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Serine (abbreviated as Ser or S) is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
O
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
2C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
CH(N
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
H2)CH2OH.

s one of the 20 naturally occurring proteinogenic amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
s. Its codons are UCU, UCC, UCA, UCG, AGU and AGC. Only the L-stereoisomer appears naturally in proteins. It is not essential to the human diet, since it is synthesized in the body from other metabolites, including glycine
Glycine

Glycine is the organic compound with the chemical formula NH2CH2COOH. It is the smallest of the 20 amino acids commonly found in proteins, coded by codons GGU, GGC, GGA and GGG....
.






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Serine (abbreviated as Ser or S) is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
O
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
2C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
CH(N
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
H2)CH2OH.

Occurrence

It is one of the 20 naturally occurring proteinogenic amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
s. Its codons are UCU, UCC, UCA, UCG, AGU and AGC. Only the L-stereoisomer appears naturally in proteins. It is not essential to the human diet, since it is synthesized in the body from other metabolites, including glycine
Glycine

Glycine is the organic compound with the chemical formula NH2CH2COOH. It is the smallest of the 20 amino acids commonly found in proteins, coded by codons GGU, GGC, GGA and GGG....
. Serine was first obtained from silk
Silk

Silk is a natural protein fiber, some forms of which can be weaving into textiles. The best-known type of silk is obtained from Pupa#Cocoons made by the larvae of the mulberry silkworm Bombyx mori reared in captivity ....
 protein, a particularly rich source, in 1865. Its name is derived from the Latin
Latin

Latin is an Italic language, historically spoken in Latium and Ancient Rome. Through the Military history of the Roman Empire, Latin spread throughout the Mediterranean and a large part of Europe....
 for silk, sericum. Serine's structure was established in 1902. By virtue of the hydroxyl group, serine is classified as a polar amino acid.

Biosynthesis


The biosynthesis of serine starts with the oxidation of 3-phosphoglycerate to 3-phosphohydroxypyruvate and NADH. Reductive amination
Reductive amination

Reductive amination is a chemical reaction which involves the conversion of a carbonyl group to an amine, via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde....
 of this ketone followed by hydrolysis gives serine. Serine hydroxymethyltransferase
Serine hydroxymethyltransferase

Serine hydroxymethyltransferase is an enzyme which plays an important role in cellular one-carbon pathways by catalyzing the reversible, simultaneous conversions of L-serine to glycine and 5,6,7,8-tetrahydrofolate to 5,10-methylenetetrahydrofolate ....
 catalyzes the reversible, simultaneous conversions of L-serine to glycine
Glycine

Glycine is the organic compound with the chemical formula NH2CH2COOH. It is the smallest of the 20 amino acids commonly found in proteins, coded by codons GGU, GGC, GGA and GGG....
 (retro-aldol cleavage) and 5,6,7,8-tetrahydrofolate to 5,10-methylenetetrahydrofolate
5,10-Methylenetetrahydrofolate

5,10-Methylenetetrahydrofolate is the substrate used by methylenetetrahydrofolate reductase to generate 5-methyltetrahydrofolate. This is a coenzyme used in thymidine biosynthesis by thymidylate synthase ....
 (hydrolysis).

Chemical synthesis

Racemic serine can be prepared from methyl acrylate
Methyl acrylate

Methyl acrylate is a volatile alpha beta unsubstituted methyl ester used in the preparation of polyamidoamine dendrimers typically by Michael addition with a primary amine....
 via several steps. It is also naturally produced when UV light illuminates simple ices such as a combination of water, methanol, hydrogen cyanide, and ammonia, suggesting that it may be easily produced in cold regions of space.

Function


Metabolic


Serine is important in metabolism
Metabolism

Metabolism is the set of chemical reactions that occur in living organisms in order to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments....
 in that it participates in the biosynthesis
Biosynthesis

Biosynthesis is a phenomenon wherein chemical compounds are produced from simpler reagents. Biosynthesis, unlike chemosynthesis, takes place within living organisms and is generally catalyst by enzymes....
 of purines and pyrimidines. It is also the precursor to several amino acids, including glycine
Glycine

Glycine is the organic compound with the chemical formula NH2CH2COOH. It is the smallest of the 20 amino acids commonly found in proteins, coded by codons GGU, GGC, GGA and GGG....
, cysteine
Cysteine

Cysteine is an a-amino acid with the chemical formula HO2CCHCH2SH. It is a non-essential amino acid, which means that humans can synthesize it....
, and, in bacteria, tryptophan
Tryptophan

Tryptophan is one of the 20 List of standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG....
. It is also the precursor to numerous of other metabolites, including sphingolipid
Sphingolipid

Sphingolipids are a class of lipids derived from the aliphatic amino alcohol sphingosine. These compounds are ubiquitous, playing important roles in signal transmission and cell recognition....
s. Serine is also a precursor to folate, which is the principal donor of one carbon fragments in biosynthesis.

