Disaccharide

Sucrose, a disaccharide formed from condensation of a molecule of glucose and a molecule of fructose

A disaccharide (also called a double sugar or biose)[1] is the sugar formed when two monosaccharides are joined by glycosidic linkage.[2] Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, lactose, 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 12 carbon atoms, with the general formula C12H22O11. The differences in these disaccharides are due to atomic arrangements within the molecule.[3]

The joining of monosaccharides 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 monosaccharides 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).

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; lactose, maltose and cellobiose 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. They can easily be detected by the Woehlk test or Fearon's test on methylamine.[4]
  • 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.[5][6]

Formation

The formation of a disaccharide molecule from two monosaccharide molecules proceeds by displacing a hydroxy group from one molecule and a hydrogen nucleus (a proton) from the other, so that the new vacant bonds on the monosaccharides join the two monomers together. 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.[7]

The dehydration reaction that bonds monosaccharides into disaccharides (and also bonds monosaccharides into more complex polysaccharides) forms what are called glycosidic bonds.[8]

Properties

The glycosidic bond can be formed between any hydroxy 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. Disaccharides can serve as functional groups by forming glycosidic bonds with other organic compounds, forming glycosides.

Assimilation

See also: Carbohydrate digestion

Digestion of disaccharides involves breakdown into monosaccharides.

Common disaccharides

Disaccharide Unit 1 Unit 2 Bond
Sucrose (table sugar, cane sugar, beet sugar, or saccharose) Glucose Fructose α(1→2)β
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:[9]

Disaccharide Units Bond
Kojibiose Two glucoses α(1→2)[10]
Nigerose Two glucoses α(1→3)
Isomaltose Two glucoses α(1→6)
β,β-Trehalose Two glucoses β(1→1)β
α,β-Trehalose Two glucoses α(1→1)β[11]
Sophorose Two glucoses β(1→2)
Laminaribiose Two glucoses β(1→3)
Gentiobiose Two glucoses β(1→6)
Trehalulose One glucose and one fructose α(1→1)
Turanose One glucose and one fructose α(1→3)
Maltulose One glucose and one fructose α(1→4)
Leucrose One glucose and one fructose α(1→5)
Isomaltulose One glucose and one fructose α(1→6)
Gentiobiulose One glucose and one fructose β(1→6)
Mannobiose Two mannoses Either α(1→2), α(1→3), α(1→4), or α(1→6)
Melibiose One galactose and one glucose α(1→6)
Allolactose One galactose and one glucose β(1→6)
Melibiulose One galactose and one fructose α(1→6)
Lactulose One galactose and one fructose β(1→4)
Rutinose One rhamnose and one glucose α(1→6)
Rutinulose One rhamnose and one fructose β(1→6)
Xylobiose Two xylopyranoses β(1→4)

References

  1. ^ "Biose". Merriam-Webster.
  2. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "disaccharides". doi:10.1351/goldbook.D01776
  3. ^ Kwan, Lam Peng (2000). Biology- A course for O Level. p. 59. ISBN 9810190964.
  4. ^ Ruppersberg, Klaus; Herzog, Stefanie; Kussler, Manfred W.; Parchmann, Ilka (2019). "How to visualize the different lactose content of dairy products by Fearon's test and Woehlk test in classroom experiments and a new approach to the mechanisms and formulae of the mysterious red dyes". Chemistry Teacher International. 2 (2). doi:10.1515/cti-2019-0008.
  5. ^ "Nomenclature of Carbohydrates (Recommendations 1996): 2-Carb-36". chem.qmul.ac.uk. Archived from the original on 2017-08-26. Retrieved 2010-07-21.
  6. ^ "Disaccharides and Oligosaccharides". University of Virginia Faculty and Lab Site. Archived from the original on 2018-11-18. Retrieved 2008-01-29.
  7. ^ Whitney, Ellie; Sharon Rady Rolfes (2011). Peggy Williams (ed.). Understanding Nutrition (Twelfth ed.). California: Wadsworth, Cengage Learning. p. 100. ISBN 978-0-538-73465-3.
  8. ^ "Glycosidic Link". OChemPal. Utah Valley University. Archived from the original on May 12, 2013. Retrieved 11 December 2013.
  9. ^ Parrish, F.W.; Hahn, W.B.; Mandels, G.R. (July 1968). "Crypticity of Myrothecium verrucaria Spores to Maltose and Induction of Transport by Maltulose, a Common Maltose Contaminant". J. Bacteriol. 96 (1). American Society for Microbiology: 227–233. doi:10.1128/JB.96.1.227-233.1968. PMC 252277. PMID 5690932.
  10. ^ 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. Bibcode:1957Natur.180..985M. doi:10.1038/180985a0. PMID 13483573.
  11. ^ T. Taga; Y. Miwa; Z. Min (1997). "α,β-Trehalose Monohydrate". Acta Crystallogr. C. 53 (2): 234–236. doi:10.1107/S0108270196012693.

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