L-2-Aminobutyric acid is a free, naturally occurring amino acid featuring a four-carbon backbone with an amino group at the 2-position and a terminal carboxylic acid, classed as a branched aliphatic (non-aromatic) amino acid. The side chain is a short alkyl substituent (isopropyl-like/β-methyl) that bears no additional functional groups beyond hydrocarbon character, and the "L-" designation indicates a specific stereochemical configuration at the α-carbon. As a substrate and building block in peptide and amino acid derivative synthesis, it can be incorporated into peptides or used to prepare labeled or structurally modified amino acid analogues for structure-activity studies, conformational analysis, and analytical method development.
CAT No: CP02902
CAS No:1492-24-6
Synonyms/Alias:L-2-Aminobutyricacid;(S)-2-Aminobutanoicacid;1492-24-6;(2S)-2-aminobutanoicacid;L-alpha-Aminobutyricacid;(S)-(+)-2-AminobutyricAcid;(S)-2-Amino-butyricacid;L-(+)-2-aminobutyricacid;2S-amino-butanoicacid;(S)-2-Aminobutyricacid;(-)-2-Aminobutyricacid;L-alpha-Aminobutyrate;L-alpha-Amino-n-butyricacid;L-Butyrine;(S)-2-Aminobutanoate;L-Ethylglycine;S-Butyrine;2-Aminobutanoate;l-2-amino-n-butyricacid;2S-amino-butanoate;h-2-abu-oh;L-a-aminobutyricacid;L-2-Aminobuttersaeure;(+)-2-Aminobutanoate;(S)-2-amino-Butanoate
L-2-Aminobutyric acid is a chiral, non-proteinogenic amino acid featuring an L-configured stereocenter at the alpha-carbon and a secondary amino group paired with a carboxylic acid functionality. The side chain is a short ethyl substituent that lacks additional heteroatoms, which makes its derivatization chemistry largely governed by protecting-group selection for the amine and carboxylate. The compound can be converted into amino acid esters or N-protected derivatives to tune solubility, control reactivity during peptide coupling, and support selective transformations at either the amine or the acid. L-2-Aminobutyric acid also functions as a chiral building block and biochemical research intermediate for constructing constrained peptide motifs and for generating stereochemically defined analogs.
1. Peptide Synthesis
L-2-Aminobutyric acid is applied in peptide synthesis as a non-natural amino acid building block for assembling sequence-defined peptides and peptide fragments. The alpha-amino and alpha-carboxyl groups can be protected as N-protected amino acid derivatives and converted to activated carboxyl forms, enabling standard peptide coupling strategies while preserving the L stereochemistry. The compact side chain can be incorporated to modulate backbone sterics and local conformational preferences, which is useful for constructing peptide analogs and for studying how subtle side-chain changes affect coupling outcomes and downstream stability. L-2-Aminobutyric acid supports iterative protected amino acid chemistry that feeds into solid-phase or solution-phase peptide construction workflows.
2. Amino Acid Derivatization
L-2-Aminobutyric acid is suitable for amino acid derivatization workflows that prepare esters, amides, and N-substituted derivatives for downstream synthetic use. The carboxylic acid can be masked as an ester to adjust handling properties during synthesis, while the amine can be protected to control chemoselectivity during functional group transformations. The resulting derivatives can serve as intermediates for further modification, including conversion to activated intermediates for C-terminal or side-chain functionalization strategies that rely on orthogonal protection. L-2-Aminobutyric acid therefore functions as a chiral precursor for fine chemical synthesis routes that require stereodefined amino acid functionality.
3. Chemical Biology Probes
L-2-Aminobutyric acid is used in chemical biology research to generate stereochemically defined amino acid analogs for probing biomolecular recognition and peptide-mediated interactions. The L configuration at the alpha-carbon and the presence of both amine and acid functionalities enable incorporation into peptide scaffolds that can be further functionalized for labeling or affinity-tag attachment. N-protected and activated forms of L-2-Aminobutyric acid can be incorporated into peptide constructs to introduce a non-proteinogenic residue that may alter hydrogen-bonding patterns and backbone dynamics without adding additional side-chain heteroatoms. L-2-Aminobutyric acid thus supports the preparation of biochemical research intermediates used in molecular design and structure-function studies.
4. Chiral Building Block Development
L-2-Aminobutyric acid serves as a chiral amino acid intermediate for stereoselective synthesis programs that require retention or controlled transformation of the alpha stereocenter. The amino acid framework enables conversion into chiral derivatives such as N-protected amino acid esters and activated carboxylic acid intermediates that participate in coupling chemistry while maintaining stereochemical integrity. The compact ethyl side chain can be used to build constrained analog libraries where steric effects arise primarily from the backbone and side-chain geometry rather than from additional functional groups. L-2-Aminobutyric acid can therefore be employed as a starting chiral material for producing stereodefined intermediates used in peptide science, chiral synthesis, and applied molecular scaffold generation.
5. Pharmaceutical Intermediate Preparation
L-2-Aminobutyric acid is relevant to pharmaceutical intermediate preparation where non-proteinogenic amino acid residues are incorporated into peptide-like or constrained peptidomimetic structures. The amine and carboxyl groups can be protected and activated to support controlled assembly of fragments that later undergo deprotection and purification steps typical of fine chemical manufacturing. Side-chain simplicity can reduce competing side reactions during scale-up while still enabling stereochemically defined incorporation into larger synthetic sequences. L-2-Aminobutyric acid can be applied as a process chemistry intermediate for producing amino acid building blocks used in the manufacture of peptide analogs and related research-grade intermediates.
6. Industrial Chemical Manufacturing
L-2-Aminobutyric acid can be utilized in industrial chemical manufacturing contexts as a feedstock for producing protected amino acid derivatives used across specialty chemical production. The ability to form amino acid esters and N-protected intermediates supports downstream processing that requires controlled reactivity, improved solubility, and compatibility with coupling reagents and purification operations. The stereodefined L configuration makes the compound suitable for routes that demand consistent chiral input for generating amino acid building blocks at scale. L-2-Aminobutyric acid therefore functions as an amino acid-based intermediate that bridges chiral synthesis and industrial peptide-building chemistry.
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