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Encyclopedia > Adenosine monophosphate
Adenosine monophosphate
Chemical name 5'-Adenylic acid
Chemical formula C10H14N5O7P
Molecular mass 347.22 g/mol
CAS number 61-19-8
SMILES O[C@H]1[C@H]([C@@H]
(O[C@@H]1COP(O)(O)=O)
N2C3=C(N=C2)C(N)=NC=N3)O
Chemical structure of deprotonated AMP

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. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass (abbreviated MM) of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Download high resolution version (2510x2067, 14 KB) Wikipedia does not have an article with this exact name. ... A nucleotide is a chemical compound that consists of a heterocyclic base, a sugar, and one or more phosphate groups. ... Ribonucleic acid (RNA) is a nucleic acid polymer consisting of covalently bound nucleotides. ... General formula of an ester of a carboxylic acid. ... R-phrases S-phrases , , Supplementary data page Structure and properties n, εr, etc. ... Nucleosides are glycosylamines made by attaching a nucleobase to a ribose ring. ... The chemical structure of adenosine Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a β-N9-glycosidic bond. ... In chemistry, a phosphate is a polyatomic ion or radical consisting of one phosphorus atom and four oxygen. ... ... A pentose is a monosaccharide with five carbon atoms. ... Magnified view of refined sugar crystals. ... Ribose Ribose is a five carbon sugar (pentose) that is critical to living creatures. ... Adenine Guanine Thymine Cytosine ... Adenine is one of the two purine nucleobases used in forming nucleotides of the nucleic acids DNA and RNA. In DNA, adenine (A) binds to thymine (T) via two hydrogen bonds to assist in stabilizing the nucleic acid structures. ...

Contents


Production and degradation

AMP can be produced during ATP synthesis by the enzyme adenylate kinase by combining two ADP molecules: Adenosine 5-tripenis (ATP) is the nucleotide known in biochemistry as the molecular currency of intracellular energy transfer; that is, ATP is able to store and transport chemical energy within cells. ... Adenylate kinase (also known as ADK) is a phosphotransferase enzyme (EC 2. ... Adenosine diphosphate, abbreviated ADP, is a nucleotide. ...

2 ADP → ATP + AMP

Or AMP may be produced by the hydrolysis of one high energy phosphate bond of ADP: Hydrolysis is a chemical process in which a molecule is split into two parts by the addition of a molecule of water. ... High energy phosphate can mean one of a couple things: It can mean the phosphate-phosphate bonds formed when compounds such as adenosine diphosphate and adenosine triphosphate are created. ...

ADP → AMP + Pi

AMP can also be formed by hydrolysis of ATP into AMP and pyrophosphate: In chemistry, a phosphate is a polyatomic ion or radical consisting of one phosphorus atom and four oxygen. ... Adenosine 5-tripenis (ATP) is the nucleotide known in biochemistry as the molecular currency of intracellular energy transfer; that is, ATP is able to store and transport chemical energy within cells. ... In chemistry, pyrophosphate, or PPi is an anion observed in living systems, usually formed by the hydrolysis of ATP into AMP. The hydrolysis is called pyrophosphorolysis. ...

ATP → AMP + PPi

When RNA is broken down by living systems, nucleoside monophosphates, including adenosine monophosphate, are formed. In chemistry, pyrophosphate, or PPi is an anion observed in living systems, usually formed by the hydrolysis of ATP into AMP. The hydrolysis is called pyrophosphorolysis. ... Ribonucleic acid (RNA) is a nucleic acid polymer consisting of covalently bound nucleotides. ... Nucleosides are glycosylamines made by attaching a nucleobase to a ribose ring. ...


AMP can be regenerated to ATP as follows:

AMP + ATP → 2 ADP (adenylate kinase in the opposite direction)
2 ADP + 2 Pi → 2 ATP (this step is most often performed in aerobes by the ATP synthase during oxidative phosphorylation)

AMP can be converted into IMP by the enzyme myoadenylate deaminase, freeing an ammonia group. An ATP synthase (EC 3. ... Oxidative phosphorylation is a biochemical process in cells. ... Ribbon diagram of the catalytically perfect enzyme TIM. An enzyme is a protein that catalyzes, or speeds up, a chemical reaction. ... Ammonia is a compound of nitrogen and hydrogen with the formula NH3. ...


In a catabolic pathway, adenosine monophosphate can be converted to uric acid, which is excreted from the body. Uric acid is an organic compound of carbon, nitrogen, oxygen and hydrogen and the structure shown right: Uric acid is the final oxidation product of purine metabolism in the human body and is found in small amounts in urine. ...


cAMP

AMP can also exist as a cyclic structure known as cyclic AMP (or cAMP). Within certain cells the enzyme adenylate cyclase makes cAMP from ATP, and typically this reaction is regulated by hormones such as adrenaline or glucagon. cAMP plays an important role in intracellular signalling. Structure of cAMP Cyclic adenosine monophosphate (cAMP, cyclic AMP or 3-5-cyclic adenosine monophosphate) is a molecule that is important in many biological processes; it is derived from adenosine triphosphate (ATP). ... Adenylate cyclase (EC 4. ... Epinephrine (INN) or adrenaline (BAN) is a hormone and a neurotransmitter. ... Glucagon ball and stick model Glucagon is a 29 amino acid polypeptide acting as an important hormone in carbohydrate metabolism. ...


Commercial applications

Linguagen Corp, which is located in Cranbury, New Jersey, obtained FDA approval in September 2004 to employ AMP as a patented 'Bitter Blocker' additive to foodstuffs. To human tastes, the bitterness suppressing quality of AMP interprets as food seeming 'sweeter'. This makes lower calorie food products more palatable, making AMP potentially a lucrative solution for food manufacturers as they respond to pressure from consumers and regulators concerned about social trends towards obesity. The United States Food and Drug Administration is the government agency responsible for regulating food, dietary supplements, drugs, cosmetics, medical devices, biologics and blood products in the United States. ... Look up September in Wiktionary, the free dictionary. ... 2004 (MMIV) was a leap year starting on Thursday of the Gregorian calendar. ...


See also

Nucleosides are glycosylamines made by attaching a nucleobase to a ribose ring. ... A nucleotide is a chemical compound that consists of a heterocyclic base, a sugar, and one or more phosphate groups. ... 3D model of a section of the DNA molecule Deoxyribonucleic acid (DNA) is a nucleic acid that contains the genetic instructions specifying the biological development of all cellular forms of life (and most viruses). ... Ribonucleic acid (RNA) is a nucleic acid polymer consisting of covalently bound nucleotides. ... Oligonucleotides are short sequences of nucleotides (RNA or DNA), typically with twenty or fewer base pairs. ...

External link

  • Computational Chemistry Wiki
Nucleic acids edit
Nucleobases: Adenine - Thymine - Uracil - Guanine - Cytosine - Purine - Pyrimidine
Nucleosides: Adenosine - Uridine - Guanosine - Cytidine - Deoxyadenosine - Thymidine - Deoxyguanosine - Deoxycytidine
Nucleotides: AMP - UMP - GMP - CMP - ADP - UDP - GDP - CDP - ATP - UTP - GTP - CTP - cAMP - cGMP
Deoxynucleotides: dAMP - dTMP - dUMP - dGMP - dCMP - dADP - dTDP - dUDP - dGDP - dCDP - dATP - dTTP - dUTP - dGTP - dCTP
Nucleic acids: DNA - RNA - LNA - PNA - mRNA - ncRNA - miRNA - rRNA - siRNA - tRNA - snRNA - snoRNA - mtDNA - Oligonucleotide

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