2S3R2aminooctadecane13diol

2S,3R-2-aminooctanoic acid is a non-proteinogenic amino acid defined by an eight-carbon backbone and two stereocenters. The name indicates the absolute configurations at the second and third carbon atoms, respectively, corresponding to the α-carbon and the adjacent carbon in the chain. This stereochemical designation places the compound among chiral amino acids that can exist as multiple diastereomers.

Chemically, it features a primary amino group and a terminal carboxyl group attached to an eight-carbon chain. The α-carbon (C2) bears the amino and carboxyl groups as well as a hydrogen and the side chain, while C3 is another chiral center embedded in the extended carbon skeleton. The presence of two stereocenters allows several possible stereoisomers, including 2S,3R; other configurations such as 2R,3S, 2S,3S, and 2R,3R are theoretically possible depending on substitution patterns along the chain.

Synthesis and properties of 2S,3R-2-aminooctanoic acid are primarily of interest in organic and medicinal chemistry as a chiral building block for the construction of peptidomimetics and other chiral molecules. Preparation methods commonly involve asymmetric synthesis or resolution of racemic mixtures, with characterization by chiral chromatography, nuclear magnetic resonance, and mass spectrometry to confirm configuration.

Occurrence in nature is not well established, and the compound is largely described in the literature as a synthetic reagent or intermediate. In research contexts, it is used to explore enzyme specificity, stereochemical effects on activity, and the design of libraries for pharmaceutical development.