Deoxyribose, or more precisely 2-deoxyribose, is a monosaccharide with
idealized formula H−(C=O)−(CH2)−(CHOH)3−H. Its name indicates
that it is a deoxy sugar, meaning that it is derived from the sugar
ribose by loss of an oxygen atom. Since the pentose sugars arabinose
and ribose only differ by the stereochemistry at C2′, 2-deoxyribose
and 2-deoxyarabinose are equivalent, although the latter term is
rarely used because ribose, not arabinose, is the precursor to
3 Biological importance
Deoxyribose was discovered in 1929 by Phoebus Levene.
Several isomers exist with the formula
H−(C=O)−(CH2)−(CHOH)3−H, but in deoxyribose all the hydroxyl
groups are on the same side in the Fischer projection. The term
"2-deoxyribose" may refer to either of two enantiomers: the
biologically important D-2-deoxyribose and to the rarely encountered
mirror image L-2-deoxyribose. D-2-deoxyribose is a precursor to the
nucleic acid DNA. 2-deoxyribose is an aldopentose, that is, a
monosaccharide with five carbon atoms and having an aldehyde
In aqueous solution, deoxyribose primarily exists as a mixture of
three structures: the linear form H−(C=O)−(CH2)−(CHOH)3−H and
two ring forms, deoxyribofuranose ("C3′-endo"), with a five-membered
ring, and deoxyribopyranose ("C2′-endo"), with a six-membered ring.
The latter form is predominant (whereas the C3′-endo form is favored
Chemical equilibrium of deoxyribose in solution
As a component of DNA, 2-deoxyribose derivatives have an important
role in biology. The
DNA (deoxyribonucleic acid) molecule, which is
the main repository of genetic information in life, consists of a long
chain of deoxyribose-containing units called nucleotides, linked via
phosphate groups. In the standard nucleic acid nomenclature, a DNA
nucleotide consists of a deoxyribose molecule with an organic base
(usually adenine, thymine, guanine or cytosine) attached to the 1′
ribose carbon. The 5′ hydroxyl of each deoxyribose unit is replaced
by a phosphate (forming a nucleotide) that is attached to the 3′
carbon of the deoxyribose in the preceding unit.
The absence of the 2′ hydroxyl group in deoxyribose is apparently
responsible for the increased mechanical flexibility of
to RNA, which allows it to assume the double-helix conformation, and
also (in the eukaryotes) to be compactly coiled within the small cell
nucleus. The double-stranded
DNA molecules are also typically much
longer than RNA molecules. The backbone of RNA and
structurally similar, but RNA is single stranded, and made from ribose
as opposed to deoxyribose.
Other biologically important derivatives of deoxyribose include mono-,
di-, and triphosphates, as well as 3′-5′ cyclic monophosphates.
Deoxyribose is generated from ribose 5-phosphate by enzymes called
ribonucleotide reductases. These enzymes catalyse the deoxygenation
Look up deoxyribose or desoxyribose in Wiktionary, the free
^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and
Biologicals (11th ed.), Merck, 1989, ISBN 091191028X , 2890
^ "Comprehensive Timeline of Biological Discoveries" (PDF). Retrieved
31 July 2017.
^ C Bernelot-Moens and B Demple (1989), Multiple
DNA repair activities
for 3′-deoxyribose fragments in Escherichia coli. Nucleic Acids
Research, Volume 17, issue 2, p. 587–600.
^ C.Michael Hogan. 2010. Deoxyribonucleic acid. Encyclopedia of Earth.
National Council for Science and the Environment. eds. S.Draggan and
C.Cleveland. Washington DC
Types of carbohydrates
Dextrin / Dextran
Fructose / Fructan
Galactose / Galactan
Glucose / Glucan
Levan beta 2→6