Names | |
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IUPAC name 2′-Deoxyadenylic acid | |
Systematic IUPAC name [(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.010.459 |
MeSH | Deoxyadenosine+monophosphate |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C10H14N5O6P | |
Molar mass | 331.222 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Deoxyadenosine monophosphate (dAMP), also known as deoxyadenylic acid or deoxyadenylate in its conjugate acid and conjugate base forms, respectively, is a derivative of the common nucleotide AMP, or adenosine monophosphate, in which the -OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been reduced to just a hydrogen atom (hence the "deoxy-" part of the name). Deoxyadenosine monophosphate is abbreviated dAMP. It is a monomer used in DNA.
Nucleotides are organic molecules composed of a nitrogenous base, a pentose sugar and a phosphate. They serve as monomeric units of the nucleic acid polymers – deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), both of which are essential biomolecules within all life-forms on Earth. Nucleotides are obtained in the diet and are also synthesized from common nutrients by the liver.
Adenine is a purine nucleotide base. It is one of the four nucleobases in the nucleic acids of DNA, the other three being guanine (G), cytosine (C), and thymine (T). Adenine derivatives have various roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD), flavin adenine dinucleotide (FAD) and Coenzyme A. It also has functions in protein synthesis and as a chemical component of DNA and RNA. The shape of adenine is complementary to either thymine in DNA or uracil in RNA.
Thymidine, also known as deoxythymidine, deoxyribosylthymine, or thymine deoxyriboside, is a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in G1/early S phase. The prefix deoxy- is often left out since there are no precursors of thymine nucleotides involved in RNA synthesis.
Adenosine monophosphate (AMP), also known as 5'-adenylic acid, is a nucleotide. AMP consists of a phosphate group, the sugar ribose, and the nucleobase adenine. It is an ester of phosphoric acid and the nucleoside adenosine. As a substituent it takes the form of the prefix adenylyl-.
In biochemistry, a ribonucleotide is a nucleotide containing ribose as its pentose component. It is considered a molecular precursor of nucleic acids. Nucleotides are the basic building blocks of DNA and RNA. Ribonucleotides themselves are basic monomeric building blocks for RNA. Deoxyribonucleotides, formed by reducing ribonucleotides with the enzyme ribonucleotide reductase (RNR), are essential building blocks for DNA. There are several differences between DNA deoxyribonucleotides and RNA ribonucleotides. Successive nucleotides are linked together via phosphodiester bonds.
Thymidine monophosphate (TMP), also known as thymidylic acid, deoxythymidine monophosphate (dTMP), or deoxythymidylic acid, is a nucleotide that is used as a monomer in DNA. It is an ester of phosphoric acid with the nucleoside thymidine. dTMP consists of a phosphate group, the pentose sugar deoxyribose, and the nucleobase thymine. Unlike the other deoxyribonucleotides, thymidine monophosphate often does not contain the "deoxy" prefix in its name; nevertheless, its symbol often includes a "d" ("dTMP"). Dorland’s Illustrated Medical Dictionary provides an explanation of the nomenclature variation at its entry for thymidine.
Uridine monophosphate (UMP), also known as 5′-uridylic acid, is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside uridine. UMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase uracil; hence, it is a ribonucleotide monophosphate. As a substituent or radical its name takes the form of the prefix uridylyl-. The deoxy form is abbreviated dUMP. Covalent attachment of UMP is called uridylylation.
Inosinic acid or inosine monophosphate (IMP) is a nucleotide. Widely used as a flavor enhancer, it is typically obtained from chicken byproducts or other meat industry waste. Inosinic acid is important in metabolism. It is the ribonucleotide of hypoxanthine and the first nucleotide formed during the synthesis of purine nucleotides. It can also be formed by the deamination of adenosine monophosphate by AMP deaminase. It can be hydrolysed to inosine.
Nucleic acid metabolism is a collective term that refers to the variety of chemical reactions by which nucleic acids are either synthesized or degraded. Nucleic acids are polymers made up of a variety of monomers called nucleotides. Nucleotide synthesis is an anabolic mechanism generally involving the chemical reaction of phosphate, pentose sugar, and a nitrogenous base. Degradation of nucleic acids is a catabolic reaction and the resulting parts of the nucleotides or nucleobases can be salvaged to recreate new nucleotides. Both synthesis and degradation reactions require multiple enzymes to facilitate the event. Defects or deficiencies in these enzymes can lead to a variety of diseases.
Deoxyguanosine monophosphate (dGMP), also known as deoxyguanylic acid or deoxyguanylate in its conjugate acid and conjugate base forms, respectively, is a derivative of the common nucleotide guanosine triphosphate (GTP), in which the –OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been reduced to just a hydrogen atom. It is used as a monomer in DNA.
Deoxyadenosine diphosphate is a nucleoside diphosphate. It is related to the common nucleic acid ATP, or adenosine triphosphate, with the -OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose removed, and with one fewer phosphoryl group than ATP. This makes it also similar to adenosine diphosphate except with a hydroxyl group removed.
Deoxycytidine monophosphate (dCMP), also known as deoxycytidylic acid or deoxycytidylate in its conjugate acid and conjugate base forms, respectively, 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.
Purine metabolism refers to the metabolic pathways to synthesize and break down purines that are present in many organisms.
Guanosine monophosphate synthetase, also known as GMPS is an enzyme that converts xanthosine monophosphate to guanosine monophosphate.
GMP reductase EC 1.7.1.7 is an enzyme that catalyzes the irreversible and NADPH-dependent reductive deamination of GMP into IMP.
Deoxyuridine monophosphate (dUMP), also known as deoxyuridylic acid or deoxyuridylate in its conjugate acid and conjugate base forms, respectively, is a deoxynucleotide.
Nucleotidyltransferases are transferase enzymes of phosphorus-containing groups, e.g., substituents of nucleotidylic acids or simply nucleoside monophosphates. The general reaction of transferring a nucleoside monophosphate moiety from A to B, can be written as:
In enzymology, an adenosine-phosphate deaminase (EC 3.5.4.17) is an enzyme that catalyzes the chemical reaction
Deoxyinosine monophosphate (dIMP) is a nucleoside monophosphate and a derivative of inosinic acid. It can be formed by the deamination of the purine base in deoxyadenosine monophosphate (dAMP). The enzyme deoxyribonucleoside triphosphate pyrophosphohydrolase, encoded by YJR069C in S. cerevisiae and containing (d)ITPase and (d)XTPase activities, hydrolyses dITP, resulting in the release of pyrophosphate and dIMP.