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Disaccharide
A disaccharide (also called a double sugar or biose[1]) is the
sugar formed when two monosaccharides (simple sugars) are
joined by glycosidic linkage. Like monosaccharides,
disaccharides are soluble in water. Three common examples are
sucrose, lactose,[2] and maltose.

Disaccharides are one of the four chemical groupings of

carbohydrates (monosaccharides, disaccharides,
oligosaccharides, and polysaccharides). The most common
types of disaccharides—sucrose, lactose, and maltose—have
twelve carbon atoms, with the general formula C12H22O11. The
differences in these disaccharides are due to atomic Sucrose, a disaccharide formed from
arrangements within the molecule.[3] condensation of a molecule of glucose and a
molecule of fructose
The joining of simple sugars into a double sugar happens by a
condensation reaction, which involves the elimination of a water
molecule from the functional groups only. Breaking apart a double sugar into its two simple sugars is accomplished by
hydrolysis with the help of a type of 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. Each disaccharide is
broken down with the help of a corresponding disaccharidase (sucrase, lactase, and maltase).

Contents
Classification
Formation
Properties
Assimilation
Common disaccharides
References
External links

Classification
There are two functionally different classes of disaccharides:

Reducing disaccharides, in which one monosaccharide, the reducing sugar of the pair, still has a free hemiacetal
unit that can perform as a reducing aldehyde group; cellobiose and maltose are examples of reducing
disaccharides, each with one hemiacetal unit, the other occupied by the glycosidic bond, which prevents it from
acting as a reducing agent.

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Non-reducing disaccharides, in which the component monosaccharides bond through an acetal linkage between
their anomeric centers. This results in neither monosaccharide being left with a hemiacetal unit that is free to act
as a reducing agent. Sucrose and 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.
[4] [5]

Formation
The formation of a disaccharide molecule from two monosaccharide molecules proceeds by displacing a hydroxyl
radical from one molecule and a hydrogen nucleus (a proton) from the other, so that the now vacant bonds on the
monosaccharides join the two monomers together. The vacant bonds on the hydroxyl radical and the proton unite in
their turn, forming a molecule of water, that then goes free. Because of the removal of the water molecule from the
product, the term of convenience for such a process is "dehydration reaction" (also "condensation reaction" or
"dehydration synthesis"). For example, milk sugar (lactose) is a disaccharide made by condensation of one molecule of
each of the monosaccharides glucose and galactose, whereas the disaccharide sucrose in sugar cane and sugar beet, is a
condensation product of glucose and fructose. Maltose, another common disaccharide, is condensed from two glucose
molecules.[6]

The dehydration reaction that bonds monosaccharides into disaccharides (and also bonds monosaccharides into more
complex polysaccharides) forms what are called glycosidic bonds.[7]

Properties
The glycosidic bond can be formed between any hydroxyl group on the component monosaccharide. So, even if both
component sugars are the same (e.g., glucose), different bond combinations (regiochemistry) and stereochemistry
(alpha- or beta-) result in disaccharides that are diastereoisomers with different chemical and physical properties.

Depending on the monosaccharide constituents, disaccharides are sometimes crystalline, sometimes water-soluble,
and sometimes sweet-tasting and sticky-feeling.

Assimilation
Digestion involves breakdown to the monosaccharides.

Common disaccharides

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Disaccharide Unit 1 Unit 2 Bond

Sucrose (table sugar, cane sugar, beet sugar, or saccharose) Glucose Fructose α(1→2)β

Lactulose Galactose Fructose β(1→4)

Lactose (milk sugar) Galactose Glucose β(1→4)

Maltose (malt sugar) Glucose Glucose α(1→4)

Trehalose Glucose Glucose α(1→1)α

Cellobiose Glucose Glucose β(1→4)

Chitobiose Glucosamine Glucosamine β(1→4)

Maltose, cellobiose, and chitobiose are hydrolysis products of the polysaccharides starch, cellulose, and chitin,
respectively.

