D-2,4-Diaminobutyric acid dihydrochloride

D-2,4-Diaminobutyric acid dihydrochloride is a D-configured amino acid derivative featuring a four-carbon backbone with two amino substituents at the 2- and 4-positions, supplied as the dihydrochloride salt to maintain high aqueous compatibility. The molecule contains two primary amines that can be selectively protected or chemoselectively functionalized, enabling controlled reactivity during peptide coupling, side-chain elaboration, and downstream derivatization. The stereogenic center at C-2 provides defined chiral information for asymmetric synthesis planning and for producing stereochemically consistent peptide or peptidomimetic analogs. Salt formation with hydrochloride influences salt-handling and coupling conditions by moderating basicity and improving solubility, while leaving the underlying diamino functionality available for protected-amino-acid strategies.

1. Peptide Synthesis

D-2,4-Diaminobutyric acid dihydrochloride supports peptide building workflows where a chiral diamino acid residue is incorporated to introduce side-chain amine functionality into peptide frameworks. The protected amino group at the α-position can be engaged in amide bond formation, while the additional side-chain primary amine can be masked with an orthogonal protecting group to control coupling order and minimize side reactions. D-configuration at the α-carbon enables stereodefined incorporation into peptide analogs used for peptide structure studies and chemically defined sequence construction. Salt-state handling can be integrated into synthesis planning for aqueous-compatible steps, with deprotection enabling access to the free side-chain amine for subsequent functionalization.

2. Side-Chain Functionalization

D-2,4-Diaminobutyric acid dihydrochloride is suitable for side-chain modification chemistry because it presents two primary amines that can be transformed into a range of reactive or conjugation-ready motifs. Orthogonal protection of one amine while functionalizing the other enables targeted derivatization such as acylation, sulfonylation, carbamate formation, or formation of urea/amide linkages for controlled electronic and steric tuning. The D-stereocenter helps maintain stereochemical integrity when the diamino acid is used as a chiral intermediate for generating stereodefined functionalized amino acid derivatives. Downstream products from these transformations can serve as handles for crosslinking, affinity-tag attachment, or incorporation into peptidomimetic scaffolds used in chemical biology and applied synthetic chemistry.

3. Chemical Biology Probes

D-2,4-Diaminobutyric acid dihydrochloride can be applied in chemical biology research to generate amino acid-derived probes that rely on amine-based conjugation and defined stereochemistry. The presence of a protected/derivatizable side-chain primary amine supports attachment to electrophiles such as activated esters, isothiocyanates, aldehydes, or carboxylate-activated coupling partners, enabling controlled labeling of peptides, linkers, or biomolecule-modifying reagents. D-configuration at the α-carbon can be leveraged when stereochemical fidelity is required for binding-site mimicry in peptide-based molecular recognition studies. The dihydrochloride form facilitates practical handling in aqueous or mixed-solvent conjugation workflows after appropriate protection-state management.

4. Bioconjugation Chemistry

D-2,4-Diaminobutyric acid dihydrochloride is relevant to bioconjugation strategies where diamino functionality provides multiple orthogonal attachment points for constructing multivalent conjugates. The α-amino and side-chain amino groups can be differentially protected to enable sequential coupling, supporting the design of linkers for attaching peptides, polymers, or biomolecular targeting units with controlled spacing and charge distribution. Salt formation with hydrochloride can improve solubility for intermediate preparation, while later deprotection and neutralization can restore nucleophilicity for conjugation steps. Resulting conjugation-ready intermediates can be used to build defined bioconjugates for analytical assays, reagent development, and structure-guided molecular design in applied biochemical research.

5. Process Chemistry Intermediate

D-2,4-Diaminobutyric acid dihydrochloride functions as a chiral amino acid intermediate for process chemistry and fine chemical synthesis where robust diamine reactivity and stereochemical control are required. The two primary amines enable a protecting-group strategy that can be adapted to manufacturing routes, including selective masking for predictable coupling behavior and controlled deprotection to access the free side-chain amine at a defined stage. D-stereochemistry supports consistent feedstock specification for producing stereodefined peptide building blocks and peptidomimetic fragments used across downstream synthetic programs. Industrial utility emerges from its role in preparing functionalized amino acid derivatives that can be scaled as intermediates for specialty chemical production and chemically defined reagent manufacture.

1. Genetic, cellular, and structural characterization of the membrane potential-dependent cell-penetrating peptide translocation pore

2. Implications of ligand-receptor binding kinetics on GLP-1R signalling

3. Sex differences in oxidative stress level and antioxidative enzymes expression and activity in obese pre-diabetic elderly rats treated with metformin or liraglutide

4. Myotropic activity of allatostatins in tenebrionid beetles

5. The effect of B-type allatostatin neuropeptides on crosstalk between the insect immune response and cold tolerance