Chemical structure of L-alanine
Alanine
Systematic (IUPAC) name
(S)-2-aminopropanoic acid
Identifiers
CAS number	56-41-7
PubChem	5950
Chemical data
Formula	C3H7NO2
Molar mass	89. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component 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 Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 1 g/mol
SMILES	C[C@H](N)C(O)=O
Complete data

Alanine (abbreviated as Ala or A)^[1] is an α-amino acid with the chemical formula HO₂CCH(NH₂)CH₃. In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this 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 The L-isomer is one of the 20 proteinogenic amino acids, i. Proteinogenic Amino acids also known as standard normal or primary amino acids are those 20 amino acids that are found in Proteins and that are coded for in the e. the building blocks of proteins. Proteins are large Organic compounds made of Amino acids arranged in a linear chain and joined together by Peptide bonds between the Carboxyl Its codons are GCU, GCC, GCA, and GCG. It is classified as a non-polar amino acid. L-alanine is second only to leucine, accounting for 7. Leucine (abbreviated as Leu or L) is an α- Amino acid with the Chemical formula HO2CCH(NH2CH2CH(CH32 8% of the primary structure in a sample of 1,150 proteins. In Biochemistry, the primary structure of a biological molecule is the exact specification of its atomic composition and the chemical bonds connecting those atoms (including Proteins are large Organic compounds made of Amino acids arranged in a linear chain and joined together by Peptide bonds between the Carboxyl ^[2] D-alanine occurs in bacterial cell walls and in some peptide antibiotics.

Contents 1 Structure 2 Sources 2.1 Dietary Sources 2.2 Biosynthesis 2.3 Chemical Synthesis 3 Physiological function 3.1 As a carrier of ammonia and of the carbon skeleton of pyruvate in alanine cycle 3.2 Link to hypertension 4 Chemical properties 4.1 Free radical stability 5 References 6 See also 7 External links

Structure

The α-carbon atom of alanine is bound with a methyl group (-CH₃), making it one of the simplest α-amino acids with respect to molecular structure and also resulting in alanine being classified as an aliphatic amino acid. The alpha carbon in Organic chemistry refers to the first carbon that attaches to a Functional group (the carbon is attached at the first or alpha position In Chemistry, a methyl group is a Hydrophobic Alkyl Functional group named after Methane (4 In Organic chemistry, compounds composed of Carbon and Hydrogen are divided into two classes Aromatic compounds which contain Benzene rings The methyl group of alanine is non-reactive and is thus almost never directly involved in protein function.

Sources

Dietary Sources

Alanine is a nonessential amino acid, meaning it can be manufactured by the human body, and does not need to be obtained directly through the diet. An essential amino acid or indispensable amino acid is an Amino acid that cannot be synthesized de novo by the organism (usually referring to Alanine is found in a wide variety of foods, but is particularly concentrated in meats.

Good sources of alanine include:

• Animal sources: meat, seafood, caseinate, dairy products, eggs, fish, gelatin, lactalbumin
• Vegetarian sources: beans, nuts, seeds, soy, whey, brewer's yeast, brown rice bran, corn, legumes, whole grains.

Biosynthesis

Alanine can be manufactured in the body from pyruvate and branched chain amino acids such as valine, leucine, and isoleucine. Pyruvic acid (CH3COCO2H is an alpha-keto acid. The Carboxylate Anion of pyruvic acid is known as pyruvate. Valine (abbreviated as Val or V) is an α- Amino acid with the Chemical formula HO2CCH(NH2CH(CH32 Leucine (abbreviated as Leu or L) is an α- Amino acid with the Chemical formula HO2CCH(NH2CH2CH(CH32 Isoleucine (abbreviated as Ile or I) is an α- Amino acid with the Chemical formula HO2CCH(NH2CH(CH3CH2CH3

Alanine is most commonly produced by reductive amination of pyruvate. Reductive amination (also known as Reductive alkylation) is a Chemical reaction which involves the conversion of a Carbonyl group to an Amine Pyruvic acid (CH3COCO2H is an alpha-keto acid. The Carboxylate Anion of pyruvic acid is known as pyruvate. Because transamination reactions are readily reversible and pyruvate pervasive, alanine can be easily formed and thus has close links to metabolic pathways such as glycolysis, gluconeogenesis, and the citric acid cycle. There are two chemical reactions known as transamination (or aminotransfer See also Gluconeogenesis, which carries out a process wherein glucose is synthesized rather than catabolized Gluconeogenesis (abreviated GNG) is a Metabolic pathway that results in the generation of Glucose from non- Carbohydrate carbon substrates such The citric acid cycle, also known as the tricarboxylic acid cycle ( TCA cycle) or the Krebs cycle, (or rarely the Szent-Györgyi–Krebs cycle It also arises together with lactate and generates glucose from protein via the alanine cycle. The alanine cycle is quite similar to the Cori cycle. When muscles produce lactate during times of decreased oxygen they also produce Alanine.

