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1 Chemistry  





2 Examples of ketoses  





3 References  














Ketose






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From Wikipedia, the free encyclopedia
 


Fructose, an example of a ketose. The ketone group is the double-
bonded oxygen.

Inorganic chemistry, a ketose is a monosaccharide containing one ketone (>C=O) group per molecule.[1][2] The simplest ketose is dihydroxyacetone ((CH2OH)2C=O), which has only three carbon atoms. It is the only ketose with no optical activity. All monosaccharide ketoses are reducing sugars, because they can tautomerize into aldoses via an enediol intermediate, and the resulting aldehyde group can be oxidised, for example in the Tollens' testorBenedict's test.[3] Ketoses that are bound into glycosides, for example in the case of the fructose moietyofsucrose, are nonreducing sugars.[3]

Chemistry[edit]

Ketoses and aldoses can be chemically differentiated through Seliwanoff's test, where the sample is heated with acid and resorcinol.[4] The test relies on the dehydration reaction which occurs more quickly in ketoses, so that while aldoses react slowly, producing a light pink color, ketoses react more quickly and strongly to produce a dark red color. Ketoses can isomerize to aldoses through the Lobry-de Bruyn-van Ekenstein transformation.

Examples of ketoses[edit]

Family tree of D-ketoses up to hexoses: dihydroxyacetone (1); D-erythrulose (2); D-ribulose (3a); D-xylulose (3b); D-psicose (4a); D-fructose (4b); D-sorbose (4c); D-tagatose (4d)

All ketoses listed here are 2-ketoses, in other words, the carbonyl group is on the second carbon atom from the end:

References[edit]

  1. ^ Lindhorst, Thisbe K. (2007). Essentials of Carbohydrate Chemistry and Biochemistry (1st ed.). Wiley-VCH. ISBN 978-3-527-31528-4.
  • ^ Robyt, John F. (1997). Essentials of Carbohydrate Chemistry (1st ed.). Springer. ISBN 0-387-94951-8.
  • ^ a b McMurry, John E. (2010-01-01). Organic Chemistry: With Biological Applications. Cengage Learning. p. 880. ISBN 978-0495391449.
  • ^ "Seliwanoff's Test". Harper College. Archived from the original on 2017-12-16. Retrieved 2011-07-10.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Ketose&oldid=1215602656"

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    This page was last edited on 26 March 2024, at 02:51 (UTC).

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