DL-2,4-Diaminobutyric acid is a non-proteinogenic, α-amino acid featuring a four-carbon backbone with two additional primary amino substituents at the 2- and 4-positions, classifying it as a diamino amino acid. The molecule contains both an amino group and a carboxyl functional group (as a free amino acid form) and is supplied as the DL stereochemical mixture, which reflects the presence of both stereoisomeric configurations at the chiral center. In research and peptide chemistry, it is used as a building block to introduce a polycationic side-chain motif into synthetic peptides and amino acid derivatives, and it can also serve as a substrate component for structure-activity studies and analytical method development involving amino acid derivatization and labeling.
CAT No: CP05303
DL-2,4-Diaminobutyric acid is a diamino acid with a four-carbon backbone bearing two primary amine functionalities at the 2- and 4-positions, enabling strong nucleophilicity and multiple sites for selective functionalization. The compound exists as a racemic mixture (DL), so it contains both stereochemical configurations at the chiral center when the 2-position is stereogenic, which affects stereochemical outcomes in downstream peptide and heterocycle assembly. The two amino groups can be orthogonally protected and later deprotected to control chemoselective peptide coupling, side-chain modification, and intramolecular transformations. As an amino acid-based intermediate, it participates in salt formation, protected amino acid synthesis, and scaffold construction where diamine spacing supports crosslinking, cyclization, and derivatization chemistry.
1. Peptide Synthesis
DL-2,4-Diaminobutyric acid is applied in peptide synthesis workflows that require a diamino side chain for building cationic or functionalized peptide analogs. The amino acid backbone and the additional side-chain amine provide two reactive handles that can be protected separately to enable controlled N- and side-chain coupling, followed by deprotection to reveal a free primary amine for subsequent conjugation. Racemic incorporation into peptide sequences can be used for generating stereochemically mixed libraries for structure-activity relationship studies, while selective protection strategies can still enforce chemoselectivity during coupling steps. Downstream, the resulting peptides or peptide fragments can be used as intermediates for further derivatization, including salt formation, linker attachment, and post-synthetic functionalization.
2. Amino Acid Derivatization
DL-2,4-Diaminobutyric acid is suitable for amino acid derivatization in synthetic organic chemistry where primary amines drive urea, amide, carbamate, and Schiff-base formation. The presence of two amino groups supports stepwise functionalization, allowing installation of orthogonal protecting groups or conversion into mono-derivatized intermediates that can later be transformed into peptide-compatible building blocks. The diamine spacing can facilitate intramolecular cyclization to form azacycles or to generate tethered linkers for materials and bioactive scaffold exploration. The compound's ability to form stable salts and protected derivatives also makes it useful for downstream intermediate preparation in fine chemical synthesis and for controlled handling during multi-step syntheses.
3. Heterocycle Construction
DL-2,4-Diaminobutyric acid is employed as a nitrogen-rich precursor for heterocycle synthesis, leveraging the two primary amines to enable ring closure and annulation strategies. The amino acid framework can be converted into protected intermediates that maintain a defined spatial arrangement of nucleophiles, supporting formation of azetidines, diazacycles, and other N-containing ring systems relevant to medicinal chemistry and chemical biology. Racemic stereochemistry can be carried through to generate mixed stereochemical outcomes in heterocycles when stereocontrol is not the primary objective, while protecting-group selection can still control which nitrogen participates first in cyclization. Resulting heterocyclic products can serve as scaffolds for SAR studies, fragment-based molecular design, and as intermediates for further functional group elaboration.
4. Bioconjugation Chemistry
DL-2,4-Diaminobutyric acid is applied in bioconjugation and chemical biology contexts where a diamine motif enables linker installation and amine-reactive coupling chemistry. The free primary amine functionality can be revealed after selective deprotection, then used for conjugation to activated carboxylates, activated carbonyls, or electrophilic linkers to generate stable amide or urea-containing connections. The amino acid-based structure can also be incorporated into peptide tags or adaptor fragments, where the additional amine provides a site for multivalent labeling or controlled crosslinking. Downstream, conjugates prepared from protected derivatives can be used to generate labeled biomolecule standards, affinity reagents, or functional probes for studying molecular recognition and biomolecular interactions.
5. Pharmaceutical Intermediate Preparation
DL-2,4-Diaminobutyric acid is used in pharmaceutical intermediate preparation where diamino acid motifs support synthesis of peptidomimetic fragments and nitrogen-rich building blocks. The compound's amino acid character allows conversion into protected amino acid derivatives that participate in peptide coupling chemistry, while the side-chain primary amine can be carried through as a protected functionality for later deprotection and derivatization. Racemic starting material can be leveraged for route development and library synthesis of analogs, with stereochemical resolution introduced downstream when a single configuration is required. Industrially relevant downstream utility includes preparation of chiral or achiral intermediates for fine chemical manufacturing, including linker-bearing scaffolds and protected diamine-containing units used in multi-step synthesis toward complex nitrogenous molecules.
6. Process Chemistry Intermediate
DL-2,4-Diaminobutyric acid is suitable for process chemistry intermediate applications that benefit from robust amine reactivity and straightforward conversion into protected derivatives. The two primary amines can be selectively masked to manage chemoselectivity, enabling manufacturing routes that separate protection, coupling, and deprotection stages without losing the diamine functionality needed for later transformations. The racemic nature supports simpler upstream sourcing and can reduce constraints in early-stage intermediate production, while protecting-group strategies can still control which nitrogen is available for subsequent steps. Downstream, protected amino acid derivatives derived from DL-2,4-Diaminobutyric acid can be employed in specialty chemical production and industrial fine chemical synthesis where controlled functional group presentation is required for consistent peptide-building-block preparation and subsequent functionalization.
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5. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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