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Encyclopedia > Nucleotide

A nucleotide is a chemical compound that consists of 3 portions: a heterocyclic base, a sugar, and one or more phosphate groups. In the most common nucleotides the base is a derivative of purine or pyrimidine, and the sugar is the pentose (five-carbon sugar) deoxyribose or ribose. Nucleotides are the monomers of nucleic acids, with three or more bonding together in order to form a nucleic acid. Look up chemical compound in Wiktionary, the free dictionary. ... Basic aromatic rings are aromatic rings in which the lone pair of electrons of a ring_nitrogen atom is not part of the aromatic system and extends in the plane of the ring. ... This article is about sugar as food and as an important and widely traded commodity. ... A phosphate, in inorganic chemistry, is a salt of phosphoric acid. ... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... Purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. ... Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring [1]. It is isomeric with two other forms of diazine. ... A pentose is a monosaccharide with five carbon atoms. ... Deoxyribose Deoxyribose, also known as D-Deoxyribose and 2-deoxyribose, is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde functional group. ... Ribose Ribose, primarily seen as D-ribose, is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde functional group. ... In chemistry, a monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer. ... Highly simplified diagram of a double-stranded nucleic acid. ...


Nucleotides are the structural units of RNA, DNA, and several cofactors - CoA, flavin adenine dinucleotide, flavin mononucleotide, adenosine triphosphate and nicotinamide adenine dinucleotide phosphate. In the cell they have important roles in metabolism and signaling. Left: An RNA strand, with its nitrogenous bases. ... The structure of part of a DNA double helix Deoxyribonucleic acid, or DNA, is a nucleic acid molecule that contains the genetic instructions used in the development and functioning of all known living organisms. ... Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. ... For other uses, see FAD (disambiguation). ... Flavin mononucleotide or FMN is derived from riboflavin (vitamin B2) and functions as cofactor of various oxidoreductases. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... Nicotinamide adenine dinucleotide phosphate (NADP) is used in anabolic reactions, such as fatty acid and nucleic acid synthesis, which require NADPH as a reducing agent. ... Drawing of the structure of cork as it appeared under the microscope to Robert Hooke from Micrographia which is the origin of the word cell being used to describe the smallest unit of a living organism Cells in culture, stained for keratin (red) and DNA (green) The cell is the... Structure of the coenzyme adenosine triphosphate, a central intermediate in energy metabolism. ...

The structure elements of the most common nucleotides
The structure elements of the most common nucleotides

Contents

Image File history File links No higher resolution available. ...

Nucleotides

Chemical structure of adenosine monophosphate
Adenosine monophosphate
AMP
Chemical structure of adenosine diphosphate
Adenosine diphosphate
ADP
Chemical structure of adenosine triphosphate
Adenosine triphosphate
ATP
Chemical structure of guanosine monophosphate
Guanosine monophosphate
GMP
Chemical structure of guanosine diphosphate
Guanosine diphosphate
GDP
Chemical structure of guanosine triphosphate
Guanosine triphosphate
GTP
Chemical structure of ribothymidine monophosphate
Ribothymidine monophosphate
rTMP
Chemical structure of ribothymidine diphosphate
Ribothymidine diphosphate
rTDP
Chemical structure of ribothymidine triphosphate
Ribothymidine triphosphate
rTTP
Chemical structure of uridine monophosphate
Uridine monophosphate
UMP
Chemical structure of uridine diphosphate
Uridine diphosphate
UDP
Chemical structure of uridine triphosphate
Uridine triphosphate
UTP
Chemical structure of cytidine monophosphate
Cytidine monophosphate
CMP
Chemical structure of cytidine diphosphate
Cytidine diphosphate
CDP
Chemical structure of cytidine triphosphate
Cytidine triphosphate
CTP

