D-3-Aminobutyric acid is a D-configured, non-proteinogenic amino acid with a four-carbon backbone bearing a primary amino group at the 3-position and a terminal carboxylic acid group, classifying it as an aliphatic amino acid. The side chain is a straight-chain alkyl (-CH2-CH2-CH3) that provides hydrophobic character without additional functional groups beyond the amino and carboxyl functionalities. As a free amino acid, it can be used as a substrate or building block in peptide and amino-acid derivative synthesis, as well as in structure-activity studies, chemical biology labeling strategies, and analytical method development where stereodefined amino acid standards are required.
CAT No: CP03002
CAS No:3775-73-3
Synonyms/Alias:3775-73-3;(R)-3-AminobutanoicAcid;(R)-3-AMINOBUTYRICACID;(3R)-3-aminobutanoicacid;D-3-Aminobutyricacid;R-3-Aminobutyricacid;(R)-beta-homo-alanine;(R)-3-Amino-butyricacid;(R)-HOMO-BETA-ALANINE;D--Homoalanine;AmbotzHAA8430;AC1NWJCQ;(3R)-3-Aminobutyricacid;SCHEMBL598845;MolPort-008-268-111;OQEBBZSWEGYTPG-GSVOUGTGSA-N;ACT05190;ZINC1713399;Butanoicacid,3-amino-,(3R)-;CA-612;MFCD00211284;AKOS005146085;AKOS015995185;CS19028;LS30206
D-3-Aminobutyric acid is a chiral amino acid with the stereogenic center at the β-position relative to the amino group, corresponding to the D-configuration. The molecule contains a primary amine and a carboxylic acid, enabling straightforward formation of salts, amides, esters, and protected derivatives used in amino acid chemistry. The zwitterionic character in aqueous media and the presence of both nucleophilic (amine) and electrophilic/activatable (carboxyl) functional groups make it suitable for coupling reactions and for incorporation into peptide-like frameworks. As a chiral building block, D-3-aminobutyric acid can serve as a stereodefined intermediate for downstream synthesis of β-substituted amino acid motifs and for stereochemical probes in chemical and biochemical research.
1. Peptide Coupling Building Block
D-3-Aminobutyric acid is applied in peptide synthesis workflows where β-amino acid incorporation is required to access D-configured, β-substituted peptide backbones. The amino and carboxyl functionalities support standard peptide coupling chemistry after appropriate protection strategies, such as temporary N-protection and carboxyl activation to form amide bonds. The D-stereocenter enables stereochemically defined incorporation that can be carried through to peptide analogs used for conformational studies and sequence-dependent property mapping. The resulting β-amino acid-containing peptides and peptidomimetic fragments can be used as research-grade intermediates for scaffold construction and for generating libraries of stereodefined analogs in synthetic peptide programs.
2. Unnatural Amino Acid Incorporation
D-3-Aminobutyric acid is utilized as an unnatural amino acid component in chemical biology and protein engineering contexts that require controlled perturbation of backbone geometry and side-chain placement. The β-position amino functionality allows construction of analogs that differ from canonical α-amino acid patterns, enabling systematic structure-activity relationship studies of backbone recognition and binding-site tolerance. Protecting-group strategies, including N-protection and carboxyl derivatization, can be employed to maintain chemoselectivity during multi-step synthesis and to support sequential fragment assembly. The D-configuration provides a stereodefined handle for generating stereochemical series, supporting downstream formation of labeled or functionalized peptide constructs used in mechanistic studies and molecular design campaigns.
3. Chiral Intermediate For Derivatization
D-3-Aminobutyric acid serves as a chiral amino acid intermediate for stereoselective derivatization into esters, amides, and N-protected derivatives used in fine chemical synthesis. The carboxylic acid can be converted into activated intermediates or protected forms to control reactivity during sequential functional group transformations, while the primary amine can be protected to enable selective chemistry at the acid or side-chain region. The D-stereocenter is retained through appropriately designed protection/deprotection sequences, supporting the preparation of enantiopure building blocks for downstream synthesis of β-amino acid derivatives, conformationally constrained analogs, and chiral ligands. The resulting intermediates can feed into broader synthetic programs that require stereodefined amino acid chemistry, including chiral scaffold elaboration and process-oriented intermediate preparation.
4. Analytical Reference And Labeling
D-3-Aminobutyric acid can be employed in analytical research as a chiral reference material for method development and stereochemical verification of β-amino acid-containing samples. The presence of both an amine and a carboxylic acid supports derivatization strategies for chromatographic detection, such as conversion to detectable ester or amide derivatives while preserving stereochemical integrity. Isotope-labeled or derivatized forms prepared from this D-building block can function as internal standards or tracer reagents in studies of amino acid metabolism pathways, peptide hydrolysis, or synthetic incorporation verification. The compound's defined stereochemistry and well-defined functional groups make it suitable for supporting analytical workflows that distinguish D- and related stereochemical variants in complex mixtures.
5. Pharmaceutical Intermediate Preparation
D-3-Aminobutyric acid is relevant to pharmaceutical intermediate preparation where β-amino acid motifs are incorporated into peptidomimetic or constrained peptide-like structures during lead optimization. The amino acid's bifunctional nature enables conversion into N-protected amino acid derivatives and activated carboxyl forms that participate in stepwise assembly of amide-linked fragments under controlled chemoselectivity. The D-configuration supports stereodefined synthesis of analog series used to probe backbone-dependent binding and stability characteristics during medicinal chemistry development. Downstream, the compound can be transformed into coupling-ready intermediates that integrate into larger synthetic routes for specialty active pharmaceutical ingredient fragments and related manufacturing intermediates.
6. Polymer And Material Functionalization
D-3-Aminobutyric acid can be applied in functional material and polymer modification programs where amino acid-derived repeat units or side-chain functionalities are introduced to tune polarity and chemical reactivity. The primary amine and carboxylic acid enable formation of amide or ester linkages to polymer backbones, surfaces, or crosslinkers after suitable protection and activation steps. The D-stereocenter may be used to impart stereochemical control to polymer-bound amino acid motifs, supporting materials that require defined chiral environments for binding or surface interaction studies. The resulting amino acid-functional materials can serve as intermediates for specialty chemical production, including chiral adsorption media, reactive surface coatings, and peptide-inspired functional polymers used in applied research and industrial development.
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