L-alanine

Alanine

Names
IUPAC name Alanine
Other names 2-Aminopropanoic acid
Identifiers
CAS Number	338-69-2 (D-isomer) Y 56-41-7 (L-isomer) Y 302-72-7 (racemic) Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:16977 N
ChEMBL	ChEMBL66693 Y
ChemSpider	64234 (D-isomer) Y 5735 (L-isomer) Y 582 (Racemic) Y
ECHA InfoCard	100.000.249
EC Number	206-126-4
IUPHAR/BPS	720
KEGG	C01401 N
PubChem	5950
UNII	1FU7983T0U N
InChI InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1 Y Key: QNAYBMKLOCPYGJ-UWTATZPHSA-N Y InChI=1/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6) Key: QNAYBMKLOCPYGJ-UHFFFAOYAA
SMILES O=C(O)C(N)C O=C(O)[C@@H](N)C
Properties
Chemical formula	C3H7NO2
Molar mass	89.09 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)
Acidity (pKa)	2.35 (carboxyl), 9.69 (amino)
Magnetic susceptibility (χ)	-50.5·10−6 cm3/mol
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Alanine (abbreviated as Ala or A; encoded by the codons GCU, GCC, GCA, and GCG) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH3⁺ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO⁻ form under biological conditions), and a side chain methyl group, classifying it as a nonpolar (at physiological pH), aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it.

The L-isomer (left-handed) of alanine is one of the 20 amino acids encoded by the human genetic code. L-Alanine is second only to leucine in rate of occurrence, accounting for 7.8% of the primary structure in a sample of 1,150 proteins. The right-handed form, D-Alanine occurs in bacterial cell walls and in some peptide antibiotics.

Alanine was first isolated in 1879 by Adolph Strecker. The amino acid was named in German, in reference to aldehyde, with the infix -an- for ease of pronunciation, the German ending used in chemical compounds being analogous to English -ine.

The α-carbon atom of alanine is bound to a methyl group (-CH₃), making it one of the simplest α-amino acids and also results in alanine's classification as an aliphatic amino acid. The methyl group of alanine is non-reactive and is thus almost never directly involved in protein function.

Alanine is an amino acid that cannot be phosphorylated, making it quite useful in a loss of function experiment with respect to phosphorylation.