This article is about the naturally occurring d-form of deoxyribose. For the l-form, see L-deoxyribose.
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 sugarribose 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.
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 acidDNA. 2-deoxyribose is an aldopentose, that is, a monosaccharide with five carbonatoms and having an aldehydefunctional 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 importanceedit
As a component of DNA, 2-deoxyribose derivatives have an important role in biology.[4] 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 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 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.
^(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
February 15, 2024
deoxyribose, this, article, about, naturally, occurring, form, deoxyribose, form, deoxyribose, more, precisely, deoxyribose, monosaccharide, with, idealized, formula, choh, name, indicates, that, deoxy, sugar, meaning, that, derived, from, sugar, ribose, loss,. This article is about the naturally occurring d form of deoxyribose For the l form see L deoxyribose 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 d deoxyribose NamesIUPAC name 2 deoxy d riboseOther names 2 deoxy d erythro pentosethyminoseIdentifiersCAS Number 533 67 5 Y3D model JSmol Interactive imageChEBI CHEBI 28816 YChemSpider 4573703 YEC Number 208 573 0PubChem CID 5460005UNII LSW4H01241 YCompTox Dashboard EPA DTXSID60190259InChI InChI 1S C5H10O4 c6 2 1 4 8 5 9 3 7 h2 4 5 7 9H 1 3H2 t4 5 m0 s1 YKey ASJSAQIRZKANQN CRCLSJGQSA N YInChI 1 C5H10O4 c6 2 1 4 8 5 9 3 7 h2 4 5 7 9H 1 3H2 t4 5 m0 s1Key ASJSAQIRZKANQN CRCLSJGQBKSMILES C C O C H C H CO O OProperties 1 Chemical formula C 5H 10O 4Molar mass 134 131 g mol 1Appearance White solidMelting point 91 C 196 F 364 K Solubility in water Very solubleExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Structure 2 Biological importance 2 1 Biosynthesis 3 ReferencesStructure editSeveral 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 nbsp Chemical equilibrium of deoxyribose in solutionBiological importance editAs a component of DNA 2 deoxyribose derivatives have an important role in biology 4 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 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 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 edit Deoxyribose is generated from ribose 5 phosphate by enzymes called ribonucleotide reductases These enzymes catalyse the deoxygenation process References edit nbsp 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 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 Retrieved from https en wikipedia org w index php title Deoxyribose amp oldid 1199511963, wikipedia, wiki, book, books, library,
