactivity of the non-reducing sugars in comparison to reducing sugars, may be an advantage where stability in storage is important.


Formation

The formation of a disaccharide molecule from two
monosaccharide Monosaccharides (from Greek#REDIRECT Greek Greek may refer to: Greece Anything of, from, or related to Greece Greece ( el, Ελλάδα, , ), officially the Hellenic Republic, is a country located in Southeast Europe. Its population is ap ...
molecules proceeds by displacing a
hydroxy
hydroxy
group from one molecule and a
hydrogen nucleus
hydrogen nucleus
(a
proton A proton is a subatomic particle, symbol or , with a positive electric charge of +1''e'' elementary charge and a mass slightly less than that of a neutron. Protons and neutrons, each with masses of approximately one atomic mass unit, are collecti ...

proton
) from the other, so that the now vacant bonds on the monosaccharides join the two
monomer In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during a ...

monomer
s together. Because of the removal of the water molecule from the product, the term of convenience for such a process is "
dehydration reaction In chemistry, a dehydration reaction, also known as Zimmer's hydrogenesis, is a chemical reaction that involves the loss of water from the reacting molecule or ion. It is the most common type of condensation reaction. Dehydration reactions are co ...
" (also "
condensation reaction In , a condensation reaction is a type of in which two s are to form a single molecule, usually with the loss of a small molecule such as . If water is lost, the reaction is also known as a . However other molecules can also be lost, such as , , ...
" or "
dehydration synthesis In chemistry, a dehydration reaction (a.k.a. Condensation polymer, condensation reaction) is a conversion that involves the loss of water from the reacting molecule or ion. Dehydration reactions are common processes, the reverse of a hydration reac ...
"). For example, milk sugar (
lactose Lactose, a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar Sugar is the generic name for sweet-tasting, soluble carbohydrate is a disaccharide found in animal milk. It consists of a molecule of D-g ...

lactose
) is a disaccharide made by condensation of one molecule of each of the monosaccharides
glucose Glucose is a simple with the . Glucose is the most abundant , a subcategory of s. Glucose is mainly made by and most during from water and carbon dioxide, using energy from sunlight, where it is used to make in s, the most abundant carbohydr ...

glucose
and
galactose Galactose (, '' galacto-'' + ''-ose The suffix In linguistics Linguistics is the science, scientific study of language. It encompasses the analysis of every aspect of language, as well as the methods for studying and modeling them. ...
, whereas the disaccharide
sucrose Sucrose is a type of sugar Sugar is the generic name for , soluble s, many of which are used in food. Simple sugars, also called s, include , , and . Compound sugars, also called s or double sugars, are molecules made of two monosacchari ...

sucrose
in sugar cane and sugar beet, is a condensation product of
glucose Glucose is a simple with the . Glucose is the most abundant , a subcategory of s. Glucose is mainly made by and most during from water and carbon dioxide, using energy from sunlight, where it is used to make in s, the most abundant carbohydr ...

glucose
and
fructose Fructose, or fruit sugar, is a ketonic simple sugar Monosaccharides (from Greek language, Greek ''wikt:μόνος, monos'': single, ''sacchar'': sugar), also called simple sugars, are the simplest form of sugar and the most basic units (monomers ...

fructose
.
Maltose} Maltose ( or ), also known as maltobiose or malt sugar, is a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disacchari ...

Maltose
, another common disaccharide, is condensed from two glucose molecules. The dehydration reaction that bonds monosaccharides into disaccharides (and also bonds monosaccharides into more complex
polysaccharide Polysaccharides (), or polycarbohydrates, are the most abundant found in . They are long chain carbohydrates composed of units bound together by . This carbohydrate can react with water () using as catalyst, which produces constituent sugars ...
s) forms what are called
glycosidic bond A glycosidic bond or glycosidic linkage is a type of covalent bond A covalent bond is a chemical bond A chemical bond is a lasting attraction between atoms, ions or molecules that enables the formation of chemical compounds. The bond may ...
s.


Properties

The glycosidic bond can be formed between any hydroxy group on the component monosaccharide. So, even if both component
sugar Sugar is the generic name for sweet-tasting, soluble carbohydrate is a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosacc ...

sugar
s are the same (e.g.,
glucose Glucose is a simple with the . Glucose is the most abundant , a subcategory of s. Glucose is mainly made by and most during from water and carbon dioxide, using energy from sunlight, where it is used to make in s, the most abundant carbohydr ...

glucose
), different bond combinations (regiochemistry) and
stereochemistry s. Stereochemistry focuses on stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dim ...

stereochemistry
(''alpha-'' or ''beta-'') result in disaccharides that are
diastereoisomer Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomers are defined as non-mirror image non-identical stereoisomers. Hence, they occur when two or more stereoisomers of a compound have different configurations ...
s with different chemical and physical properties. Depending on the
monosaccharide Monosaccharides (from Greek#REDIRECT Greek Greek may refer to: Greece Anything of, from, or related to Greece Greece ( el, Ελλάδα, , ), officially the Hellenic Republic, is a country located in Southeast Europe. Its population is ap ...
constituents, disaccharides are sometimes crystalline, sometimes water-soluble, and sometimes sweet-tasting and sticky-feeling. Disaccharides can serve as
functional group In organic chemistry, a functional group is a substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions re ...
s by forming glycosidic bonds with other organic compounds, forming
bioside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. T ...
s.


Assimilation

Digestion involves breakdown to the monosaccharides.


Common disaccharides

: Maltose, cellobiose, and chitobiose are
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution Substitution may refer to: Arts and media *Chord substitution, in music, swapping one chord for ...

hydrolysis
products of the
polysaccharide Polysaccharides (), or polycarbohydrates, are the most abundant found in . They are long chain carbohydrates composed of units bound together by . This carbohydrate can react with water () using as catalyst, which produces constituent sugars ...
s
starch Starch or amylum is a consisting of numerous units joined by s. This is produced by most green s for energy storage. Worldwide, it is the most common carbohydrate in human diets, and is contained in large amounts in s like , es, (corn), , ...
,
cellulose Cellulose is an organic compound with the chemical formula, formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of glycosidic bond, β(1→4) linked glucose, D-glucose units. Cellulose is an important stru ...

cellulose
, and
chitin units that repeat to form long chains in β-(1→4)-linkage. of the chitin molecule. Chitin ( carbon, C8H13O5N)n ( ) is a long-chain polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical su ...

chitin
, respectively. Less common disaccharides include: :


References


External links

* {{Authority control Carbohydrate chemistry