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Disaccharide

From Wikipedia, the free encyclopedia
Complex sugar
Sucrose, a disaccharide formed from condensation of a molecule of glucose and a molecule of fructose

Adisaccharide (also called adouble sugar)[1] is asugar formed when twomonosaccharides are joined byglycosidic linkage.[2] Like monosaccharides, disaccharides are white solids that aresoluble in water. Common examples aresucrose,lactose, andmaltose.[3]

Related to disaccharides are othercarbohydrates: monosaccharides, their precursors, and the largeroligosaccharides andpolysaccharides). CThe joining of monosaccharides into a double sugar happens by acondensation reaction, shown here in the case of two hexoses:

2 C6H12O6 → C12H22O11 + H2O

Breaking apart a double sugar into its two monosaccharides is accomplished byhydrolysis with the help of a type ofenzyme called adisaccharidase. As building the larger sugar ejects a water molecule, breaking it down consumes a water molecule. These reactions are vital inmetabolism. Each disaccharide is broken down with the help of a corresponding disaccharidase (sucrase,lactase, andmaltase).

Classification

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There are two functionally different classes of disaccharides:

  • Reducing disaccharides, in which one monosaccharide, thereducing sugar of the pair, still has a freehemiacetal unit that can perform as a reducingaldehyde group;lactose,maltose andcellobiose are examples of reducing disaccharides, each with one hemiacetal unit, the other occupied by theglycosidic bond, which prevents it from acting as areducing agent. They can easily be detected by the Woehlk test or Fearon's test onmethylamine.[4]
  • Non-reducing disaccharides, in which the component monosaccharides bond through anacetal linkage between theiranomeric centers. This results in neither monosaccharide being left with a hemiacetal unit that is free to act as a reducing agent.Sucrose andtrehalose 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

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The formation of a disaccharide molecule from twomonosaccharide molecules proceeds by displacing ahydroxy group from one molecule and ahydrogen nucleus (aproton) from the other, so that the new vacant bonds on the monosaccharides join the twomonomers 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 monosaccharidesglucose andgalactose, whereas the disaccharide sucrose in sugar cane and sugar beet, is a condensation product of glucose andfructose.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 complexpolysaccharides) forms what are called glycosidic bonds.[8]

Characteristic reactions

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Lactitol is one of several sugar alcohols produced from disaccharides

Disaccharides can serve asfunctional groups by forming glycosidic bonds with other organic compounds, formingglycosides andglycoconjugates.

Disaccarides characteristically undergo hydrolysis to givemonosaccharides.

Some disaccharides can behydrogenated to give usefuldisaccharide alcohols with retention of the acetal linkage. Commercial products includelactitol,isomalt, andmaltitol. Isomalt production begins with a bacterial promoted conversion of sucrose toisomaltulose.[9]

Sucrose undergoes acid catalyzed poly-dehydration to givehydroxymethylfurfural.ref>Simeonov, Svilen (2016)."Synthesis of 5-(Hydroxymethyl)furfural (HMF)".Organic Syntheses.93:29–36.doi:10.15227/orgsyn.093.0029.</ref>

Assimilation

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See also:Carbohydrate digestion

Digestion of disaccharides involves breakdown into monosaccharides.

Common disaccharides

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DisaccharideUnit 1Unit 2Bond
Sucrose (table sugar, cane sugar, beet sugar, or saccharose)GlucoseFructoseα(1→2)β
Lactose (milk sugar)GalactoseGlucoseβ(1→4)
Maltose (malt sugar)GlucoseGlucoseα(1→4)
TrehaloseGlucoseGlucoseα(1→1)α
CellobioseGlucoseGlucoseβ(1→4)
ChitobioseGlucosamineGlucosamineβ(1→4)

Maltose, cellobiose, and chitobiose arehydrolysis products of the polysaccharidesstarch,cellulose, andchitin, respectively.

Less common disaccharides include:[10]

DisaccharideUnitsBond
KojibioseTwoglucosesα(1→2)[11]
NigeroseTwo glucosesα(1→3)
IsomaltoseTwo glucosesα(1→6)
β,β-TrehaloseTwo glucosesβ(1→1)β
α,β-TrehaloseTwo glucosesα(1→1)β[12]
SophoroseTwo glucosesβ(1→2)
LaminaribioseTwo glucosesβ(1→3)
GentiobioseTwo glucosesβ(1→6)
TrehaluloseOne glucose and onefructoseα(1→1)
TuranoseOne glucose and one fructoseα(1→3)
MaltuloseOne glucose and one fructoseα(1→4)
LeucroseOne glucose and one fructoseα(1→5)
IsomaltuloseOne glucose and one fructoseα(1→6)
GentiobiuloseOne glucose and one fructoseβ(1→6)
MannobioseTwomannosesEither α(1→2), α(1→3), α(1→4), or α(1→6)
MelibioseOnegalactose and one glucoseα(1→6)
AllolactoseOne galactose and one glucoseβ(1→6)
MelibiuloseOne galactose and one fructoseα(1→6)
LactuloseOne galactose and one fructoseβ(1→4)
RutinoseOnerhamnose and one glucoseα(1→6)
RutinuloseOne rhamnose and one fructoseβ(1→6)
XylobioseTwo xylopyranosesβ(1→4)

References

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  1. ^"Biose".Merriam-Webster.
  2. ^IUPAC,Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "disaccharides".doi:10.1351/goldbook.D01776
  3. ^Liptak, Andras; Fugedi, Peter; Szurmai, Zoltan (1990).Handbook of Oligosaccharides Disaccharides. CRC-Press.ISBN 9780849329012.{{cite book}}: CS1 maint: multiple names: authors list (link)
  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 fromthe original on 2017-08-26. Retrieved2010-07-21.
  6. ^"Disaccharides and Oligosaccharides".University of Virginia Faculty and Lab Site. Archived fromthe original on 2018-11-18. Retrieved2008-01-29.
  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 fromthe original on May 12, 2013. Retrieved11 December 2013.
  9. ^Lichtenthaler, Frieder W. (2010). "Carbohydrates: Occurrence, Structures and Chemistry".Ullmann's Encyclopedia of Industrial Chemistry.doi:10.1002/14356007.a05_079.pub2.ISBN 978-3-527-30385-4.
  10. ^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.
  11. ^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.
  12. ^T. Taga; Y. Miwa; Z. Min (1997). "α,β-Trehalose Monohydrate".Acta Crystallogr. C.53 (2):234–236.Bibcode:1997AcCrC..53..234T.doi:10.1107/S0108270196012693.

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