Alanines

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Chemical structure of L-alanine
Alanines
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 is an α-amino acid with the chemical formula HO₂CCH(NH₂)CH₃. The L-isomer is one of the 20 proteinogenic amino acids, i.e. the building blocks of proteins. Its three letter code is ala, its one letter code is A, and its codons are GCU, GCC, GCA, and GCG.^[1] It is classified as an nonpolar amino acid. L-alanine is second only 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.

Contents 1 Structure 2 Biosynthesis 3 Sources 4 See also 5 References 6 External links

[edit] 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 methyl group of alanine is non-reactive and is thus almost never directly involved in protein function.

[edit] Biosynthesis

Alanine is most commonly produced by reductive amination of 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. It also arises together with lactate and generate glucose from protein via the alanine cycle.

[edit] Sources

Any protein-containing food such as meat, poultry, fish, eggs or dairy products is rich in alanine. Racemic alanine can be prepared via the addition of hydrogen cyanide and ammonia to acetaldehyde by the Strecker reaction.^[2]

[edit] See also

• Phenylalanine
• Beta-alanine

[edit] 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.

1. ↑ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. Nomenclature and Symbolism for Amino Acids and Peptides. Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. URL accessed on 2007-05-17.
2. ↑ Kendall, E. C.; McKenzie, B. F. “dl-Alanine” Organic Syntheses, Collected Volume 1, p.21 (1941).http://www.orgsyn.org/orgsyn/pdfs/CV1P0021.pdf

[edit] External links

• Computational Chemistry Wiki

Amino acids

Alanine | Arginine | Asparagine | Aspartic acid | Cysteine | Glutamic acid | Glutamine | Glycine | Histidine | Isoleucine | Leucine | Lysine | Methionine | Phenylalanine | Proline | Serine | Threonine | Tryptophan | Tyrosine | Valine

Essential amino acid | Protein | Peptide | Genetic code

This page uses content from the English-language version of Wikipedia. The original article was at Alanine. The list of authors can be seen in the page history. As with Psychology Wiki, the text of Wikipedia is available under the GNU Free Documentation License.