Image File history File links AMP_structure. ... Adenosine monophosphate, also known as 5-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. ... Image File history File links ADP_structure. ... Adenosine diphosphate, abbreviated ADP, is a nucleotide. ... Image File history File links ATP_structure. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... Download high resolution version (3074x2071, 16 KB) Wikipedia does not have an article with this exact name. ... Guanosine monophosphate, also known as 5-guanidylic acid and abbreviated GMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside guanosine. ... Download high resolution version (3678x2071, 18 KB) Wikipedia does not have an article with this exact name. ... Guanosine diphosphate, abbreviated GDP, is a nucleotide. ... Download high resolution version (4282x2071, 20 KB) Wikipedia does not have an article with this exact name. ... Guanosine triphosphate (GTP) is also known as guanosine-5-triphosphate. ... Download high resolution version (2346x1995, 12 KB) Wikipedia does not have an article with this exact name. ... Download high resolution version (2954x1995, 15 KB) Wikipedia does not have an article with this exact name. ... Download high resolution version (3558x1995, 17 KB) Wikipedia does not have an article with this exact name. ... Download high resolution version (2346x1999, 12 KB) Wikipedia does not have an article with this exact name. ... Uridine monophosphate, also known as 5-uridylic acid and abbreviated UMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside uridine. ... Download high resolution version (2954x1999, 14 KB) Wikipedia does not have an article with this exact name. ... Uridine diphosphate, abbreviated UDP, is a nucleotide. ... Download high resolution version (3558x1999, 16 KB) Wikipedia does not have an article with this exact name. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide primarily known in biochemistry as the molecular currency of intracellular energy transfer. ... Download high resolution version (2346x1994, 12 KB) Wikipedia does not have an article with this exact name. ... Cytidine monophosphate, also known as 5-cytidylic acid and abbreviated CMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside cytidine. ... Download high resolution version (2950x1994, 15 KB) Wikipedia does not have an article with this exact name. ... Cytidine diphosphate, abbreviated CDP, is a nucleotide. ... Download high resolution version (3558x1994, 16 KB) Wikipedia does not have an article with this exact name. ... Cytidine triphosphate is a pyrimidine nucleotide. ...

Deoxynucleotides

Chemical structure of deoxyadenosine monophosphate
Deoxyadenosine monophosphate
dAMP
Chemical structure of deoxyadenosine diphosphate
Deoxyadenosine diphosphate
dADP
Chemical structure of deoxyadenosine triphosphate
Deoxyadenosine triphosphate
dATP
Chemical structure of deoxyguanosine monophosphate
Deoxyguanosine monophosphate
dGMP
Chemical structure of deoxyguanosine diphosphate
Deoxyguanosine diphosphate
dGDP
Chemical structure of deoxyguanosine triphosphate
Deoxyguanosine triphosphate
dGTP
Chemical structure of thymidine monophosphate
Thymidine monophosphate
TMP
Chemical structure of thymidine diphosphate
Thymidine diphosphate
TDP
Chemical structure of thymidine triphosphate
Thymidine triphosphate
TTP
Chemical structure of deoxyuridine monophosphate
Deoxyuridine monophosphate
dUMP
Chemical structure of deoxyuridine diphosphate
Deoxyuridine diphosphate
dUDP
Chemical structure of deoxyuridine triphosphate
Deoxyuridine triphosphate
dUTP
Chemical structure of deoxycytidine monophosphate
Deoxycytidine monophosphate
dCMP
Chemical structure of deoxycytidine diphosphate
Deoxycytidine diphosphate
dCDP
Chemical structure of deoxycytidine triphosphate
Deoxycytidine triphosphate
dCTP

