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22-AUGUST-2008 06:13:22 - Alanine 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 89.1 g/mol SMILES CC@HNCO=O Complete data Alanine abbreviated as Ala or A1 is an α-amino acid with the chemical formula HO2CCHNH2CH3. The L-isomer is one of the 20 proteinogenic amino acids, i.e. the building blocks of proteins. 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 7.8% of the primary structure in a sample of 1,150 proteins.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 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. 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. 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 generates glucose from protein via the alanine cycle. 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.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. In muscle and other tissues that degrade amino acids for fuel, amino groups are collected in the form of glutamate by transamination. 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. 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. 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.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.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.5 Chemical properties Free radical stability The deamination of an alanine molecule produces a stable alkyl free radical, CH3CHCOO-. Deamination can be induced in solid or aqueous alanine by radiation.6 This property of alanine is used in dosimetric measurements in radiotherapy. When normal alanine is irradiated, the radiation causes certain alanine molecules to become free radicals, and, as these radicals are stable, the free radical contentcitation needed 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 ^ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. Nomenclature and Symbolism for Amino Acids and Peptides. Recommendations on Organic Biochemical Nomenclature, Symbols Terminology etc. Retrieved on 2007-05-17. ^ Doolittle, R. F.; Fasman G.D. ed. 1989. Redundancies in protein sequences in Prediction of Protein Structures and the Principles of Protein Conformation. New York: Plenum Press, pp. 599-623. ^ Kendall, E. C.; McKenzie, B. F. dl-Alanine Organic Syntheses, Collected Volume 1, p.21 1941. http://www.orgsyn.org/orgsyn/pdfs/CV1P0021.pdf ^ a b Nelson, D. L. Cox, M. M. 2005. Lehninger Principles of Biochemistry, 4th ion. New York: W. H. Freeman and Company, pp. 684-685. ISBN 0-7167-4339-6. ^ 'Metabolic fingerprint' linked to high blood pressure - Telegraph ^ Journal of Radioanalytical and Nuclear Chemistry, 1998, 2321-2, pp. 139-141. DOI 10.1007/BF02383729 http://www.springerlink.com/content/j050542210k251ru/ See also carbamic acid glycine External links Computational Chemistry Wiki v d e The 20 Common Amino Acids dp = data page Branched-chain amino acids Isoleucine dp | Leucine dp | Valine dp Non Branch-chain Alanine dp | Arginine dp | Asparagine dp | Aspartic acid dp | Cysteine dp | Glutamic acid dp | Glutamine dp | Glycine dp | Histidine dp | Lysine dp | Methionine dp | Phenylalanine dp | Proline dp | Serine dp | Threonine dp | Tryptophan dp | Tyrosine dp Other classifications Essential amino acids | Ketogenic amino acid | Glucogenic amino acid Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Alanine Categories: Proteinogenic amino acids | Glucogenic amino acidsHidden categories: All articles with statements | Articles with statements since March 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Català Česky Dansk Deutsch Ελληνικά Español Esperanto Français Galego Hrvatski Bahasa Indonesia Italiano עברית LatvieÅ¡u Lëtzebuergesch Lietuvių Magyar Nederlands 日本語 پښتو Polski Português Română РуÑ?Ñ?кий SlovenÄ?ina СрпÑ?ки / Srpski Basa Sunda Suomi Svenska Türkçe УкраїнÑ?ька This page was last modified on 15 June 2008, at 12:38
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