D-2,4-Diaminobutyric acid is a D-configured non-proteinogenic amino acid featuring a four-carbon backbone that bears two amino substituents at the 2- and 4-positions, classifying it as a diamino amino acid. The molecule contains a free carboxyl group and two primary amine functional groups, providing a strongly basic, polycationic side-chain character that can participate in salt formation and electrostatic interactions. In peptide and amino acid derivative synthesis, it is used as a chemically defined building block for introducing a diamino functionality into sequences and for structure-activity or chemical biology studies that require a distinct side-chain charge pattern.
CAT No: CP05301
CAS No:26908-94-1
Synonyms/Alias:(R)-2,4-Diaminobutanoicacid;26908-94-1;D-2,4-Diaminobutyricacid;UNII-08TNR2VVMT;08TNR2VVMT;D-Dab.2hydrochloride;AmbotzHAA1179;PubChem14751;H-D-Dab-OH?2HCl;AC1LCVS3;KSC914O6R;SCHEMBL288792;(r)-2,4-diaminobutyricacid;2,4-Diaminobutyricacid,D-;CHEMBL102493;D-2,4-diamino-N-butyricacid;(2R)-2,4-diaminobutanoicacid;CTK8B4768;d-alpha,gamma-diaminobutyricacid;MolPort-008-267-982;2,4-Diaminobutanoicacid,(d)-;ACT04325;Butyricacid,2,4-diamino-,D-;ANW-46126;ZINC53122793
D-2,4-Diaminobutyric acid is a D-configured amino acid featuring a four-carbon backbone bearing two primary amino groups at the 2- and 4-positions, along with a carboxylic acid functionality. The molecule's stereochemistry defines the chiral center at C-2, while the additional side-chain amine increases hydrogen-bonding capacity and enables dense functionalization chemistry. As an amino acid derivative in free form, it can participate in peptide coupling through its carboxyl group while the diamine side chain can be protected or selectively deprotected to manage chemoselectivity. The strongly basic amine pair and the carboxylic acid create a reactivity profile suited to protected amino acid synthesis, orthogonal protection design, and downstream conversion into peptidic or heterocycle-containing scaffolds.
1. Protected Diaminobutyric Building Blocks
D-2,4-Diaminobutyric acid supports protected amino acid synthesis workflows where selective N-protection is used to control which amine participates in peptide coupling versus which remains available for side-chain derivatization. The carboxylic acid enables standard amide bond formation to generate peptide building blocks, while the two primary amines can be differentially protected to enable orthogonal deprotection strategies during stepwise assembly. The D-configuration at the backbone stereocenter helps preserve stereochemical integrity through coupling and deprotection sequences. Protected derivatives prepared from this diamino acid can serve as intermediates for peptide analog construction and for producing defined amino acid sequences containing an extra basic side chain.
2. Peptide Coupling And Backbone Incorporation
D-2,4-Diaminobutyric acid is applicable in peptide synthesis and peptidomimetic construction where a diamino side chain is used to modulate charge, binding interactions, and conformational behavior. The amino acid framework provides a coupling handle through the carboxyl group, and the additional 4-position amine can be protected to prevent undesired crosslinking or side reactions during iterative coupling cycles. The chiral D-center allows incorporation into sequences that require stereodefined residues, including unnatural amino acid placements for structure-activity relationship studies. Downstream, the installed diamine functionality can be retained for cationic recognition motifs or transformed into further functional groups after peptide assembly.
3. Chemical Biology Substrate Design
D-2,4-Diaminobutyric acid can be employed in chemical biology research as a charged amino acid component for designing enzyme substrates, inhibitors, or binding probes that rely on amine-mediated recognition. The side-chain primary amine provides a handle for derivatization into fluorescent tags, affinity groups, or reactive warheads, while the carboxyl-derived incorporation can position the diamine within a peptide-like context for controlled presentation. Stereochemical control at the D-backbone can be relevant for assessing stereospecific enzyme preferences or for generating probes with altered binding geometry. The resulting labeled or functionalized derivatives can serve as intermediates for biochemical investigation and for mapping molecular recognition features involving basic residues.
4. Bioconjugation And Cationic Linkers
D-2,4-Diaminobutyric acid is suitable for bioconjugation chemistry where the diamine motif is used to create positively charged linkers or conjugation-ready intermediates. The presence of two primary amines enables selective functional group installation, including conversion into activated intermediates for amide formation, urea/thiourea formation, or coupling to electrophilic biomolecule-reactive handles after appropriate protection management. The carboxylic acid can be converted into activated ester or amide-forming derivatives in downstream synthesis to connect the diamino acid to carrier proteins, peptides, or polymer backbones. D-stereochemistry can help tune overall conjugate structure and stability, supporting the preparation of defined, amino acid-derived conjugates for analytical and applied biochemical workflows.
5. Heterocycle And Diamine-Driven Synthesis
D-2,4-Diaminobutyric acid can serve as a chiral diamino acid precursor for heterocycle synthesis and nitrogen-rich scaffold generation in synthetic organic chemistry. The two primary amines and the carboxyl group enable multi-step cyclization strategies where protection of one amine and activation of the carboxyl group can direct ring formation and control chemoselectivity. The D-configured backbone provides a stereogenic element that can be carried into cyclic products, supporting the preparation of stereodefined nitrogen heterocycles relevant to peptidomimetics and molecular design. The resulting heterocyclic derivatives can function as intermediates for fine chemical synthesis and for building blocks used in structure-activity relationship studies.
6. Process Chemistry Intermediate For Industrial Synthesis
D-2,4-Diaminobutyric acid is relevant to process chemistry and specialty chemical production as a chiral amino acid intermediate that can be converted into protected amino acid derivatives and downstream nitrogen-functionalized products. The carboxylic acid and primary amines allow manufacturing routes that rely on protection/deprotection sequences and controlled activation steps to manage reactivity during scale-up. D-stereochemical integrity supports consistent product profiles when the diamino acid is incorporated into peptide-like intermediates, cationic linkers, or nitrogen-rich chemical libraries. The diamine functionality also enables conversion into industrially useful intermediates for polymer modification, functional material precursors, and other specialty chemical applications where defined amine density is required.
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