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Deoxyribose, or more precisely 2-deoxyribose, is a
monosaccharide Monosaccharides (from Greek#REDIRECT Greek Greek may refer to: Greece Anything of, from, or related to Greece Greece ( el, Ελλάδα, , ), officially the Hellenic Republic, is a country located in Southeast Europe. Its population is ap ...
with idealized formula H−(C=O)−(CH2)−(CHOH)3−H. Its name indicates that it is a
deoxy sugar Deoxy sugars are sugar Sugar is the generic name for , soluble s, many of which are used in food. Simple sugars, also called s, include , , and . Compound sugars, also called s or double sugars, are molecules made of two monosaccharides ...
, meaning that it is derived from the
sugar Sugar is the generic name for sweet-tasting, soluble carbohydrate is a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosacc ...

sugar
ribose Ribose is a simple sugar and carbohydrate with molecular formula C5H10O5 and the linear-form composition H−(C=O)−(CHOH)4−H. The naturally-occurring form, , is a component of the ribonucleotides from which RNA is built, and so this compoun ...

ribose
by loss of an
oxygen Oxygen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the chemical elements In chemistry, an element is a pure substance consisting only of atoms that all have the same ...

oxygen
atom. Deoxyribose is most notable for its presence in
DNA Deoxyribonucleic acid (; DNA) is a molecule File:Pentacene on Ni(111) STM.jpg, A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five carbon rings. A molecule is an electrically neutral gro ...

DNA
. Since the pentose sugars
arabinose Arabinose is an aldopentose – a monosaccharide Monosaccharides (from Greek '' monos'': single, ''sacchar'': sugar), also called simple sugars, are the simplest form of sugar Sugar is the generic name for Sweetness, sweet-tasting, soluble ...

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.


History

Deoxyribose was discovered in 1929 by
Phoebus Levene Phoebus Aaron Theodore Levene (25 February 1869 – 6 September 1940) was an American biochemist Biochemists are scientists who are trained in biochemistry Biochemistry or biological chemistry, is the study of chemical process In a scien ...
.


Structure

Several isomers exist with the formula H−(C=O)−(CH2)−(CHOH)3−H, but in deoxyribose all the
hydroxyl A hydroxy or hydroxyl group is a functional group with the chemical formula -OH and composed of one oxygen Oxygen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the ...

hydroxyl
groups are on the same side in the
Fischer projection The Fischer projection, devised by Emil Fischer in 1891, is a two-dimensional representation of a Three-dimensional space, three-dimensional organic molecule by Graphical projection, projection. Fischer projections were originally proposed for the ...

Fischer projection
. The term "2-deoxyribose" may refer to either of two
enantiomer In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they und ...

enantiomer
s: the biologically important -2-deoxyribose and to the rarely encountered mirror image
-2-deoxyribose
-2-deoxyribose
.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. -2-deoxyribose is a precursor to the
nucleic acid Nucleic acids are biopolymer Biopolymers are natural polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecule ...

nucleic acid
DNA Deoxyribonucleic acid (; DNA) is a molecule File:Pentacene on Ni(111) STM.jpg, A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five carbon rings. A molecule is an electrically neutral gro ...

DNA
. 2-deoxyribose is an
aldopentoseIn chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they undergo ...

aldopentose
, that is, a monosaccharide with five
carbon Carbon (from la, carbo "coal") is a with the C and 6. It is lic and —making four s available to form s. It belongs to group 14 of the periodic table. Carbon makes up only about 0.025 percent of Earth's crust. Three occur naturally, ...

carbon
atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects that can be touched are ultimately composed of ato ...

atom
s and having an
aldehyde Chemically, an aldehyde is a compound containing a functional group In organic chemistry, a functional group is a substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same fu ...

aldehyde
functional group In organic chemistry, a functional group is a substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions re ...
. 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.C.Michael Hogan. 2010
''Deoxyribonucleic acid''. Encyclopedia of Earth. National Council for Science and the Environment.
eds. S.Draggan and C.Cleveland. Washington DC
The
DNA Deoxyribonucleic acid (; DNA) is a molecule File:Pentacene on Ni(111) STM.jpg, A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five carbon rings. A molecule is an electrically neutral gro ...