NOTE: If in place of ribose , the sugar deoxyribose is present the prefix `deoxy` may be added before the name of the nucleoside in all cases except thymidine. Download high resolution version (2510x2067, 14 KB) Wikipedia does not have an article with this exact name. ... This article belongs in one or more categories. ... Download high resolution version (3118x2067, 16 KB) Wikipedia does not have an article with this exact name. ... Deoxyadenosine diphosphate is a derivative of the common nucleic acid ATP, or adenosine triphosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been removed (hence the deoxy- part of the name). ... Download high resolution version (3722x2067, 18 KB) Wikipedia does not have an article with this exact name. ... Deoxy adenosine triphosphate produces energy within the cells and is the basis for normal functioning of all body systems and organs. ... Download high resolution version (3074x2067, 15 KB) Wikipedia does not have an article with this exact name. ... Deoxyguanosine monophosphate is a derivative of the common nucleic acid GTP, or guanosine triphosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been reduced to just a hydrogen atom (hence the deoxy- part of the name). ... Download high resolution version (3674x2067, 17 KB) Wikipedia does not have an article with this exact name. ... Deoxyguanosine diphosphate is a derivative of the common nucleic acid GTP, or guanosine triphosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been removed (hence the deoxy- part of the name). ... Download high resolution version (4282x2067, 20 KB) Wikipedia does not have an article with this exact name. ... The chemical structure of dGTP Deoxyguanosine triphosphate, normally shortened to dGTP has a chemical structure of Na4 â€¢ 3 H2O and a molecular weight of 649. ... Download high resolution version (2350x1991, 12 KB) Wikipedia does not have an article with this exact name. ... Thymidine monophosphate, also known as 5-thymidylic acid and abbreviated TMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside thymidine. ... Download high resolution version (2954x1991, 15 KB) Wikipedia does not have an article with this exact name. ... Thymidine diphosphate, abbreviated TDP, is a nucleotide. ... Download high resolution version (3558x1991, 16 KB) Wikipedia does not have an article with this exact name. ... 3D-Model of thymidine triphosphate Thymidine triphosphate or TTP is one of the four nucleoside triphosphates that make up DNA. It can be used by DNA ligase to create overlapping sticky ends so that protruding ends of opened microbial plasmids maybe closed up. ... Download high resolution version (2350x1999, 11 KB) Wikipedia does not have an article with this exact name. ... Deoxyuridine monophosphate is a deoxynucleotide. ... Download high resolution version (2954x1999, 14 KB) Wikipedia does not have an article with this exact name. ... Download high resolution version (3558x1999, 16 KB) Wikipedia does not have an article with this exact name. ... Download high resolution version (2350x1995, 12 KB) Wikipedia does not have an article with this exact name. ... Deoxycytidine monophosphate is a deoxynucleotide, and one of the four monomers that make up DNA. In a DNA double helix, it will base pair with deoxyguanosine monophosphate. ... Download high resolution version (2954x1995, 14 KB) Wikipedia does not have an article with this exact name. ... Please wikify (format) this article or section as suggested in the Guide to layout and the Manual of Style. ... Download high resolution version (3558x1995, 16 KB) Wikipedia does not have an article with this exact name. ... This article or section is in need of attention from an expert on the subject. ...


Synthesis

Salvage synthesis refers to the reuse of parts of nucleotides in resynthesizing new nucleotides. Salvage synthesis requires both breakdown and synthesis reactions in order to exchange the useful parts. A nucleotide is an organic molecule consisting of a heterocyclic nucleobase (a purine or a pyrimidine), a pentose sugar (deoxyribose in DNA or ribose in RNA), and a phosphate or polyphosphate group. ...


Natural

Purine ribonucleotides

By using a variety of isotopically labelled compounds it was demonstrated that the sources of the atoms in purines are as follows:

Image:Nucleotides syn3.png The biosynthetic origins of purine ring atoms

N1 arises from the amine group of Asp
C2 and C8 originate from formate
N3 and N9 are contributed by the amide group of Gln
C4, C5 and N7 are derived from Gly
C6 comes from HCO3- (CO2)
The synthesis of IMP.The color scheme is as follows: enzymes, coenzymes, substrate names, metal ions, inorganic molecules
The synthesis of IMP.
The color scheme is as follows: enzymes, coenzymes, substrate names, metal ions, inorganic molecules

