Boc-2-Aminoisobutyric acid is a protected amino acid derivative in which 2-aminoisobutyric acid is masked at the amino functionality by a tert-butoxycarbonyl (Boc) protecting group. The molecule contains a free carboxylic acid and a side-chain characteristic of 2-aminoisobutyric acid, with a stereocenter at the 2-position implied by the amino acid backbone but not specified in the provided name. In peptide and amino acid synthesis workflows, the Boc group supports chemoselective handling of the amino group while the carboxyl functionality remains available for coupling steps, making the compound a precursor to further protected amino acid building blocks and related peptide derivatives.
CAT No: CP03902
CAS No:30992-29-1
Synonyms/Alias:30992-29-1;Boc-Aib-OH;Boc-alpha-methylalanine;N-Boc-2-aminoisobutyricacid;2-(Boc-amino)isobutyricAcid;2-((tert-butoxycarbonyl)amino)-2-methylpropanoicacid;N-Boc-2-Aminoisobutanoicacid;N-Boc-alpha-methylalanine;N-Boc-2-amino-2-methylpropanoicacid;alpha-(Boc-amino)isobutyricacid;MFCD00042973;SBB069099;2-[(tert-butoxycarbonyl)amino]-2-methylpropanoicacid;N-(tert-butoxycarbonyl)-2-methylalanine;2-tert-butoxycarbonylamino-2-methylpropionicacid;N-[(1,1-Dimethylethoxy)carbonyl]-2-methyl-alanine;N-((1,1-Dimethylethoxy)carbonyl)-2-methyl-alanine;2-[(tert-butoxy)carbonylamino]-2-methylpropanoicacid;N-([(1,1-dimethylethyl)oxy]carbonyl}-2-methylalanine;N-{[(1,1-dimethylethyl)oxy]carbonyl}-2-methylalanine;EINECS250-421-0;zlchem202;AC1MBZSO;PubChem16475;ACMC-209hjt
Boc-2-Aminoisobutyric acid is a Boc-protected amino acid building block featuring the sterically hindered 2-aminoisobutyric acid side chain, commonly used in peptide chemistry to introduce a compact, conformationally informative residue. The tert-butoxycarbonyl (Boc) group provides acid-stable protection for the amino functionality during synthesis and subsequent coupling steps, making it a practical intermediate for preparing protected peptide segments and nonproteinogenic amino acid-containing sequences. Its hindered backbone environment is frequently leveraged in medicinal chemistry and peptide optimization workflows where side-chain sterics and backbone substitution patterns are important.
1. Peptide Segment Building
Boc-2-Aminoisobutyric acid is used by peptide synthesis groups to assemble protected peptide segments that incorporate the 2-aminoisobutyric acid residue. The Boc-protected amino group supports stepwise construction workflows in solution-phase or protected-segment strategies, where the residue is introduced as a defined, stereochemically consistent building unit. Researchers often select this scaffold to modulate local steric environment and influence how a peptide sequence accommodates backbone substitution, which is particularly relevant in the development of peptidomimetic structures and structure-activity relationship (SAR) libraries.
2. Nonproteinogenic Residue Incorporation
Boc-2-Aminoisobutyric acid serves as a practical building block for introducing a nonproteinogenic amino acid motif into custom peptides designed for chemical biology and medicinal chemistry studies. Its compact, branched side chain provides a distinct steric pattern compared with standard aliphatic residues, enabling developers to probe how changes in side-chain bulk and backbone substitution affect peptide conformation and functional readouts in downstream assays. Chemical biology teams and peptide medicinal chemists commonly rely on such protected amino acid intermediates to generate sequence-defined analogs for SAR mapping and optimization of peptide-like scaffolds.
3. Pharmaceutical Intermediate Development
Boc-2-Aminoisobutyric acid is also used as a pharmaceutical intermediate in specialty chemical manufacturing where protected amino acid derivatives are required as controlled inputs for further derivatization. Process development and intermediate synthesis teams value the Boc-protected format because it offers a stable protected amino functionality that can be carried through multi-step assembly toward higher-complexity targets, including protected peptide fragments and amino acid-derived intermediates. This product format is particularly relevant when downstream workflows require a defined amino acid unit with a hindered side chain that can be incorporated into larger synthetic sequences with consistent stoichiometry.
4. Protected Amino Acid Library Synthesis
Boc-2-Aminoisobutyric acid is frequently selected for building protected amino acid libraries used in research-scale peptide analog generation. By using a single, well-defined Boc-protected residue, researchers can standardize the incorporation of the 2-aminoisobutyric acid motif across multiple analogs, improving comparability between variants prepared for screening, binding studies, or mechanistic chemical biology experiments. Peptide-focused discovery groups and custom synthesis providers use this type of protected building block to streamline the preparation of sequence-defined materials where the steric characteristics of the residue are a key design variable.
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