Sugar phosphates (

sugars Sugar is the generic name for Sweetness, sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides ...

that have added or substituted

phosphate Phosphates are the naturally occurring form of the element phosphorus. In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthop ...

groups) are often used in biological systems to store or transfer

energy Energy () is the physical quantity, quantitative physical property, property that is transferred to a physical body, body or to a physical system, recognizable in the performance of Work (thermodynamics), work and in the form of heat and l ...

. They also form the backbone for

DNA Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...

and

RNA Ribonucleic acid (RNA) is a polymeric molecule that is essential for most biological functions, either by performing the function itself (non-coding RNA) or by forming a template for the production of proteins (messenger RNA). RNA and deoxyrib ...

. Sugar phosphate backbone geometry is altered in the vicinity of the modified nucleotides. Examples include: *

Dihydroxyacetone phosphate Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is the anion with the formula HOCH2C(O)CH2OPO32-. This anion is involved in many metabolic pathways, including the Calvin cycle in plants and glycolysis.Nelson, D. L.; Co ...

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 wa ...

Phytic acid Phytic acid is a six-fold dihydrogenphosphate ester of inositol (specifically, of the ''myo'' isomer), also called inositol hexaphosphate, inositol hexakisphosphate (IP6) or inositol polyphosphate. At physiological pH, the phosphates are partia ...

* Teichoic acid

Electronic structure of the sugar-phosphate backbone

The sugar-phosphate backbone has

multiplex Multiplex may refer to: Science and technology * Multiplex communication, combining many signals into one transmission circuit or channel ** Multiplex (television), a group of digital television or radio channels that are combined for broadcast * ...

electronic structure and the electron

delocalisation In chemistry, delocalized electrons are electrons in a molecule, ion or solid metal that are not associated with a single atom or a covalent bond.IUPAC Gold Boo''delocalization''/ref> The term delocalization is general and can have slightly diff ...

complicates its

theoretical A theory is a systematic and rational form of abstract thinking about a phenomenon, or the conclusions derived from such thinking. It involves contemplative and logical reasoning, often supported by processes such as observation, experimentation, ...

description. Some part of the electronic density is delocalised over the whole backbone and the extent of the delocalisation is affected by backbone conformation due to hyper-conjugation effects. Hyper-conjugation arises from donor-acceptor interactions of localised orbitals in 1,3 positions.

Phosphodiesters in DNA and RNA

The phosphodiester backbone of DNA and RNA consists of pairs of

deoxyribose 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. D ...

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 comp ...

sugars linked by phosphates at the respective 3' and 5' positions. The backbone is negatively charged and

hydrophilic A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are n ...

, which allows strong interactions with water. Sugar-phosphate backbone forms the structural framework of

nucleic acids Nucleic acids are large biomolecules that are crucial in all cells and viruses. They are composed of nucleotides, which are the monomer components: a 5-carbon sugar, a phosphate group and a nitrogenous base. The two main classes of nucleic a ...

, including

and

. Sugar phosphates are defined as carbohydrates to which a phosphate group is bound by an ester or an either linkage, depending on whether it involves an alcoholic or a hemiacetalic hydroxyl, respectively.

Solubility In chemistry, solubility is the ability of a chemical substance, substance, the solute, to form a solution (chemistry), solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form su ...

, acid

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

rates, acid strengths, and ability to act as sugar group donors are the knowledge of physical and chemical properties required for the analysis of both types of sugar phosphates. The

photosynthetic Photosynthesis ( ) is a Biological system, system of biological processes by which Photoautotrophism, photosynthetic organisms, such as most plants, algae, and cyanobacteria, convert light energy, typically from sunlight, into the chemical ener ...

carbon reduction cycle is closely associated with sugar phosphates, and sugar phosphates are one of the key molecules in metabolism,(Sugar phosphates are major players in

metabolism Metabolism (, from ''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 cellular processes; the co ...

due to their task of storing and transferring energy. Not only ribose 5-phosphate but also fructose 6-phosphate are an intermediate of the pentose-phosphate pathway which generates

nicotinamide adenine dinucleotide phosphate Nicotinamide adenine dinucleotide phosphate, abbreviated NADP or, in older notation, TPN (triphosphopyridine nucleotide), is a Cofactor (biochemistry), cofactor used in anabolic reactions, such as the Calvin cycle and lipid and nucleic acid synt ...

(NADPH) and pentoses from glucose polymers and their degradation products.) oxidative pentose phosphate pathways,

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 ...

, important intermediates in

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 ...

. Sugar phosphates are not only involved in metabolic regulation and signaling but also involved in the synthesis of other phosphate compounds.

Peptide nucleic acids

Peptide nucleic acid (PNA) is a nucleic acid in which natural nucleic acid has been replaced by a

synthetic peptide In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl ...

backbone formed from ''N''-(2-amino-ethyl)-glycine units along with sugar phosphate backbone forming in an

achiral Chirality () is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is distinguishable from ...

and uncharged moiety that mimics RNA or DNA

oligonucleotide Oligonucleotides are short DNA or RNA molecules, oligomers, that have a wide range of applications in genetic testing, Recombinant DNA, research, and Forensic DNA, forensics. Commonly made in the laboratory by Oligonucleotide synthesis, solid-phase ...

s. PNA cannot be degraded inside living cells but it is chemically stable and resistant to

hydrolytic Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis ...

(enzymatic)

cleavage Cleavage may refer to: Science * Cleavage (crystal), the way in which a crystal or mineral tends to split * Cleavage (embryo), the division of cells in an early embryo * Cleavage (geology), foliation of rock perpendicular to stress, a result of ...

Role in metabolism

Sugar phosphates are major players in

due to their task of storing and transferring energy. Not only ribose 5-phosphate but also fructose 6-phosphate are an intermediate of the pentose-phosphate pathway which generates

(NADPH) and pentoses from glucose polymers and their degradation products. The pathway is known as

where the same carbohydrates are degraded into pyruvates thus providing energy. Enzymes are catalysed for the reactions of these pathways. Some

enzymes An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as pro ...

contain metal centers in their

active site In biology and biochemistry, the active site is the region of an enzyme where substrate molecules bind and undergo a chemical reaction. The active site consists of amino acid residues that form temporary bonds with the substrate, the ''binding s ...

which is important part of the enzymes and as well as for the catalysed reaction. The phosphate group can coordinate to the metal center for example, 1,6-bisphosphatase and ADP-ribose pyrophosphatase. Phosphoglycerate and several sugar phosphates that are known intermediates of the Calvin photosynthetic

carbon cycle The carbon cycle is a part of the biogeochemical cycle where carbon is exchanged among the biosphere, pedosphere, geosphere, hydrosphere, and atmosphere of Earth. Other major biogeochemical cycles include the nitrogen cycle and the water cycl ...

, stimulate light-dependent carbon dioxide fixation by isolated chloroplasts. This ability is shared by certain other metabolites (e.g. glucose 1-phosphate) from which the accepted Calvin-cycle intermediates could easily be derived by known metabolic routes.

References

External links

* {{MeshName, Sugar+Phosphates Glycomics Phosphates Nucleotides DNA RNA