Alanine

Alanine
	; Skeletal formula of L-alanine (neutral form)
Ball-and-stick model (zwitterionic form)	Space-filling model (zwitterionic form)
Names
	IUPAC name Alanine
	Systematic IUPAC name 2-Aminopropanoic acid
	Other names Alanic acid; Alaninic acid; 2-Aminopropionic acid
Identifiers
CAS Number	L: 56-41-7 ; D/L: 302-72-7 ; D: 338-69-2 ;
3D model (JSmol)	L: Interactive image; D: Interactive image; L Zwitterion: Interactive image; D Zwitterion: Interactive image;
3DMet	L: B00011;
Beilstein Reference	1720248
ChEBI	L: CHEBI:16977 ; D/L: CHEBI:16449; D: CHEBI:15570;
ChEMBL	L: ChEMBL279597 ;
ChemSpider	L: 5735 ; D/L: 582 ; D: 64234 ;
DrugBank	L: DB00160;
ECHA InfoCard	100.000.249
EC Number	L: 206-126-4;
Gmelin Reference	49628
IUPHAR/BPS	L: 720;
KEGG	L: C00041 ; D/L: C01401; D: C00133;
PubChem CID	L: 5950; D/L: 602; D: 71080;
UNII	L: OF5P57N2ZX ; D/L: 1FU7983T0U ; D: E3UDS4613U ;
CompTox Dashboard (EPA)	L: DTXSID20873899;
	InChI InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1 Key: QNAYBMKLOCPYGJ-REOHCLBHSA-N ; D/L: Key: QNAYBMKLOCPYGJ-UHFFFAOYSA-N; D: Key: QNAYBMKLOCPYGJ-UWTATZPHSA-N;
	SMILES L: C[C@@H](C(=O)O)N; D: C[C@H](C(=O)O)N; L Zwitterion: C[C@@H](C(=O)[O-])[NH3+]; D Zwitterion: C[C@H](C(=O)[O-])[NH3+];
Properties
Chemical formula	C3H7NO2
Molar mass	89.094 g·mol−1
Appearance	white powder
Density	1.424 g/cm3
Melting point	258 °C (496 °F; 531 K) (sublimes)
Solubility in water	167.2 g/L (25 °C)
log P	-0.68
Acidity (pKa)	2.34 (carboxyl; H2O); 9.87 (amino; H2O);
Magnetic susceptibility (χ)	-50.5·10−6 cm3/mol
Supplementary data page
	Alanine (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Alanine (symbol Ala or A),^[4] or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side chain. Consequently it is classified as a nonpolar, aliphatic α-amino acid. Under biological conditions, it exists in its zwitterionic form with its amine group protonated (as −NH₃⁺) and its carboxyl group deprotonated (as −CO₂⁻). It is non-essential to humans as it can be synthesized metabolically and does not need to be present in the diet. It is encoded by all codons starting with G C (GCU, GCC, GCA, and GCG).

The L-isomer of alanine (left-handed) is the one that is incorporated into proteins. L-alanine is second only to L-leucine in rate of occurrence, accounting for 7.8% of the primary structure in a sample of 1,150 proteins.^[5] The right-handed form, D-alanine, occurs in peptides in some bacterial cell walls^[6]^: 131 (in peptidoglycan) and in some peptide antibiotics, and occurs in the tissues of many crustaceans and molluscs as an osmolyte.^[7]

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1392. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ "L-alanine MSDS". ChemSrc.
^ Haynes WM, ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 978-1-4987-5428-6.
^ "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.
^ Doolittle RF (1989). "Redundancies in Protein Sequences". In Fasman GD (ed.). Prediction of Protein Structures and the Principles of Protein Conformation. New York: Plenum. pp. 599–623. ISBN 978-0-306-43131-9.
^ Mathews CK, Van Holde KE, Ahern KG (2000). Biochemistry (3rd ed.). San Francisco, CA: Benjamin/Cummings Publishing. ISBN 978-0-8053-3066-3. OCLC 42290721.
^ Yoshikawa N, Sarower MG, Abe H (2016). "Alanine Racemase and D-Amino Acid Oxidase in Aquatic Animals". In Yoshimura T, Nishikawa T, Homma H (eds.). D-Amino Acids: Physiology, Metabolism, and Application. Springer Japan. pp. 269–282. ISBN 978-4-431-56077-7.

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1392. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[chemsrc-2] "L-alanine MSDS". ChemSrc.

[CRC97-3] Haynes WM, ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 978-1-4987-5428-6.

[4] "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.

[5] Doolittle RF (1989). "Redundancies in Protein Sequences". In Fasman GD (ed.). Prediction of Protein Structures and the Principles of Protein Conformation. New York: Plenum. pp. 599–623. ISBN 978-0-306-43131-9.

[:0-6] Mathews CK, Van Holde KE, Ahern KG (2000). Biochemistry (3rd ed.). San Francisco, CA: Benjamin/Cummings Publishing. ISBN 978-0-8053-3066-3. OCLC 42290721.

[7] Yoshikawa N, Sarower MG, Abe H (2016). "Alanine Racemase and D-Amino Acid Oxidase in Aquatic Animals". In Yoshimura T, Nishikawa T, Homma H (eds.). D-Amino Acids: Physiology, Metabolism, and Application. Springer Japan. pp. 269–282. ISBN 978-4-431-56077-7.

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