Editing Deoxyribose

{{about|the naturally occurring {{sm|d}}-form of deoxyribose|the {{sm|l}}-form|L-deoxyribose}}
{{chembox
| Watchedfields  = changed
| verifiedrevid  = 443568548
| Name           = {{sm|d}}-deoxyribose
| ImageFileL1    = D-dexoyribose chain.svg
| ImageClassL1   = skin-invert-image
| ImageFileR1    = D-Deoxyribose.png
| ImageClassR1   = skin-invert-image
| ImageFileL2    = D-deoxyribose_chain-3D-balls.png
| ImageClassL2   = bg-transparent
| ImageFileR2    = D-deoxyribose-3D-balls.png
| ImageClassR2   = bg-transparent
| IUPACName      = 2-Deoxy-{{sm|d}}-ribose<ref>https://iupac.qmul.ac.uk/2carb/13.html</ref>
| SystematicName = 2-Deoxy-{{sm|d}}-''erythro''-pentose<ref>https://iupac.qmul.ac.uk/2carb/13.html</ref>
| OtherNames     = ''aldehydo''-2-Deoxy-{{sm|d}}-ribose<br/>Thyminose
| Section1       = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4573703
| InChI = 1/C5H10O4/c6-2-1-4(8)5(9)3-7/h2,4-5,7-9H,1,3H2/t4-,5+/m0/s1
| InChIKey = ASJSAQIRZKANQN-CRCLSJGQBK
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H10O4/c6-2-1-4(8)5(9)3-7/h2,4-5,7-9H,1,3H2/t4-,5+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ASJSAQIRZKANQN-CRCLSJGQSA-N
| CASNo = 533-67-5
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = LSW4H01241
| EC_number = 208-573-0
| PubChem = 5460005
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28816
| SMILES = C(C=O)[C@@H]([C@@H](CO)O)O
}}
| Section2       = {{Chembox Properties
| Properties_ref =<ref>{{Merck11th|2890}}</ref>
| C=5 | H=10 | O=4
| Appearance = White solid
| Density =
| MeltingPtC = 91
| Solubility = Very soluble
  }}
| Section7       = {{Chembox Hazards
| FlashPt =
  }}
}}

'''Deoxyribose''', or more precisely '''2-deoxyribose''', is a [[monosaccharide]] with idealized formula H−(C=O)−(CH<sub>2</sub>)−(CHOH)<sub>3</sub>−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]],<ref name="levene">{{cite web |title=Comprehensive Timeline of Biological Discoveries |url=https://dvd.ambrosevideo.com/resources/documents/Comprehensive%20Timeline%20of%20Biological%20Discoveries.pdf |access-date=31 July 2017 |archive-date=10 September 2016 |archive-url=https://web.archive.org/web/20160910083309/http://dvd.ambrosevideo.com/resources/documents/Comprehensive%20Timeline%20of%20Biological%20Discoveries.pdf |url-status=dead }}</ref> 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)−(CH<sub>2</sub>)−(CHOH)<sub>3</sub>−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 [[enantiomer]]s: the biologically important {{sm|d}}-2-deoxyribose and to the rarely encountered mirror image [[L-Deoxyribose|{{sm|l}}-2-deoxyribose]].<ref name=moens>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.</ref> {{sm|d}}-2-deoxyribose is a precursor to the [[nucleic acid]] [[DNA]]. 2-deoxyribose is an [[aldopentose]], that is, a monosaccharide with five [[carbon]] [[atom]]s and having an [[aldehyde]] [[functional group]].

In aqueous solution, deoxyribose primarily exists as a mixture of three structures: the linear form H−(C=O)−(CH<sub>2</sub>)−(CHOH)<sub>3</sub>−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). 
[[Image:Deoxyribose forms.svg|thumb|center|400px|Chemical equilibrium of deoxyribose in solution]]

== Biological importance ==
As a component of DNA, 2-deoxyribose derivatives have an important role in biology.<ref>C.Michael Hogan. 2010. [http://www.eoearth.org/articles/view/158858/?topic=49496 ''Deoxyribonucleic acid''. Encyclopedia of Earth. National Council for Science and the Environment.] eds. S.Draggan and C.Cleveland. Washington DC</ref> The [[DNA]] (deoxyribonucleic acid) molecule, which is the main repository of [[genetics|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 (chemistry)|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 compared to RNA, which allows it to assume the double-helix conformation, and also (in the [[eukaryote]]s) 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 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===
Deoxyribose is generated from [[ribose 5-phosphate]] by enzymes called [[ribonucleotide reductase]]s.  These enzymes catalyse the deoxygenation process.

===Angiogenesis===
In one study, deoxyribose was shown to have pro-[[angiogenic]] properties when applied topically in a gel to wounds in rats.<ref>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</ref> In addition, this topical gel also increased [[Vascular Endothelial Growth Factor]] (VEGF), which has been implicated in hair growth.<ref>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</ref> This could potentially lead to future products to treat hair loss in humans.

==References==
{{wiktionary|deoxyribose|desoxyribose}}
{{reflist}}

{{Carbohydrates}}

[[Category:Aldopentoses]]
[[Category:Deoxy sugars]]
[[Category:1929 in biology]]
[[Category:Furanoses]]
[[Category:Pyranoses]]