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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 deoxyribose.

Contents

1 History 2 Structure 3 Biological importance

3.1 Biosynthesis

4 References

History[edit] Deoxyribose
Deoxyribose
was discovered in 1929 by Phoebus Levene.[2] Structure[edit] 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.[3] 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 functional group. 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 for ribose).

Chemical equilibrium of deoxyribose in solution

Biological importance[edit] As a component of DNA, 2-deoxyribose derivatives have an important role in biology.[4] The DNA
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 DNA
DNA
compared 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
DNA
molecules are also typically much longer than RNA molecules. The backbone of RNA and DNA
DNA
are 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. Biosynthesis[edit] Deoxyribose
Deoxyribose
is generated from ribose 5-phosphate by enzymes called ribonucleotide reductases. These enzymes catalyse the deoxygenation process. References[edit]

Look up deoxyribose or desoxyribose in Wiktionary, the free dictionary.

^ 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
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

v t e

Types of carbohydrates

General

Aldose Ketose Furanose Pyranose

Geometry

Anomer Cyclohexane conformation Mutarotation

Monosaccharides

Dioses

Aldodiose

Glycolaldehyde

Trioses

Aldotriose

Glyceraldehyde

Ketotriose

Dihydroxyacetone

Tetroses

Aldotetroses

Erythrose Threose

Ketotetrose

Erythrulose

Pentoses

Aldopentoses

Arabinose Lyxose Ribose Xylose

Ketopentoses

Ribulose Xylulose

Deoxy sugars

Deoxyribose

Hexoses

Aldohexoses

Allose Altrose Galactose Glucose Gulose Idose Mannose Talose

Ketohexoses

Fructose Psicose Sorbose Tagatose

Deoxy sugars

Fucose Fuculose Rhamnose

Heptoses

Ketoheptoses

Mannoheptulose Sedoheptulose

Above 7

Octoses Nonoses

Neuraminic acid

Multiple

Disaccharides

Cellobiose Isomaltose Isomaltulose Lactose Lactulose Maltose Sucrose Trehalose Turanose

Trisaccharides

Maltotriose Melezitose Raffinose

Tetrasaccharides

Stachyose

Other oligosaccharides

Acarbose Fructooligosaccharide (FOS) Galactooligosaccharide
Galactooligosaccharide
(GOS) Isomaltooligosaccharide (IMO) Maltodextrin Mannan-oligosaccharides (MOS)

Polysaccharides

Beta-glucan

Oat beta-glucan Lentinan Sizofiran Zymosan Cellulose Chitin

Chitosan Dextrin
Dextrin
/ Dextran Fructose
Fructose
/ Fructan

Inulin

Galactose
Galactose
/ Galactan Glucose
Glucose
/ Glucan

Glycogen

Hemicellulose Levan beta 2→6 Lignin Mannan Pectin Starch

Amylopectin Amylose

.