Leucine

Leucine
	; Skeletal formula of L-leucine
Ball-and-stick model	Space-filling model
Names
	IUPAC name Leucine
	Other names 2-Amino-4-methylpentanoic acid
Identifiers
CAS Number	61-90-5 ;
3D model (JSmol)	Interactive image; Zwitterion: Interactive image;
ChEBI	CHEBI:15603 ;
ChEMBL	ChEMBL291962 ;
ChemSpider	5880 ;
DrugBank	DB00149 ;
ECHA InfoCard	100.000.475
IUPHAR/BPS	3312;
KEGG	D00030 ;
PubChem CID	6106;
UNII	GMW67QNF9C ;
CompTox Dashboard (EPA)	DTXSID9023203 ;
	InChI InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1 Key: ROHFNLRQFUQHCH-YFKPBYRVSA-N ; InChI=1/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1 Key: ROHFNLRQFUQHCH-YFKPBYRVBU;
	SMILES CC(C)C[C@@H](C(=O)O)N; Zwitterion: CC(C)C[C@@H](C(=O)[O-])[NH3+];
Properties
Chemical formula	C6H13NO2
Molar mass	131.175 g·mol−1
Acidity (pKa)	2.36 (carboxyl), 9.60 (amino)
Magnetic susceptibility (χ)	-84.9·10−6 cm3/mol
Supplementary data page
	Leucine (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Leucine (symbol Leu or L) is an essential amino acid that is used in the biosynthesis of proteins. Leucine is an α-amino acid, meaning 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 isobutyl group, making it a non-polar aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it: it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, and beans and other legumes. It is encoded by the codons UUA, UUG, CUU, CUC, CUA, and CUG.

Like valine and isoleucine, leucine is a branched-chain amino acid. The primary metabolic end products of leucine metabolism are acetyl-CoA and acetoacetate; consequently, it is one of the two exclusively ketogenic amino acids, with lysine being the other. It is the most important ketogenic amino acid in humans.

Leucine and β-hydroxy β-methylbutyric acid, a minor leucine metabolite, exhibit pharmacological activity in humans and have been demonstrated to promote protein biosynthesis via the phosphorylation of the mechanistic target of rapamycin (mTOR).

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