Deoxyribose, or more precisely2-deoxyribose, is amonosaccharide with idealized formula H−(C=O)−(CH2)−(CHOH)3−H. Its name indicates that it is adeoxy sugar, meaning that it is derived from thesugarribose by loss of ahydroxy group. Discovered in 1929 byPhoebus Levene,[4] deoxyribose is most notable for its presence inDNA. Since the pentose sugarsarabinose 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.
Several isomers exist with the formula H−(C=O)−(CH2)−(CHOH)3−H, but in deoxyribose all thehydroxyl groups are on the same side in theFischer projection. The term "2-deoxyribose" may refer to either of twoenantiomers: the biologically importantd-2-deoxyribose and to the rarely encountered mirror imagel-2-deoxyribose.[5]d-2-deoxyribose is a precursor to thenucleic acidDNA. 2-deoxyribose is analdopentose, that is, a monosaccharide with fivecarbonatoms and having analdehydefunctional 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).
As a component of DNA, 2-deoxyribose derivatives have an important role in biology.[6] TheDNA (deoxyribonucleic acid) molecule, which is the main repository ofgenetic information in life, consists of a long chain of deoxyribose-containing units callednucleotides, linked viaphosphate groups. In the standardnucleic acid nomenclature, a DNA nucleotide consists of a deoxyribose molecule with an organicbase (usuallyadenine,thymine,guanine orcytosine) attached to the 1′ ribose carbon. The 5′ hydroxyl of each deoxyribose unit is replaced by aphosphate (forming anucleotide) 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 compared to RNA, which allows it to assume the double-helix conformation, and also (in theeukaryotes) to be compactly coiled within the smallcell nucleus. The double-stranded DNA molecules are also typically much longer than RNA molecules. The backbone of RNA and 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.
In one study, deoxyribose was shown to have pro-angiogenic properties when applied topically in a gel to wounds in rats.[7] In addition, this topical gel also increasedVascular Endothelial Growth Factor (VEGF), which has been implicated in hair growth.[8] This could potentially lead to future products to treat hair loss in humans.
^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.
^Serkan Dikici, Yar, M., Bullock, A. J., Shepherd, J., Roman, S., & MacNeil, S. (2021). Developing Wound Dressings Using 2-deoxy-D-Ribose to Induce Angiogenesis as a Backdoor Route for Stimulating the Production of Vascular Endothelial Growth Factor. International Journal of Molecular Sciences, 22(21), 11437–11437.https://doi.org/10.3390/ijms222111437
^Yano, K., Brown, L. F., & Detmar, M. (2001). Control of hair growth and follicle size by VEGF-mediated angiogenesis. Journal of Clinical Investigation, 107(4), 409–417.https://doi.org/10.1172/jci11317