DNA
(deoxyribonucleic acid) molecule, which is the main repository of
genetic
genetic
information in life, consists of a long chain of deoxyribose-containing units called
nucleotides Nucleotides are organic molecules , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, ...

nucleotides
, linked via
phosphate In chemistry, a phosphate is an anion, salt (chemistry), salt, functional group or ester derived from a phosphoric acids and phosphates, phosphoric acid. It most commonly means orthophosphate, a derivative of phosphoric acid, orthophosphoric a ...

phosphate
groups. In the standard nucleic acid nomenclature, a DNA nucleotide consists of a deoxyribose molecule with an organic
base Base or BASE may refer to: Brands and enterprises * Base (mobile telephony provider), a Belgian mobile telecommunications operator *Base CRM Base CRM (originally Future Simple or PipeJump) is an enterprise software company based in Mountain Vie ...
(usually
adenine Adenine (A, Ade) is a nucleobase 230px, Pyrimidine nucleobases are simple ring molecules. Nucleobases, also known as ''nitrogenous bases'' or often simply ''bases'', are nitrogen-containing biological compounds that form nucleosides Nucleos ...

adenine
,
thymine Thymine () (symbol A symbol is a mark, sign, or word In linguistics, a word of a spoken language can be defined as the smallest sequence of phonemes that can be uttered in isolation with semantic, objective or pragmatics, practical m ...

thymine
,
guanine Guanine () (symbol A symbol is a mark, sign, or word In linguistics, a word of a spoken language can be defined as the smallest sequence of phonemes that can be uttered in isolation with semantic, objective or pragmatics, practical meaning ...

guanine
or
cytosine Cytosine () (symbol A symbol is a mark, sign, or that indicates, signifies, or is understood as representing an , , or . Symbols allow people to go beyond what is n or seen by creating linkages between otherwise very different s and s. Al ...

cytosine
) attached to the 1′ ribose carbon. The 5′ hydroxyl of each deoxyribose unit is replaced by a
phosphate In chemistry, a phosphate is an anion, salt (chemistry), salt, functional group or ester derived from a phosphoric acids and phosphates, phosphoric acid. It most commonly means orthophosphate, a derivative of phosphoric acid, orthophosphoric a ...

phosphate
(forming a
nucleotide Nucleotides are organic molecules , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, ...

nucleotide
) that is attached to the 3′ carbon of the deoxyribose in the preceding unit. The absence of the 2′
hydroxyl A hydroxy or hydroxyl group is a functional group with the chemical formula -OH and composed of one oxygen Oxygen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the ...

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 Eukaryotes () are organism In biology Biology is the natural science that studies life and living organisms, including their anatomy, physical structure, Biochemistry, chemical processes, Molecular biology, molecular interact ...

eukaryote
s) to be compactly coiled within the small
cell nucleus In cell biology, the nucleus (pl. ''nuclei''; from Latin or , meaning ''kernel'' or ''seed'') is a biological membrane#Function, membrane-bound organelle found in eukaryote, eukaryotic cell (biology), cells. Eukaryotes usually have a single n ...

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 Ribose 5-phosphate (R5P) is both a product and an intermediate of the pentose phosphate pathway The pentose phosphate pathway (also called the phosphogluconate pathway and the hexose monophosphate shunt) is a metabolic pathway In biochemistry ...

ribose 5-phosphate
by enzymes called
ribonucleotide reductase Ribonucleotide reductase (RNR), also known as ribonucleotide diphosphate reductase (rNDP), is an enzyme that catalyzes the formation of deoxyribonucleotides from ribonucleotides. It catalyzes this formation by removing the 2'-hydroxyl group of the ...
s. These enzymes catalyse the deoxygenation process.


References

{{Carbohydrates Aldopentoses Deoxy sugars 1929 in biology