L-2,4-Diaminobutyric acid is a proteinogenic amino acid analogue featuring a four-carbon backbone bearing two amino substituents at the 2- and 4-positions, classifying it as a diamino amino acid with a primary amino group and an additional amino-bearing side chain. The molecule contains a free carboxyl functional group and two basic amino functionalities that can participate in acid-base equilibria, with stereochemistry consistent with the "L-" designation at the 2-position. In peptide and amino acid derivative synthesis, it functions as a building block for incorporating a diamino side chain into peptides or for preparing structure-activity and chemical biology probes that require additional amine functionality for conjugation, crosslinking, or analytical derivatization.
CAT No: CP05302
CAS No:1883-09-6
Synonyms/Alias:1883-09-6;(S)-2,4-Diaminobutanoicaciddihydrochloride;L-2,4-Diaminobutyricaciddihydrochloride;(S)-(+)-2,4-Diaminobutyricaciddihydrochloride;SBB003640;2,4-diaminobutyricaciddihydrochloride;H-Dab-OH?HCl;(S)-(+)-2,4-Diamino-n-butyricAcidDihydrochloride;(2S)-2,4-diaminobutanoicacid,chloride,chloride;C4H10N2O2.2HCl;(2S)-2,4-diaminobutanoicaciddihydrochloride;MFCD00064561;D-Dab.2HCl;AC1MC4K8;KSC911A8D;D8376_SIGMA;SCHEMBL318746;32830_FLUKA;CTK8B1081;L-2,4-Diaminobutyricaicd2HCl;MolPort-001-766-373;ANW-23392;CH-296;FD1067;AC-5662
L-2,4-Diaminobutyric acid is an L-configured, non-proteinogenic 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 presence of two amines with different spatial accessibility enables selective derivatization strategies that can tune basicity, solubility, and coupling behavior during protected amino acid synthesis. The stereogenic center at C2 (L-configuration) supports stereochemically defined incorporation into peptide-like scaffolds, while the free carboxyl group can be activated for amide bond formation or converted into amino acid ester intermediates. The bifunctional amine pattern makes the compound suitable for downstream transformations such as orthogonal protection, nucleophilic substitution, and formation of urea/amide or heterocycle-forming intermediates used in synthetic and biochemical workflows.
1. Peptide Synthesis
L-2,4-Diaminobutyric acid serves as a peptide building block for constructing diamino-substituted peptide segments and peptidomimetic backbones in research-grade peptide synthesis. The carboxylic acid enables C-terminal activation for amide coupling, while the two primary amines can be selectively protected to control which nitrogen participates in side-chain functionalization versus backbone coupling. Orthogonal N-protection strategies can be applied to manage stepwise peptide assembly, including selective deprotection to reveal a targeted side-chain amine for subsequent conjugation or crosslinking. The resulting diamino-containing peptides and analogs can be used to probe sequence-dependent properties, binding motifs, and scaffold stability in peptide science and chemical biology.
2. Amino Acid Derivatization
L-2,4-Diaminobutyric acid is well matched to amino acid derivatization workflows that require controlled functional group interconversion of primary amines and the carboxyl group. The dual amino functionality supports selective formation of mono-protected derivatives, enabling downstream conversion into amides, ureas, sulfonamides, or carbamates while preserving a defined reactive handle for further chemistry. The carboxyl group can be transformed into activated esters or amide-forming intermediates, facilitating incorporation into larger molecules for fine chemical synthesis and process chemistry intermediate preparation. Diamino-functional derivatives generated from L-2,4-diaminobutyric acid can be used to build nitrogen-rich fragments for medicinal chemistry, polymerizable monomers, or labeled reagents used in analytical and synthetic applications.
3. Chemical Biology Conjugation
L-2,4-Diaminobutyric acid can be employed in chemical biology for biomolecule labeling and conjugation strategies that rely on amine-reactive coupling chemistry. The side-chain primary amines provide nucleophilic sites for formation of stable linkages such as amide or urea bonds with electrophilic partners, enabling attachment to carrier proteins, peptides, or affinity tags. The L-stereocenter can be retained in conjugated constructs to maintain stereochemically defined recognition features when the amino acid is incorporated into peptide-based probes. Conjugation products derived from L-2,4-Diaminobutyric acid may serve as tools for studying molecular interactions, tracking biomolecular localization, or generating structured chemical probes for biochemical research.
4. Peptidomimetics And SAR Studies
L-2,4-Diaminobutyric acid supports peptidomimetic construction for structure-activity relationship studies where nitrogen-rich side chains modulate binding and physicochemical behavior. The diamino substitution pattern can be used to tune hydrogen-bonding capacity, basicity, and metal coordination potential within a scaffold, while the carboxyl-derived linkage position enables incorporation into constrained analogs. Selective protection and deprotection of the two amines allow stepwise diversification of the side chain, supporting analog libraries that vary charge distribution and functional group identity. Peptidomimetic derivatives prepared from this amino acid can be applied to SAR investigations, fragment elaboration, and molecular design efforts in drug discovery and chemical biology.
5. Pharmaceutical Manufacturing Intermediates
L-2,4-Diaminobutyric acid is suitable for pharmaceutical manufacturing intermediate preparation where diamino-functional building blocks are required for downstream synthesis of active pharmaceutical ingredient (API) scaffolds or process intermediates. The amino acid framework provides a controllable platform for converting the carboxyl group into coupling-ready derivatives and for managing nitrogen reactivity through protection-group selection compatible with multi-step routes. The L-configuration supports stereochemically defined intermediates when stereochemical integrity must be maintained through intermediate stages. Diamino-containing intermediates derived from L-2,4-Diaminobutyric acid can feed into heterocycle-forming sequences, amide/urea formation steps, and other nitrogen incorporation operations used in specialty chemical production and industrial chemical manufacturing.
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3. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
4. Urinary Metabolites Associated with Blood Pressure on a Low-or High-Sodium Die
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