2-Amino isobutyric acid contains an amino group and a carboxyl group on a branched, aliphatic backbone derived from isobutyric acid, classifying it as a non-standard, non-proteinogenic amino acid with a highly substituted side chain. The side chain bears additional methyl substituents that increase steric bulk and hydrophobic character relative to less substituted amino acids, and the molecule exists as a free amino acid in its unprotected form with no additional functional handles beyond the primary amino and carboxyl functionalities. In peptide and peptidomimetic synthesis, it is used as a structural building block to introduce steric effects and altered side-chain properties into amide linkages, and it can also serve as a reference or substrate analog in analytical and chemical biology studies focused on amino acid structure-property relationships.
CAT No: CP03901
CAS No:62-57-5
Synonyms/Alias:3-(2-Thienyl)-D-alanine;62561-76-6;(R)-2-amino-3-(thiophen-2-yl)propanoicacid;D-2-THIENYLALANINE;(2R)-2-amino-3-thiophen-2-ylpropanoicacid;(2R)-2-azanyl-3-thiophen-2-yl-propanoicacid;beta-(2-Thienyl)-D-alanine;PubChem18712;H-D-Thi-OH;AC1OG7CN;beta-2-thienyl-D-alanine;a-(2-thienyl)-D-alanine;3-(2-thiophenyl)-D-alanine;BIDD:GT0430;SCHEMBL288244;beta-(2-thiophenyl)-D-alanine;CHEBI:77819;CTK8F8097;MolPort-001-758-811;WTOFYLAWDLQMBZ-ZCFIWIBFSA-N;CS-M2655;ZINC4141712;KM0633;AKOS012010222;AKOS015854101
2-Amino isobutyric acid is a branched aliphatic amino acid featuring a secondary amino group and a sterically constrained isobutyl side chain, commonly encountered as a non-proteinogenic building block in chemical and analytical workflows. Its small, hydrophobic structure makes it useful for preparing defined amino acid mixtures, standards, and synthetic intermediates where minimal side-chain functionality is advantageous. Researchers also use it as a structurally informative component in peptide and peptidomimetic design contexts that require a compact, branched residue.
1. Peptidomimetic Building Blocks
2-Amino isobutyric acid is used as a compact amino acid building block for peptidomimetic and constrained peptide analog synthesis, where a branched side chain can help modulate local sterics and backbone presentation without introducing additional reactive functionality. Medicinal chemistry groups and custom peptide synthesis providers often incorporate this residue into short analogs and library members to probe structure-property relationships, including how side-chain branching influences conformational preferences and chemical behavior during downstream derivatization. Because the molecule is relatively simple and non-functionalized beyond the amino and carboxyl groups, it is frequently selected when a defined, low-complexity residue is needed for systematic comparison across analog series.
2. Amino Acid Mixture Standards
2-Amino isobutyric acid is routinely employed in analytical chemistry workflows that require accurate amino acid composition reference materials, including calibration and verification of amino acid profiling methods. Analytical laboratories use it to prepare defined amino acid standard mixtures for chromatography-based assays and for method development where branched amino acids must be resolved and quantified consistently. Its well-defined structure supports reproducible preparation of internal or external standards, particularly in studies that benchmark sample processing and instrument performance for amino acid panels, including targeted quantitation approaches where each component's identity and mass/retention behavior must be controlled.
3. Stable Isotope Method Development
2-Amino isobutyric acid is leveraged in method development and tracer-adjacent workflows where branched amino acid behavior needs to be characterized under specific extraction and derivatization conditions. Analytical groups preparing LC-MS or GC-MS workflows often include this amino acid in qualification sets to evaluate recovery, derivatization efficiency (when applicable), and chromatographic separation relative to other closely related amino acids. In stable isotope research contexts, it also serves as a structurally relevant unlabeled reference component for building calibration strategies and for checking background contributions when labeled analogs are analyzed in parallel.
4. Pharmaceutical Intermediate Synthesis
2-Amino isobutyric acid is used as a practical starting material for downstream preparation of amino acid-derived intermediates in specialty chemical and pharmaceutical intermediate development programs. Process and R&D chemists select it when a small branched amino acid scaffold is needed to introduce an amino acid motif into larger synthetic targets, including intermediates for peptidomimetic scaffolds and related nitrogen-containing building blocks. Its straightforward functionality supports incorporation into protected or activated derivatives during intermediate assembly, enabling controlled downstream coupling steps in custom synthesis programs where residue identity must be maintained through multistep sequences.
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