organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...

, a tetrose 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. Chemically, monosaccharides are polyhy ...

with 4

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atoms. They have either an

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

()

functional group In organic chemistry, a functional group is any 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 r ...

in position 1 (aldotetroses) or a

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

() group in position 2 (ketotetroses). File:DErythrose Fischer.svg , D-Erythrose File:DThreose Fischer.svg , D-Threose File:DErythrulose Fischer.svg , D-Erythrulose The aldotetroses have two chiral centers ( asymmetric carbon atoms) and so 4 different

stereoisomers In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms i ...

are possible. There are two naturally occurring stereoisomers, the

enantiomers In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

erythrose Erythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and is thus part of the aldose family. The natural isomer is D-erythrose; it is a diastereomer of D -threose. Erythrose was first isolated in 1849 ...

and

threose Threose is a four-carbon monosaccharide with molecular formula C4H8O4. It has a terminal aldehyde group, rather than a ketone, in its linear chain and so is considered part of the aldose family of monosaccharides. The threose name can be used to ...

having the D

configuration Configuration or configurations may refer to: Computing * Computer configuration or system configuration * Configuration file, a software file used to configure the initial settings for a computer program * Configurator, also known as choice board ...

but not the L enantiomers. The ketotetroses have one chiral center and, therefore, two possible stereoisomers:

erythrulose D-Erythrulose (also known as erythrulose) is a tetrose carbohydrate with the chemical formula C4 H8 O4. It has one ketone group and so is part of the ketose family. It is used in some self-tanning cosmetics, in general, combined with dihydrox ...

(L- and D-form). Again, only the D enantiomer is naturally occurring.

Biological Functions

There are a few known ways that tetrose sugars are used in nature. Some are seen in metabolic pathways and others are known to affect certain enzymes.

Intermediates in the Pentose Phosphate Pathway

One of the metabolic pathways that a tetrose is involved in is the

Pentose Phosphate Pathway The pentose phosphate pathway (also called the phosphogluconate pathway and the hexose monophosphate shunt or HMP shunt) is a metabolic pathway parallel to glycolysis. It generates NADPH and pentoses (five-carbon sugars) as well as ribose 5-ph ...

. In the Pentose Phosphate Pathway, there is an oxidative stage and a non-oxidative stage. A tetrose sugar,

D-erythrose Erythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and is thus part of the aldose family. The natural isomer is D-erythrose; it is a diastereomer of D -threose. Erythrose was first isolated in 1849 ...

, is utilized in the non-oxidative stage, where D-ribulose 5-phosphate is generated into a 6 carbon sugar (

fructose 6-phosphate Fructose 6-phosphate (sometimes called the Neuberg ester) is a derivative of fructose, which has been phosphorylated at the 6-hydroxy group. It is one of several possible fructosephosphates. The β-D-form of this compound is very common in cells ...

) and a 3 carbon sugar (

glyceraldehyde 3-phosphate Glyceraldehyde 3-phosphate, also known as triose phosphate or 3-phosphoglyceraldehyde and abbreviated as G3P, GA3P, GADP, GAP, TP, GALP or PGAL, is a metabolite that occurs as an intermediate in several central pathways of all organisms.Nelson, D ...

). Both of these molecules can be used elsewhere in the body. D-erythrose 4-phosphate is generated as a product of a reaction called transaldolation. In the Pentose Phosphate Pathway, a transaldolase removes the first 3 carbon molecules of sedoheptulose 7-phosphate and places them onto a glyceraldehyde 3-phosphate. The transaldolase utilizes a

Schiff base In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure ( = alkyl or aryl, but not hydrogen). They can be considered a sub-class of imines, being either secondary ketimines or secondary aldim ...

to perform a reverse

aldol reaction The aldol reaction (aldol addition) is a Chemical reaction, reaction in organic chemistry that combines two Carbonyl group, carbonyl compounds (e.g. aldehydes or ketones) to form a new β-hydroxy carbonyl compound. Its simplest form might invol ...