Chemical Synthesis

Racemic alanine can be prepared via the condensation of acetaldehyde with ammonium chloride in the presence of potassium cyanide by the Strecker reaction. In Chemistry, a racemic mixture, or racemate, is one that has equal amounts of left- and right-handed enantiomers of a chiral Acetaldehyde, sometimes known as ethanal, is an organic chemical compound with the formula C[[Hydrogen H]]3CH O or MeCHO Ammonium chloride ( N[[Hydrogen H]]4 Cl) (also Sal Ammoniac, salmiac, nushadir salt, zalmiak, sal armagnac Potassium cyanide is an Inorganic compound with the formula KCN The Strecker amino acid synthesis, devised by Adolph Strecker, is a series of Chemical reactions that synthesize an Amino acid from an Aldehyde ^[3]

Physiological function

As a carrier of ammonia and of the carbon skeleton of pyruvate in alanine cycle

Alanine plays a key role in glucose-alanine cycle between tissues and liver. The alanine cycle is quite similar to the Cori cycle. When muscles produce lactate during times of decreased oxygen they also produce Alanine. In muscle and other tissues that degrade amino acids for fuel, amino groups are collected in the form of glutamate by transamination. There are two chemical reactions known as transamination (or aminotransfer Glutamate can then transfer its amino group through the action of alanine aminotransferase to pyruvate, a product of muscle glycolysis, forming alanine and alpha-ketoglutarate. Alanine transaminase or ALT is a Transaminase Enzyme ( It is also called serum glutamic pyruvic transaminase (SGPT or alanine aminotransferase Pyruvic acid (CH3COCO2H is an alpha-keto acid. The Carboxylate Anion of pyruvic acid is known as pyruvate. See also Gluconeogenesis, which carries out a process wherein glucose is synthesized rather than catabolized Alpha-ketoglutaric acid is one of two Ketone derivatives of Glutaric acid. The alanine formed is passed into the blood and transported to the liver. A reverse of the alanine aminotransferase reaction takes place in liver. Pyruvate regenerated forms glucose through gluconeogenesis, which returns to muscle through the circulation system. Gluconeogenesis (abreviated GNG) is a Metabolic pathway that results in the generation of Glucose from non- Carbohydrate carbon substrates such Glutamate in the liver enters mitochondria and degrades into ammonium ion through the action of glutamate dehydrogenase, which in turn participate in the urea cycle to form urea. In Cell biology, a mitochondrion (plural mitochondria) is a membrane-enclosed Organelle found in most eukaryotic cells. Ammonium is also an old name for the Siwa Oasis in western Egypt. Glutamate dehydrogenase is an Enzyme, present in Mitochondria of Eukaryotes, as are some of the other enzymes required for Urea synthesis that The urea cycle (also known as the ornithine cycle) is a cycle of biochemical reactions occurring in many animals that produces Urea ( N[[hydrogen Urea is an Organic compound with the Chemical formula ( N[[hydrogen H]]22 C[[oxygen O]] ^[4]

Glucose-alanine cycle enables pyruvate and glutamate to be removed from muscle and find their ways to liver. Glucose is able to be regenerated from pyruvate and returned to muscle. The energetic burden of gluconeogenesis is thus imposed on the liver instead of the muscle. All available ATP in muscle is devoted to muscle contraction. Adenosine-5'-triphosphate ( ATP) is a multifunctional Nucleotide that is most important as a " molecular currency" of intracellular Energy ^[4]

Link to hypertension

An international study led by Imperial College London found that people with high levels of alanine have higher blood pressure, energy intake, cholesterol levels, and body mass index. Imperial College London (officially The Imperial College of Science Technology and Medicine as given in its Royal Charter It is one of only three universities to have reached ^[5]

Chemical properties

Free radical stability

The deamination of an alanine molecule produces a stable alkyl free radical, CH₃C^•HCOO^–. In Chemistry, radicals (often referred to as free radicals) are atoms molecules or ions with Unpaired electrons on an otherwise Open shell Deamination can be induced in solid or aqueous alanine by radiation. ^[6]

This property of alanine is used in dosimetric measurements in radiotherapy. Radiation dosimetry is the calculation of the Absorbed dose in matter and tissue resulting from the exposure to Ionizing radiation. Radiation therapy (or radiotherapy) is the medical use of Ionizing radiation as part of Cancer treatment to control Malignant When normal alanine is irradiated, the radiation causes certain alanine molecules to become free radicals, and, as these radicals are stable, the free radical content can later be measured in order to find out how much radiation the alanine was exposed to. In this way, one can be assured that complex radiotherapy treatment plans will deliver the intended pattern of radiation dose.

References

See also

• carbamic acid
• glycine

External links

• Computational Chemistry Wiki

Carbamic acid is a compound that is unstable under normal circumstances Glycine (abbreviated as Gly or G) is the Organic compound with the formula NH2CH2COOH

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