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Encyclopedia > Alanine

Chemical structure of L-alanine Image File history File links L-alanine-skeletal. ... Image File history File links Download high-resolution version (859x746, 29 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Alanine Alanine (data page) User:Benjah-bmm27/Old gallery ...

Alanine
Systematic (IUPAC) name
(S)-2-aminopropanoic acid
Identifiers
CAS number 56-41-7
PubChem         5950
Chemical data
Formula C3H7NO2 
Mol. weight 89.1
SMILES C[C@H](N)C(O)=O
Complete data

Alanine (Ala, A) also 2-aminopropanoic acid is a non-essential α-amino acid. It exists as two distinct enantiomers - L-alanine and D-alanine. L-alanine is one of the 20 amino acids most widely used in protein synthesis, second to leucine, accounting for 7.8% of the primary structure in a sample of 1,150 proteins [1]. D-alanine occurs in bacterial cell walls and in some peptide antibiotics. IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... PubChem is a database of chemical molecules. ... This article does not cite its references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass 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). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Physical properties Hazard properties Flash point - N/A R/S statement R: N/A S: N/A RTECS number: N/A Chemical properties Pharmacological properties OrganicBox_complete References a  206-418-1 EINECS for D-alanine a  200-273-8 EINECS for L-alanine a  PubChem 602 a  PubChem 5950 This... Phenylalanine is one of the standard amino acids. ... In chemistry two stereoisomers are said to be enantiomers if one can be superimposed on the mirror image of the other, and vice versa. ... An overview of protein synthesis. ... Leucine is one of the 20 most common amino acids and coded for by DNA. It is isomeric with isoleucine. ... A protein primary structure is a chain of amino acids. ... A representation of the 3D structure of myoglobin, showing coloured alpha helices. ...

Contents

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 refers to the first carbon after the carbon that attaches to the functional group. ... In chemistry, aliphatic compounds are organic compounds in which carbon atoms are joined together in straight or branched chains. ...


Biosynthesis

Alanine is most commonly made by reductive amination of pyruvate. Because transamination reactions are readily reversible, alanine can be easily formed from pyruvate and thus has close links to metabolic pathways such as glycolysis, gluconeogenesis, and the citric acid cycle. Reductive amination is a type of amination reaction which involves the conversion of a carbonyl group to an amine. ... Pyruvate (CH3COCOO−) is the ionized form of pyruvic acid. ... Transamination is the reaction between an amino acid and an alpha-keto acid. ... Glycolysis is a metabolic pathway by which a 6-carbon glucose (Glc) molecule is oxidized to two molecules of pyruvic acid (Pyr). ... Pyruvic acid Oxaloacetic acid Phosphoenolpyruvate Fructose 1,6-bisphosphate Fructose 6-phosphate Glucose-6-phosphate Glucose Gluconeogenesis is the generation of glucose from non-sugar carbon substrates like pyruvate, lactate, glycerol, and amino acids (primarily alanine and glutamine). ... Overview of the citric acid cycle The citric acid cycle (also known as the tricarboxylic acid cycle, the TCA cycle, or the Krebs cycle, after Hans Adolf Krebs who identified the cycle) is a series of chemical reactions of central importance in all living cells that use oxygen as part...


Function

The methyl group of alanine is very non-reactive, and is thus rarely directly involved in protein function. However, alanine can play a role in substrate recognition or specificity, particularly in interactions with other non-reactive atoms such as carbon.


It goes through alanine cycle to generate glucose from protein. The alanine cycle is quite similar to the Cori cycle. ...


Sources

Any protein-containing food such as meat, poultry, fish, eggs or dairy products is rich in alanine.


References

  1. a  Doolittle RF (1989). "Redundancies in protein sequences" in Prediction of Protein Structures and the Principles of Protein Conformation. (Fasman GD, ed.), pp 599-623, Plenum Press, New York.

External links

  • Computational Chemistry Wiki
  • Links to external chemical sources


v • d • e
Major Families of Biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids: The 20 Common Amino Acids Analogues of nucleic acids:
Alanine (dp) | Arginine (dp) | Asparagine (dp) | Aspartic acid (dp) | Cysteine (dp) | Glutamic acid (dp) | Glutamine (dp) | Glycine (dp) | Histidine (dp) | Isoleucine (dp) | Leucine (dp) | Lysine (dp) | Methionine (dp) | Phenylalanine (dp) | Proline (dp) | Serine (dp) | Threonine (dp) | Tryptophan (dp) | Tyrosine (dp) | Valine (dp)

  Results from FactBites:
 
Alanine information page. All about alanine and the role it plays in your diet. (470 words)
Alanine is a non-essential amino acid and is used by the body to build protein and was first isolated in 1879.
The alpha-carbon in alanine is substituted with a levorotatory (l)-methyl group, making it one of the simplest amino acids with respect to molecular structure and is one of the most widely used in protein construction.
In one study of men with benign prostatic hyperplasia, it was found that 780 mg of alanine per day for two weeks and then 390 mg for the next two and a half months, taken together in combination with equal amounts of glycine and glutamic acid reduced the symptoms.
  More results at FactBites »


 
 

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