D-2-Aminobutyric acid

D-2-Aminobutyric acid is a chiral amino acid with the side chain CH2CH3 and the stereogenic center at the alpha carbon, giving a D-configuration that influences incorporation outcomes in peptide and biomolecule contexts. The molecule contains a primary amino group and a carboxylic acid, enabling standard amino acid coupling chemistry while also supporting salt formation and controlled solubility for handling. The relatively small, aliphatic side chain provides a sterically modest but stereochemically defined residue that can modulate conformations in short peptides and peptidomimetic scaffolds. As an amino acid building block and chiral intermediate, D-2-aminobutyric acid can be converted into protected derivatives, activated esters, or coupling-ready forms for downstream synthesis.

1. Peptide Synthesis

D-2-Aminobutyric acid is applied in peptide building block preparation where stereodefined incorporation at the alpha position is required for conformational control. The amino and carboxyl functionalities can be protected and activated to participate in amide bond formation using standard peptide coupling strategies, while the aliphatic side chain supports incorporation into hydrophobic segments. D-configuration retention is relevant for peptide analogs, including short sequence variants used to probe backbone stereochemistry and side-chain packing. Downstream use includes generating D-2-aminobutyric acid-containing peptides for structure-activity relationship studies and for building stereochemically defined peptide libraries.

2. Chiral Synthesis Intermediate

D-2-Aminobutyric acid serves as a chiral amino acid intermediate for asymmetric synthesis planning and for manufacturing routes that require a D-configured carbon center. The primary amine and carboxylic acid allow conversion into protected amino acid derivatives, including N-protected forms and activated acid derivatives, which can be carried through multi-step sequences without losing the stereochemical information. The small aliphatic framework can be used to access other chiral intermediates via functional group transformations of the side chain or via derivatization of the amino and acid groups. Industrially, the compound can be employed in fine chemical synthesis as a stereochemical feedstock for downstream chiral building blocks.

3. Amino Acid Derivatization

D-2-Aminobutyric acid is suitable for amino acid derivatization workflows that require controlled reactivity of the amino and carboxyl groups. The carboxylic acid can be esterified to form amino acid esters for improved handling and for enabling selective transformations, while the amine can be protected to direct chemoselective modifications. Derivatization can generate coupling-ready intermediates, chromatographically manageable forms, or functionalized derivatives that support further side-chain or backbone modifications. Resulting products include activated intermediates used in peptide coupling chemistry, as well as stereochemically defined substrates for synthetic organic chemistry campaigns.

4. Chemical Biology Probes

D-2-Aminobutyric acid is utilized in chemical biology research where incorporation of a D-amino acid residue helps tune peptide stability and stereochemical recognition. The D-configured alpha carbon and aliphatic side chain can be embedded into peptide constructs to create defined stereochemical patterns for studying molecular recognition, binding-site geometry, and backbone-dependent conformational preferences. The amino acid's functional groups enable preparation of labeled or conjugatable peptide analogs through protected intermediate strategies and subsequent deprotection or functional group activation. Downstream applications include generating stereochemically defined probes for assays that monitor peptide interactions and for comparative studies across stereoisomeric amino acid substitutions.

5. Pharmaceutical Manufacturing

D-2-Aminobutyric acid is relevant to pharmaceutical manufacturing contexts where chiral amino acid intermediates are required for synthesis of peptide-like building blocks and related active ingredient precursors. The presence of both an amino group and a carboxylic acid supports conversion into protected or activated forms that are compatible with controlled coupling steps in process chemistry. The small, aliphatic residue can be incorporated into intermediate peptides or peptidomimetic fragments used during route development and scale-up, with stereochemical integrity maintained through appropriate protection and activation sequences. Industrially, the compound can function as a stereochemically defined input for specialty chemical production where chiral consistency and reproducible coupling behavior are required.

6. Analytical Research Standards

D-2-Aminobutyric acid is applied in analytical research as a stereochemically defined amino acid standard and calibration component for method development. The defined D-configuration and intact amino acid functionality support use in chromatographic and mass spectrometric workflows aimed at distinguishing stereoisomeric amino acids and monitoring derivatized amino acid profiles. Derivative formation from the amino and acid groups can enable consistent analytical detection and improved ionization behavior for targeted quantitation. Downstream use includes supporting quality control of amino acid derivative intermediates and verifying stereochemical outcomes in synthetic and peptide construction processes.

1. Myotropic activity of allatostatins in tenebrionid beetles

2. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate

3. The spatiotemporal control of signalling and trafficking of the GLP-1R

4. High fat diet and GLP-1 drugs induce pancreatic injury in mice

5. Characterization of Novel P-Selectin Targeted Complement Inhibitors in Murine Models of Hindlimb Injury and Transplantation