chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions ...

, a pentose is a

monosaccharide Monosaccharides (from Greek ''monos'': single, '' sacchar'': sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. They are usually colorless, water-solub ...

(simple sugar) with five carbon atoms. The chemical formula of many pentoses is , and their molecular weight is 150.13 g/mol.-Ribose
. PubChem compound webpage, accessed on 2010-02-06. Pentoses are very important in biochemistry. Ribose is a constituent of

RNA Ribonucleic acid (RNA) is a polymeric molecule essential in various biological roles in coding, decoding, regulation and expression of genes. RNA and deoxyribonucleic acid ( DNA) are nucleic acids. Along with lipids, proteins, and carbohydra ...

nucleic acid Nucleic acids are biopolymers, macromolecules, essential to all known forms of life. They are composed of nucleotides, which are the monomers made of three components: a 5-carbon sugar, a phosphate group and a nitrogenous base. The two main cl ...

s, and erythrose 4-phosphate (E4P), which is used in the synthesis of aromatic

amino acids Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha am ...

. Like some other monosaccharides, pentoses exist in two forms, open-chain (linear) or closed-chain (cyclic), that easily convert into each other in water solutions. The linear form of a pentose, which usually exists only in solutions, has an open-chain backbone of five carbons. Four of these carbons have one hydroxyl functional group (–OH) each, connected by a single bond, and one has an oxygen atom connected by a double bond (=O), forming a carbonyl group (C=O). The remaining bonds of the carbon atoms are satisfied by six hydrogen atoms. Thus the structure of the linear form is H–(CHOH)_''x''–C(=O)–(CHOH)_4-''x''–H, where ''x'' is 0, 1, or 2. The term "pentose" sometimes is assumed to include deoxypentoses, such as deoxyribose: compounds with general formula that can be described as derived from pentoses by replacement of one or more hydroxyl groups with hydrogen atoms.

Classification

The

aldopentose In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is , and their molecular weight is 150.13 g/mol.aldehyde derivative with structure H–C(=O)–(CHOH)₄–H. The most important example is ribose. The ketopentoses instead have the carbonyl at positions 2 or 3, forming a

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

derivative with structure H–CHOH–C(=O)–(CHOH)₃–H (2-ketopentose) or H–(CHOH)₂–C(=O)–(CHOH)₂–H (3-ketopentose). The latter is not known to occur in nature and are difficult to synthesize. In the open form, there are eight aldopentoses and four 2-ketopentoses, stereoisomers that differ in the spatial position of the hydroxyl groups. These forms occur in pairs of optical isomers, generally labelled "" or "" by conventional rules (independently of their

optical activity Optical rotation, also known as polarization rotation or circular birefringence, is the rotation of the orientation of the plane of polarization about the optical axis of linearly polarized light as it travels through certain materials. Circul ...

Aldopentoses

The aldopentoses have three

chiral center In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups cr ...

s; therefore, eight (2³) different stereoisomers are possible. Ribose is a constituent of

, and the related molecule, deoxyribose, is a constituent of DNA. Phosphorylated pentoses are important products of the pentose phosphate pathway, most importantly ribose 5-phosphate (R5P), which is used in the synthesis of nucleotides and nucleic acids, and erythrose 4-phosphate (E4P), which is used in the synthesis of aromatic amino acids.

Ketopentoses

The 2-ketopentoses have two chiral centers; therefore, four (2²) different stereoisomers are possible. The 3-ketopentoses are rare.

Cyclic form

The closed or cyclic form of a pentose is created when the carbonyl group interacts with a hydroxyl in another carbon, turning the carbonyl into a hydroxyl and creating an ether bridge –O– between the two carbons. This

intramolecular reaction Intramolecular in chemistry describes a process or characteristic limited within the structure of a single molecule, a property or phenomenon limited to the extent of a single molecule. Examples * intramolecular hydride transfer (transfer of a hy ...

yields a cyclic molecule, with a ring consisting of one oxygen atom and usually four carbon atoms; the cyclic compounds are then called furanoses, for having the same rings as the cyclic ether tetrahydrofuran. Library of Congress catalog 66-25695 The closure turns the carboxyl carbon into a

, which may have any of two configurations, depending on the position of the new hydroxyl. Therefore, each linear form can produce two distinct closed forms, identified by prefixes "α" and "β".

Deoxypentoses

The one deoxypentose has two total stereoisomers.

Properties

In the cell, pentoses have a higher

metabolic Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...

stability than hexoses. A polymer composed of pentose sugars is called a

pentosan Pentosans are polymers composed of pentoses. In contrast to cellulose, which is composed of hexose (glucose) monomers, pentosans are derived from five-carbon sugars such as xylose. Pentosan-rich biomass is the precursor to furfural. The pentosan co ...

Tests for pentoses

The most important tests for pentoses rely on converting the pentose to furfural, which then reacts with a

chromophore A chromophore is the part of a molecule responsible for its color. The color that is seen by our eyes is the one not absorbed by the reflecting object within a certain wavelength spectrum of visible light. The chromophore is a region in the molec ...

. In Tollens’ test for pentoses (not to be confused with Tollens' silver-mirror test for reducing sugars), the

furfural Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occurs ...

ring reacts with phloroglucinol to produce a colored compound; in the

aniline acetate test The aniline acetate test is a chemical test for the presence of certain carbohydrates, in which they are converted to furfural with hydrochloric acid, which reacts with aniline acetate to produce a bright pink color. Pentoses give a strong reacti ...

with aniline acetate; and in Bial's test, with orcinol. In each of these tests, pentoses react much more strongly and quickly than hexoses.

References

{{carbohydrates