Deoxyribose
| |||
| |||
Names | |||
---|---|---|---|
IUPAC name
2-deoxy-d-ribose
| |||
Other names
2-deoxy-d-erythro-pentose
thyminose | |||
Identifiers | |||
3D model (
JSmol ) |
|||
ChEBI | |||
ChemSpider | |||
EC Number |
| ||
PubChem CID
|
|||
UNII | |||
CompTox Dashboard (EPA)
|
|||
| |||
| |||
Properties[1] | |||
C5H10O4 | |||
Molar mass | 134.131 g·mol−1 | ||
Appearance | White solid | ||
Melting point | 91 °C (196 °F; 364 K) | ||
Very soluble | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
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 a hydroxy group. Discovered in 1929 by Phoebus Levene,[2] deoxyribose is most notable for its presence in DNA. 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.
Structure
Several isomers exist with the formula H−(C=O)−(CH2)−(CHOH)3−H, but in deoxyribose all the
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).
Biological importance
As a component of DNA, 2-deoxyribose derivatives have an important role in biology.) that is attached to the 3′ carbon of the deoxyribose in the preceding unit.
The absence of the 2′
Other biologically important derivatives of deoxyribose include mono-, di-, and triphosphates, as well as 3′-5′ cyclic monophosphates.
Biosynthesis
Deoxyribose is generated from ribose 5-phosphate by enzymes called ribonucleotide reductases. These enzymes catalyse the deoxygenation process.
References
- ISBN 091191028X, 2890
- ^ "Comprehensive Timeline of Biological Discoveries" (PDF). Archived from the original (PDF) on 10 September 2016. 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