Ribose
Encyclopedia
Ribose is an organic compound
with the formula C5H10O5; specifically, a monosaccharide
(simple sugar
) with linear form H–(C=O)–(CHOH)4–H, which has all the hydroxyl
groups on the same side in the Fischer projection
.
The term may refer to any of two enantiomer
s: almost always to D-ribose, which occurs widely in nature and is discussed here; or to its synthetic mirror image L-ribose, which is not found in nature and is of limited interest.
D-Ribose was first reported in 1891 by Emil Fischer
. It is a C'-2 carbon enantiomer of the sugar D-arabinose
(both isomers of which are named for their source, gum arabic) and ribose itself is named as a transposition of the name of arabinose.
Ribose comprises the backbone of RNA
, a biopolymer
that is the basis of genetic transcription
. It is related to deoxyribose
, as found in DNA
. Once phosphorylated, ribose can become a subunit of ATP
, NADH, and several other compounds that are critical to metabolism
like the secondary messengers cAMP
and cGMP
.
atoms that, in its open chain
form, has an aldehyde
functional group
at one end. In the conventional numbering scheme for monosaccharides, the carbon atoms are numbered from C1' (in the aldehyde group) to C5'. The deoxyribose
derivative, found in DNA, differs from ribose by having a hydrogen
atom in place of the hydroxyl
group in carbon C2'.
Like many monosaccharides, ribose occurs in water as the linear form H–(C=O)–(CHOH)4–H and any of two ring forms: ribofuranose ("C3'-endo"), with a five-membered ring, and ribopyranose ("C2'-endo"), with a six-membered ring. The ribofuranose form is predominant in aqueous solution
.
The "D-" in the name D-ribose refers to the stereochemistry
of the chiral
carbon atom farthest away from the aldehyde group (C4'). In D-ribose, as in all D-sugars, this carbon atom has the same configuration as in D-glyceraldehyde.
catalyzes this reaction by converting D-ribose to D-ribose 5-phosphate
. Once converted, D-ribose-5-phosphate is available for the manufacturing of the amino acids tryptophan
and histidine
, or for use in the pentose phosphate pathway
. The absorption of D-ribose is 88–100% in the small intestines (up to 200 mg/kg/hr).
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with the formula C5H10O5; specifically, a monosaccharide
Monosaccharide
Monosaccharides are the most basic units of biologically important carbohydrates. They are the simplest form of sugar and are usually colorless, water-soluble, crystalline solids. Some monosaccharides have a sweet taste. Examples of monosaccharides include glucose , fructose , galactose, xylose...
(simple sugar
Sugar
Sugar is a class of edible crystalline carbohydrates, mainly sucrose, lactose, and fructose, characterized by a sweet flavor.Sucrose in its refined form primarily comes from sugar cane and sugar beet...
) with linear form H–(C=O)–(CHOH)4–H, which has all the hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
groups on the same side in the Fischer projection
Fischer projection
The Fischer projection, devised by Hermann Emil Fischer in 1891, is a two-dimensional representation of a three-dimensional organic molecule by projection. Fischer projections were originally proposed for the depiction of carbohydrates and used by chemists, particularly in organic chemistry and...
.
The term may refer to any of two enantiomer
Enantiomer
In chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable , much as one's left and right hands are the same except for opposite orientation. It can be clearly understood if you try to place your hands one over the other without...
s: almost always to D-ribose, which occurs widely in nature and is discussed here; or to its synthetic mirror image L-ribose, which is not found in nature and is of limited interest.
D-Ribose was first reported in 1891 by Emil Fischer
Hermann Emil Fischer
Hermann Emil Fischer, Emil Fischer was a German chemist and 1902 recipient of the Nobel Prize in Chemistry. He discovered the Fischer esterification. He developed the Fischer projection, a symbolic way of drawing asymmetric carbon atoms.-Early years:Fischer was born in Euskirchen, near Cologne,...
. It is a C'-2 carbon enantiomer of the sugar D-arabinose
Arabinose
Arabinose is an aldopentose – a monosaccharide containing five carbon atoms, and including an aldehyde functional group.For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, or structurally analogous to D-glyceraldehyde.For sugars, the D/L...
(both isomers of which are named for their source, gum arabic) and ribose itself is named as a transposition of the name of arabinose.
Ribose comprises the backbone of RNA
RNA
Ribonucleic acid , or RNA, is one of the three major macromolecules that are essential for all known forms of life....
, a biopolymer
Biopolymer
Biopolymers are polymers produced by living organisms. Since they are polymers, Biopolymers contain monomeric units that are covalently bonded to form larger structures. There are three main classes of biopolymers based on the differing monomeric units used and the structure of the biopolymer formed...
that is the basis of genetic transcription
Transcription (genetics)
Transcription is the process of creating a complementary RNA copy of a sequence of DNA. Both RNA and DNA are nucleic acids, which use base pairs of nucleotides as a complementary language that can be converted back and forth from DNA to RNA by the action of the correct enzymes...