The de novo synthesis of purine nucleotides by which these precursors are incorporated into the purine ring, proceeds by a 10 step pathway to the branch point intermediate IMP, the nucleotide of the base hypoxanthine. AMP and GMP are subsequently synthesized from this intermediate via separate, two step each, pathways. Thus purine moieties are initially formed as part of the ribonucleotides rather than as free bases. Image File history File links Nucleotides_syn3. ... Aspartic acid (abbreviated as Asp or D; Asx or B represent either aspartic acid or asparagine[1] ) is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CO2H. The L-isomer is a protonated varient of one of the 20 proteinogenic amino acids, i. ... Formate or methanoate is the ion is HCOO- (formic acid minus one hydrogen ion). ... Glutamine (abbreviated as Gln or Q; Glx or Z represents either glutamine or glutamic acid) is one of the 20 amino acids encoded by the standard genetic code. ... For the plant, see Glycine (plant). ... Image File history File links Download high resolution version (593x607, 37 KB) Summary Licensing I, the creator of this work, hereby release it into the public domain. ... Image File history File links Download high resolution version (593x607, 37 KB) Summary Licensing I, the creator of this work, hereby release it into the public domain. ... In general usage, de novo is a Latin expression meaning afresh, anew, beginning again. In USA Banking, a de novo bank is defined as a state member bank that has been in operation for five years or less. ... Hypoxanthine is a naturally occurring purine derivative, and one of the products of the action of xanthine oxidase on xanthine, though more normally in purine degradation, hypoxanthine is oxidized by xanthine oxidase to form xanthine. ... Look up moiety in Wiktionary, the free dictionary. ...


Six enzymes take part in IMP synthesis. Three of them are multifunctional:

  • GART (reactions 2, 3, and 5)
  • PAICS (reactions 6, and 7)
  • ATIC (reactions 9, and 10)

Reaction 1. The pathway starts with the formation of PRPP. PRPS1 is the enzyme that activates R5P, which is primarily formed by the pentose phosphate pathway, to PRPP by reacting it with ATP. The reaction is unusual in that a pyrophosphoryl group is directly transferred from ATP to C1 of R5P and that the product has the α configuration about C1. This reaction is also shared with the pathways for the synthesis of the pyrimidine nucleotides, Trp, and His. As a result of being on (a) such (a) major metabolic crossroad and the use of energy, this reaction is highly regulated. Phosphoribosylglycinamide formyltransferase is an enzyme involved in the synthesis of purines. ... Phosphoribosylaminoimidazole carboxylase is an enzyme involved in nucleotide synthesis. ... Inosine monophosphate synthase is an enzyme which generates inosine monophosphate from aminoimidazole carboxamide ribonucleotide. ... Phosphoribosyl pyrophosphate (PRPP) is a pentosephosphate. ... Ribose-phosphate diphosphokinase (or phosphoribosyl pyrophosphate synthetase) is an enzyme which converts ribose 5-phosphate into phosphoribosyl pyrophosphate. ... Ribose 5-phosphate is both a product and an intermediate of the pentose phosphate pathway. ... The pentose phosphate pathways Nonoxidative phase The pentose phosphate pathway (also called Phosphogluconate Pathway, or Hexose Monophosphate Shunt [HMP shunt]) is a process that serves to generate NADPH and the synthesis of pentose (5-carbon) sugars. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... Tryptophan (abbreviated as Trp or W)[1] is one of the 20 standard amino acids, which are the building blocks of proteins, and an essential amino acid in the human diet. ... Histidine is one of the 20 most common natural amino acids present in proteins. ...