Structural role

Serine plays an important role in the catalytic function of many enzyme
Enzyme

Enzymes are biomolecules that catalysis chemical reactions. Almost all enzymes are proteins. In enzymatic reactions, the molecules at the beginning of the process are called Substrate , and the enzyme converts them into different molecules, the products....
s. It has been shown to occur in the active sites of chymotrypsin
Chymotrypsin

Chymotrypsin is a digestive enzyme that can perform proteolysis. Chymotrypsin cleaves peptides at the carboxyl side of tyrosine, tryptophan, and phenylalanine because these three amino acids contain aromatic rings, which fit into a 'hydrophobic pocket' in the enzyme....
, trypsin
Trypsin

Trypsin is a serine protease found in the digestive system, where it breaks down proteins. Trypsin predominantly cleaves peptide chains at the carboxyl side of the amino acids lysine and arginine, except when either is followed by proline....
, and many other enzymes. The so-called nerve gases and many substances used in insecticide
Insecticide

An insecticide is a pesticide used against insects in all developmental forms. They include ovicides and larvicides used against the Egg and larvae of insects respectively....
s have been shown to act by combining with a residue of serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. The unmetabolized acetylcholine cannot be recycled into the nerve for signaling. This results in depletion of acetylcholine
Acetylcholine

The chemical compound acetylcholine is a neurotransmitter in both the peripheral nervous system and central nervous system in many organisms including homo sapiens....
 at the neuromuscular junction, resulting in the inability to control muscles, which results in asphyxia
Asphyxia

Asphyxia is a condition of severely deficient supply of oxygen to the body that arises from being unable to breathe normally. An example of asphyxia is choking....
tion, and death.

As a constituent (residue) of proteins, its side chain
Side chain

A side chain in organic chemistry and biochemistry is a part of a molecule that is attached to a core structure. The placeholder R is often used as a generic placeholder for side chains, the R historically being derived from radical or rest....
 can undergo O-linked glycosylation
Glycosylation

Glycosylation is the enzymatic process that links saccharides to produce glycans, either free or attached to proteins and lipids. This enzymatic process produces one of four fundamental components of all cells and also provides a co-translational and post-translational modification mechanism that modulates the structure and function of membr...
, which may be functionally related to diabetes. It is one of three amino acid residues that are commonly phosphorylated
Phosphorylation

Phosphorylation is the addition of a phosphate group to a protein or other organic molecule. Protein phosphorylation in particular plays a significant role in a wide range of cellular processes....
 by kinases during cell signaling
Signal transduction

In biology, 'signal transduction' refers to any process by which a cell converts one kind of signal or stimulus into another. Most processes of signal transduction involve ordered sequences of biochemistry chemical reaction inside the cell, which are carried out by enzymes, activated by Second messenger systems, resulting in a signal tran...
 in eukaryote
Eukaryote

Animals, plants, fungus, and protists are eukaryotes , organisms whose Cell are organized into complex structures enclosed within Cell membrane....
s. Phosphorylated serine residues are often referred to as phosphoserine
Phosphoserine

Phosphoserine is an ester of serine and phosphoric acid. Phosphoserine is a component of many proteins as the result of posttranslational modifications....
. Serine protease
Serine protease

Serine proteases or serine endopeptidases are proteases in which one of the amino acids at the active site is serine.They are found in both single-cell and complex organisms, in both cells with nuclei and without nuclei ....
s are a common type of protease.

Signaling

D-serine, synthesized by serine racemase
Serine racemase

Serine racemase is an enzyme which generates D-serine from L-serine. D-serine acts as a neuronal signaling molecule by activating NMDA receptors in the brain....
 from L-serine, serves as a neuronal signal by activating NMDA receptor
NMDA receptor

The NMDA receptor is an ionotropic receptor for glutamate . Activation of NMDA receptors results in the opening of an ion channel that is nonselective to ion....
s in the brain.

See also

  • Serine aggregation properties in Serine octamer cluster
    Serine octamer cluster

    The Serine octamer cluster in physical chemistry is an unusually stable cluster consisting of eight serine molecules implicated in the origin of homochirality....
    s