Disaccharide Information & Disaccharide Links at HealthHaven.com

Sucrose, a common disaccharide

A disaccharide is the carbohydrate formed when two monosaccharides undergo a condensation reaction which involves the elimination of a small molecule, such as water, from the functional groups only. Like monosaccharides, disaccharides also dissolve in water, taste sweet and are called sugars.^[1]

'Disaccharide' is one of the four chemical groupings of carbohydrates (monosaccharide, disaccharide, oligosaccharide, and polysaccharide).

[edit] Classification

There are two basic types of disaccharides: reducing disaccharides, in which the monosaccharide components are bonded by hydroxyl groups; and non-reducing disaccharides, in which the components bond through their anometric centers.^[2]

[edit] Formation

It is formed when two monosaccharides are joined together and a molecule of water is removed. For example; milk sugar (lactose) is made from glucose and galactose whereas cane sugar (sucrose) is made from glucose and fructose.

The two monosaccharides are bonded via a dehydration reaction (also called a condensation reaction or dehydration synthesis) that leads to the loss of a molecule of water and formation of a glycosidic bond.

[edit] 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.

[edit] Common disaccharides

Disaccharide	Unit 1	Unit 2	Bond
Sucrose (table sugar, cane sugar, saccharose, or beet sugar)	glucose	fructose	α(1→2)
Lactulose	galactose	fructose	β(1→4)
Lactose (milk sugar)	galactose	glucose	β(1→4)
Maltose	glucose	glucose	α(1→4)
Trehalose	glucose	glucose	α(1→1)α
Cellobiose	glucose	glucose	β(1→4)

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

Less common disaccharides include^[3]:

Disaccharide	Units	Bond
Kojibiose	two glucose monomers	α(1→2) ^[4]
Nigerose	two glucose monomers	α(1→3)
Isomaltose	two glucose monomers	α(1→6)
β,β-Trehalose	two glucose monomers	β(1→1)
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)

[edit] References

^ International Union of Pure and Applied Chemistry. "disaccharides". Compendium of Chemical Terminology Internet edition.
^ "Disaccharides and Oligiosaccharides". http://faculty.virginia.edu/mcgarveylab/Carbsyn/Carblist/html/disacch.html. Retrieved 2008-01-29.
^ F.W.Parrish; W.B.Hahn,G.R.Mandels} (July 1968). "[http://jb.asm.org/cgi/reprint/96/1/227.pdf Crypticity of Myrothecium verrucaria Spores to Maltose and Induction of Transport by Maltulose, a Common Maltose Contaminant]". J. Bacteriol. (American Society for Microbiology) 96 (1): 227-233. http://jb.asm.org/cgi/reprint/96/1/227.pdf. Retrieved 2008-11-21.
^ Matsuda, K. (November 1957). "Kojibiose (2-O-alpha-D-Glucopyranosyl-D-Glucose): Isolation and Structure: Chemical Synthesis". Nature 180: 985. doi:10.1038/180985a0.

[edit] External links

MeSH Disaccharides

[0] International Union of Pure and Applied Chemistry. "disaccharides". Compendium of Chemical Terminology Internet edition.

[1] "Disaccharides and Oligiosaccharides". http://faculty.virginia.edu/mcgarveylab/Carbsyn/Carblist/html/disacch.html. Retrieved 2008-01-29.

[2] F.W.Parrish; W.B.Hahn,G.R.Mandels} (July 1968). "[http://jb.asm.org/cgi/reprint/96/1/227.pdf Crypticity of Myrothecium verrucaria Spores to Maltose and Induction of Transport by Maltulose, a Common Maltose Contaminant]". J. Bacteriol. (American Society for Microbiology) 96 (1): 227-233. http://jb.asm.org/cgi/reprint/96/1/227.pdf. Retrieved 2008-11-21.

[3] Matsuda, K. (November 1957). "Kojibiose (2-O-alpha-D-Glucopyranosyl-D-Glucose): Isolation and Structure: Chemical Synthesis". Nature 180: 985. doi:10.1038/180985a0.

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