Less common disaccharides include:[8]

Disaccharide Units Bond

Kojibiose two glucose monomers α(1→2) [9]

Nigerose two glucose monomers α(1→3)

Isomaltose two glucose monomers α(1→6)

β,β-Trehalose two glucose monomers β(1→1)β

α,β-Trehalose two glucose monomers α(1→1)β[10]

Sophorose two glucose monomers β(1→2)

Laminaribiose two glucose monomers β(1→3)

Gentiobiose two glucose monomers β(1→6)

Turanose a glucose monomer and a fructose monomer α(1→3)

Maltulose a glucose monomer and a fructose monomer α(1→4)

Palatinose a glucose monomer and a fructose monomer α(1→6)

Gentiobiulose a glucose monomer and a fructose monomer β(1→6)

Mannobiose two mannose monomers either α(1→2), α(1→3), α(1→4), or α(1→6)

Melibiose a galactose monomer and a glucose monomer α(1→6)

Melibiulose a galactose monomer and a fructose monomer α(1→6)

Rutinose a rhamnose monomer and a glucose monomer α(1→6)

Rutinulose a rhamnose monomer and a fructose monomer β(1→6)

Xylobiose two xylopyranose monomers β(1→4)

References

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1. Biose on www.merriam-webster.org (http://www.merriam-webster.com/medical/biose)

2. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:
(2006–) "disaccharides (http://goldbook.iupac.org/D01776.html)".
3. Biology- A course for O Level. p. 59. ISBN 9810190964.
4. "Nomenclature of Carbohydrates (Recommendations 1996)2-Carb-36 Disaccharides"
(http://www.chem.qmul.ac.uk/iupac/2carb/36.html).
5. "Disaccharides and Oligosaccharides" (http://faculty.virginia.edu/mcgarveylab/Carbsyn/Carblist/html/disacch.html).
Retrieved 2008-01-29.
6. Whitney, Ellie; Sharon Rady Rolfes (2011). Peggy Williams, ed. Understanding Nutrition (Twelfth ed.). California:
Wadsworth, Cengage Learning. p. 100. ISBN 0-538-73465-5.
7. "Glycosidic Link" (http://science.uvu.edu/ochem/index.php/alphabetical/g-h/glycosidic-link/). OChemPal. Utah
Valley University. Retrieved 11 December 2013.
8. F.W.Parrish; W.B.Hahn, G.R.Mandels (July 1968). "Crypticity of Myrothecium verrucaria Spores to Maltose and
Induction of Transport by Maltulose, a Common Maltose Contaminant" (http://jb.asm.org/cgi/reprint/96/1/227.pdf)
(PDF). J. Bacteriol. American Society for Microbiology. 96 (1): 227–233. PMC 252277
(https://www.ncbi.nlm.nih.gov/pmc/articles/PMC252277) . PMID 5690932 (https://www.ncbi.nlm.nih.gov/pubmed
/5690932). Retrieved 2008-11-21.
9. Matsuda, K.; Abe, Y; Fujioka, K (November 1957). "Kojibiose (2-O-alpha-D-Glucopyranosyl-D-Glucose): Isolation
and Structure: Chemical Synthesis". Nature. 180 (4593): 985–6. doi:10.1038/180985a0 (https://doi.org
/10.1038%2F180985a0). PMID 13483573 (https://www.ncbi.nlm.nih.gov/pubmed/13483573).
10. T. Taga; Y. Miwa; Z. Min (1997). "α,β-Trehalose Monohydrate" (http://scripts.iucr.org/cgi-
bin/paper?S0108270196012693). Acta Crystallogr. C. 53 (2): 234–236. doi:10.1107/S0108270196012693
(https://doi.org/10.1107%2FS0108270196012693).

External links
Disaccharides (https://www.nlm.nih.gov/cgi/mesh/2011/MB_cgi?mode=&term=Disaccharides) at the US National
Library of Medicine Medical Subject Headings (MeSH)

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