L-Isoleucine

L-Isoleucine was discovered in 1904 by Ehrlich, and its constitution established 3 years later by degradation to d-isoamylamine and by synthesis through the Strecker reaction with d-isovaleraldehyde.

IUPAC Name: (2S,3S)-2-Amino-3-methylpentanoic acid
Symbol: Ile or L
Molecular Weight: 131.17292 g/mol
Molecular Formula: C6H13NO2
Canonical SMILES: CCC(C)C(C(=O)O)N
Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)O)N
InChIKey Identifier: AGPKZVBTJJNPAG-JOOMIXNWDU
CAS Number: 73-32-5
MDL Number: MFCD00064222
Melting point: 286-288 °C
Solubility in water: 41.2 g/1 L (50 °C)
2D Molfile: Get the molfile
3D PDB file: Get the PDB file
Other names: (2S,3S)-alpha-Amino-beta-methyl-n-valeric acid; erythro-L-Isoleucine; L-iso-Leucine; (S)-Isoleucine; 2S,3S-Isoleucine

Load 3D Structure of Isoleucine

Isoleucine has two chiral centers; therefore there are four possible stereoisomers of isoleucine and two possible diastereomers of L-isoleucine. However, isoleucine present in nature exists in one enantiomeric form, (2S,3S)-2-amino-3-methylpentanoic acid.

Isoleucine can be synthesized in a multistep procedure starting from 2-bromobutane and diethylmalonate.

L-Isoleucine - an essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of Leucine. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.

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