and a forward aldol reaction in its mechanism, generating an erythrose 4-phosphate and

. The erythrose 4-phosphate is an important intermediate in the Pentose Phosphate Pathway because it is then used in the final non-oxidative step of the pathway. The final non-oxidative step of the pathway is a transketolase reaction. A

transketolase Transketolase (abbreviated as TK) is an enzyme that, in humans, is encoded by the ''TKT'' gene. It participates in both the pentose phosphate pathway in all organisms and the Calvin cycle of photosynthesis. Transketolase catalyzes two important r ...

utilizes a thiamine pyrophosphate, or TPP cofactor, to break the unfavorable bond between the carbon in a carbonyl and the

alpha carbon In the nomenclature of organic chemistry, a locant is a term to indicate the position of a functional group or substituent within a molecule. Numeric locants The International Union of Pure and Applied Chemistry (IUPAC) recommends the use of n ...

. TPP attacks a xylulose 5-phosphate molecule and facilitates the cleavage of the bond between the C2 (carbonyl carbon) and the C3 (alpha carbon), where glyceraldehyde 3-phosphate is released. Then, C2 can attack erythrose 4-phosphate, which forms fructose 6-phosphate. Both of the products of this reaction can enter the

gluconeogenesis Gluconeogenesis (GNG) is a metabolic pathway that results in the biosynthesis of glucose from certain non-carbohydrate carbon substrates. It is a ubiquitous process, present in plants, animals, fungi, bacteria, and other microorganisms. In verte ...

pathway to regenerate

glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...

Inhibitors of Enzymes

A tetrose diphosphate molecule, D-threose 2,4-diphosphate, was discovered to be an inhibitor of

glyceraldehyde 3-phosphate dehydrogenase Glyceraldehyde 3-phosphate dehydrogenase (abbreviated GAPDH) () is an enzyme of about 37kDa that catalyzes the sixth step of glycolysis and thus serves to break down glucose for energy and carbon molecules. In addition to this long establis ...

. Glyceraldehyde 3-phosphate dehydrogenase is the sixth enzyme used in the

glycolysis Glycolysis is the metabolic pathway that converts glucose () into pyruvic acid, pyruvate and, in most organisms, occurs in the liquid part of cells (the cytosol). The Thermodynamic free energy, free energy released in this process is used to form ...

pathway, and its function is to convert glyceraldehyde 3-phosphate into 1,3-bisphosphoglycerate. This tetrose diphosphate molecule inhibits the G3P dehydrogenase from performing catalysis because it oxidizes the enzyme by binding to it at the active site. When tetrose diphosphate is bound to the enzyme, the active site of the enzyme is blocked; therefore phosphorolysis of G3P is unable to occur. High concentrations of tetrose diphosphate must be used to outcompete the substrate, G3P, and block the function of G3P dehydrogenase. With the function of glyceraldehyde 3-phosphate dehydrogenase lost, glycolysis cannot proceed. D-erythrose 4-phosphate was found to be an inhibitor of

phosphoglucose isomerase Glucose-6-phosphate isomerase (GPI), alternatively known as phosphoglucose isomerase/phosphoglucoisomerase (PGI) or phosphohexose isomerase (PHI), is an enzyme ( ) that in humans is encoded by the ''GPI'' gene on chromosome 19. This gene enc ...

. Phosphoglucose isomerase is the second enzyme in the glycolysis pathway, and its role is to convert

glucose 6-phosphate Glucose 6-phosphate (G6P, sometimes called the Robison ester) is a glucose sugar phosphorylated at the hydroxy group on carbon 6. This dianion is very common in cells as the majority of glucose entering a cell will become phosphorylated in this w ...

into fructose 6-phosphate. In both of these cases, the tetrose is an inhibitor of an enzyme in the glycolysis pathway, preventing it from proceeding onward.

References

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