Reaction 2. In the first reaction unique to purine nucleotide biosynthesis, PPAT catalyzes the displacement of PRPP's pyrophosphate group (PPi) by Gln's amide nitrogen. The reaction occurs with the inversion of configuration about ribose C1, thereby forming β-5-phosphorybosylamine (5-PRA) and establishing the anomeric form of the future nucleotide. This reaction which is driven to completion by the subsequent hydrolysis of the released PPi, is the pathway's flux generating step and is therefore regulated too. Amidophosphoribosyltransferase (or phosphoribosyl pyrophosphate amidotransferase) is an enzyme which converts phosphoribosylpyrophosphate (PRPP) into 5-phosphoribosylamine. ... Phosphoribosylamine (5PRA) is an intermediate in purine metabolism. ...


Reaction 3.


Pyrimidine ribonucleotides

The synthesis of UMP.The color scheme is as follows: enzymes, coenzymes, substrate names, inorganic molecules
The synthesis of UMP.
The color scheme is as follows: enzymes, coenzymes, substrate names, inorganic molecules

Image File history File links Nucleotides_syn2. ... Image File history File links Nucleotides_syn2. ...

Protection Chemistry

Nucleic acids can be synthesised in the lab. using protecting groups, typically this is achieved by protecting a purified nucleoside or nucleobase, a protected base is called a phosphoramidite. these can be used to obtain analogues not present in nature and/or to create an oligonucleotide. A Protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction. ... Nucleoside phosphoramidites are used to synthesise short nucleic acid chains. ... Oligonucleotide synthesis is the non-biological, chemical synthesis of defined short sequences of nucleic acids. ...


References

See also

For other uses, see Gene (disambiguation). ... This article is about the general scientific term. ... A scheme of a condensed (metaphase) chromosome. ... Adenine Guanine Thymine Cytosine ... Nucleic acid analogues are compounds structurally similar to naturally occuring RNA and DNA, used as a research tool in molecular biology and/or as cure in medicine. ...

External links


The International Union of Pure and Applied Chemistry (IUPAC) is an international non-governmental organization devoted to the advancement of chemistry. ...

v  d  e
Major families of biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids: Types of Nucleic Acids Analogues of nucleic acids:
Nucleobases: Purine (Adenine, Guanine) | Pyrimidine (Uracil, Thymine, Cytosine)
Nucleosides: Adenosine/Deoxyadenosine | Guanosine/Deoxyguanosine | Uridine | Thymidine | Cytidine/Deoxycytidine
Nucleotides: monophosphates (AMP, UMP, GMP, CMP) | diphosphates (ADP, UDP, GDP, CDP) | triphosphates (ATP, UTP, GTP, CTP) | cyclic (cAMP, cGMP, cADPR)
Deoxynucleotides: monophosphates (dAMP, TMP, dGMP, dCMP) | diphosphates (dADP, TDP, dGDP, dCDP) | triphosphates (dATP, TTP, dGTP, dCTP)
Ribonucleic acids: RNA | mRNA | piRNA | tRNA | rRNA | ncRNA | gRNA | shRNA | siRNA | snRNA | miRNA | snoRNA
Deoxyribonucleic acids: DNA | mtDNA | cDNA | plasmid | Cosmid | BAC | YAC | HAC
Analogues of nucleic acids: GNA | PNA | TNA | Morpholino | LNA

  Results from FactBites:
 
Nucleotide - Wikipedia, the free encyclopedia (551 words)
A nucleotide is a chemical compound that consists of a heterocyclic base, a sugar, and one or more phosphate groups.
In the most common nucleotides the base is a derivative of purine or pyrimidine, and the sugar is the pentose (five-carbon sugar) deoxyribose or ribose.
Nucleotides are the structural units of RNA, DNA, and several cofactors - CoA, FAD, FMN, NAD, and NADP.
Nucleotide (337 words)
A nucleotide is the monomer structural unit of nucleotide chains that form the nucleic acids RNA and DNA, as well as several lesser nucleic acids.
Nucleotides code for proteins and enzymes as well as determine the genetic structure of life.
Nucleotides are also crucial for cellular energy transportation and transformation and in the regulation of enzymes.
  More results at FactBites »

 
 

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