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β-D-2-deoxyribose

File:D-dexoyribose_chain.svg · Wikimedia Commons · See Wikimedia Commons

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β-D-2-deoxyribose

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Also known as 2-deoxy-D-ribose, 2-deoxy-D-erythro-pentose, thyminose, 2-deoxy-beta-D-ribofuranose

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, 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.

AI overview

β-D-2-deoxyribose is a five-carbon sugar that forms one of the essential building blocks of DNA, discovered in 1929 by Phoebus Levene. It is created by removing a hydroxy group from the sugar ribose, which is why it bears the name "deoxy" (meaning lacking oxygen).

AI-generated from the Wikipedia summary — may contain errors.

Chemical data

Formula
C5H10O4
Molecular weight
134.13 g/mol
IUPAC name
(2R,4S,5R)-5-(hydroxymethyl)oxolane-2,4-diol
SMILES
C1[C@@H]([C@H](O[C@H]1O)CO)O
InChIKey
PDWIQYODPROSQH-VPENINKCSA-N
XLogP
-1
Polar surface area
69.9 Ų
H-bond donors
3
H-bond acceptors
4
Formal charge
0

via PubChem

~3 min read

Encyclopedic overview

5 sections
Contents
  • Structure
  • Biological importance
  • Biosynthesis
  • Angiogenesis
  • References

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, 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 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 -2-deoxyribose and to the rarely encountered mirror image -2-deoxyribose. -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.

Excerpted from Wikipedia’s “β-D-2-deoxyribose” article, available under the CC BY-SA 4.0 licence.

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