. It is related to deoxyribose
Deoxyribose
Deoxyribose, more, precisely 2-deoxyribose, is a monosaccharide with idealized formula H---3-H. Its name indicates that it is a deoxy sugar, meaning that it is derived from the sugar ribose by loss of an oxygen atom...
, as found in DNA
DNA
Deoxyribonucleic acid is a nucleic acid that contains the genetic instructions used in the development and functioning of all known living organisms . The DNA segments that carry this genetic information are called genes, but other DNA sequences have structural purposes, or are involved in...
. Once phosphorylated, ribose can become a subunit of ATP
Adenosine triphosphate
Adenosine-5'-triphosphate is a multifunctional nucleoside triphosphate used in cells as a coenzyme. It is often called the "molecular unit of currency" of intracellular energy transfer. ATP transports chemical energy within cells for metabolism...
, NADH, and several other compounds that are critical to metabolism
Metabolism
Metabolism is the set of chemical reactions that happen in the cells of living organisms to sustain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments. Metabolism is usually divided into two categories...
like the secondary messengers cAMP
Cyclic adenosine monophosphate
Cyclic adenosine monophosphate is a second messenger important in many biological processes...
and cGMP
Cyclic guanosine monophosphate
Cyclic guanosine monophosphate is a cyclic nucleotide derived from guanosine triphosphate . cGMP acts as a second messenger much like cyclic AMP...
.
Structure
Ribose is an aldopentose, that is a monosaccharide containing five carbonCarbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
atoms that, in its open chain
Open chain
In chemistry, an open-chain compound or acyclic compound is a compound with a linear structure, rather than a cyclic one....
form, has an aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
functional group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
at one end. In the conventional numbering scheme for monosaccharides, the carbon atoms are numbered from C1' (in the aldehyde group) to C5'. The deoxyribose
Deoxyribose
Deoxyribose, more, precisely 2-deoxyribose, is a monosaccharide with idealized formula H---3-H. Its name indicates that it is a deoxy sugar, meaning that it is derived from the sugar ribose by loss of an oxygen atom...
derivative, found in DNA, differs from ribose by having a hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
atom in place of the hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
group in carbon C2'.
Like many monosaccharides, ribose occurs in water as the linear form H–(C=O)–(CHOH)4–H and any of two ring forms: ribofuranose ("C3'-endo"), with a five-membered ring, and ribopyranose ("C2'-endo"), with a six-membered ring. The ribofuranose form is predominant in aqueous solution
Aqueous solution
An aqueous solution is a solution in which the solvent is water. It is usually shown in chemical equations by appending aq to the relevant formula, such as NaCl. The word aqueous means pertaining to, related to, similar to, or dissolved in water...
.
The "D-" in the name D-ribose refers to the stereochemistry
Stereochemistry
Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms within molecules. An important branch of stereochemistry is the study of chiral molecules....
of the chiral
Chirality (chemistry)
A chiral molecule is a type of molecule that lacks an internal plane of symmetry and thus has a non-superimposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom....
carbon atom farthest away from the aldehyde group (C4'). In D-ribose, as in all D-sugars, this carbon atom has the same configuration as in D-glyceraldehyde.
Phosphorylation
In biology, D-ribose must be phosphorylated by the cell before it can be used. RibokinaseRibokinase
In enzymology, a ribokinase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are ATP and D-ribose, whereas its two products are ADP and D-ribose 5-phosphate....
catalyzes this reaction by converting D-ribose to D-ribose 5-phosphate
Ribose 5-phosphate
Ribose 5-phosphate is both a product and an intermediate of the pentose phosphate pathway. The last step of the oxidative reactions in the pentose phosphate pathway is the production of ribulose-5-phosphate. Depending on the body's state, ribulose-5-phosphate can reversibly isomerize to...
. Once converted, D-ribose-5-phosphate is available for the manufacturing of the amino acids tryptophan
Tryptophan
Tryptophan is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG...
and histidine
Histidine
Histidine Histidine, an essential amino acid, has a positively charged imidazole functional group. It is one of the 22 proteinogenic amino acids. Its codons are CAU and CAC. Histidine was first isolated by German physician Albrecht Kossel in 1896. Histidine is an essential amino acid in humans...
, or for use in the pentose phosphate pathway
Pentose phosphate pathway
The pentose phosphate pathway is a process that generates NADPH and pentoses . There are two distinct phases in the pathway. The first is the oxidative phase, in which NADPH is generated, and the second is the non-oxidative synthesis of 5-carbon sugars...
. The absorption of D-ribose is 88–100% in the small intestines (up to 200 mg/kg/hr).