L-2,3-Diaminopropionic acid hydrochloride is a free amino acid derivative classified as a diamino acid, featuring a three-carbon backbone bearing two primary amino substituents at the 2- and 3-positions along with a carboxylic acid group. The molecule is present as a hydrochloride salt, which protonates the amino groups to form a chloride counterion, and the "L" designation indicates the stereochemical form at the chiral center within the 2,3-diaminopropionic acid framework. In peptide and amide synthesis workflows, the two amino functionalities provide orthogonal sites for stepwise functionalization or incorporation into protected peptide building blocks, while the salt form supports aqueous handling for preparing amino acid solutions used in labeling, conjugation, and analytical derivatization.
CAT No: CP05805
CAS No:1482-97-9
Synonyms/Alias:1482-97-9;(S)-2,3-diaminopropanoicacidhydrochloride;3-Amino-L-alaninehydrochloride;L-2,3-Diaminopropionicacidhydrochloride;H-Dapa-OH.HCl;L(+)-2,3-Diaminopropionicacidhydrochloride;(S)-(+)-2,3-DiaminopropionicAcidHydrochloride;L-3-AminoalanineHydrochloride;SBB053581;UNII-68H9573890;L(+)-2,3-DiaminopropionicacidHCl;L-DapCL;(2S)-2,3-diaminopropanoicacidhydrochloride;D-(-)-2,3-Diaminopropionicacidhydrochloride;H-DL-Dap-OH.HCl;D5414_SIGMA;SCHEMBL5548567;3-AMINO-L-ALANINE2HCL;CTK0I4999;MolPort-003-930-261;SKWCZPYWFRTSDD-DKWTVANSSA-N;EBD13095;L-Alanine,3-amino-,hydrochloride;ANW-21128;CD-710
L-2,3-Diaminopropionic acid hydrochloride is a chiral amino acid derivative bearing a vicinal diamine motif on the 2,3-positions of the propionic acid backbone, delivered as a hydrochloride salt to ensure protonated, water-compatible handling. The molecule contains a carboxylic acid functionality alongside two primary amines with defined stereochemistry at the carbon bearing the amino substituents, enabling controlled chemoselective transformations. The salt form modulates solubility and can influence coupling behavior, while the diamine array supports orthogonal protection strategies to direct sequential peptide bond formation or side-chain derivatization. The resulting reactivity profile makes it a practical intermediate for constructing amino-rich motifs, including diamino-substituted peptide segments and chiral scaffolds used in biochemical and process chemistry.
1. Peptide Synthesis
L-2,3-Diaminopropionic acid hydrochloride is applied in peptide synthesis workflows where a diamino-substituted amino acid building block is required for incorporating amino-rich sequences. The carboxylic acid and the stereogenic amino-bearing carbon support standard amino acid coupling chemistry, while the two primary amines on the side positions can be protected selectively to prevent undesired crosslinking during N-to-C peptide bond formation. Hydrochloride salt handling can be advantageous for aqueous or biphasic preparation steps, provided that base-mediated deprotonation is managed during activation and coupling. Protected derivatives derived from this scaffold can be used to generate peptide segments that carry defined cationic character for downstream conjugation, affinity studies, or biomolecular recognition investigations. The diamine functionality also supports subsequent deprotection and functionalization to access peptide analogs with tailored charge density.
2. Chemical Biology
L-2,3-Diaminopropionic acid hydrochloride serves chemical biology programs aiming to probe molecular recognition using amino-rich, charge-defined constructs. The vicinal diamine functionality can be converted into protected forms for incorporation into peptides, peptidomimetics, or linker regions that participate in electrostatic interactions and hydrogen-bonding networks. The stereochemical integrity of the L-configuration supports consistent spatial presentation of the two amino groups, which can be important for structure-activity relationship studies of binding motifs and receptor-interacting sequences. Deprotection and controlled derivatization enable access to conjugation handles for labeling, crosslinking, or affinity reagent generation. The compound's amino acid backbone further aligns with established synthetic logic for building chiral, functionalized biomolecule probes.
3. Bioconjugation Chemistry
L-2,3-Diaminopropionic acid hydrochloride is suitable for bioconjugation chemistry where diamine-containing linkers provide reactive sites for coupling to biomolecules. The two primary amines can be orthogonally protected to enable sequential introduction of functional groups such as acylating moieties, carbamate-forming groups, or activated ester-compatible intermediates after deprotonation. The carboxylic acid enables transformation into activated derivatives that can be used to position the diamine-bearing stereocenter within conjugates, including peptide-tagged or polymer-tethered systems. Hydrochloride salt form supports handling during salt-to-base transitions, which can be relevant for reproducible derivatization under controlled pH conditions. Downstream products can function as intermediates for constructing cationic conjugates used in analytical assays, biomolecule labeling, and targeted probe assembly.
4. Chiral Building Block Synthesis
L-2,3-Diaminopropionic acid hydrochloride is employed as a chiral amino acid intermediate for stereoselective synthesis of diamino-substituted scaffolds and amino-rich fragments. The L-stereochemistry at the 2,3-diaminopropionic framework provides a defined three-dimensional arrangement that can be retained through protection, activation, and coupling steps to generate enantiopure intermediates. The presence of two primary amines supports orthogonal protection-group strategies, enabling selective functionalization at one nitrogen while preserving the other for subsequent transformations. The carboxylic acid can be converted into peptide-coupling-ready forms or into protected ester/amide derivatives as part of a controlled synthetic route. Such chiral intermediates can be used to access unnatural amino acid analogs, peptidomimetic cores, and process chemistry intermediates where stereochemical fidelity is required.
5. Pharmaceutical Intermediate Preparation
L-2,3-Diaminopropionic acid hydrochloride is relevant to pharmaceutical intermediate preparation programs that require amino-functional, chiral building blocks for medicinal chemistry and process development. The amino acid backbone, combined with a vicinal diamine side functionality, enables incorporation into peptide-like structures and into linker fragments that can be further modified to tune polarity, basicity, and hydrogen-bonding patterns. Protection of the amines and activation of the carboxylic acid can support downstream synthesis of amide-linked intermediates, heteroatom-rich fragments, or protected amino acid derivatives used in stepwise assembly of larger molecules. Hydrochloride salt formation can assist in controlled handling and consistent salt-state conversion during manufacturing-oriented workflows. The compound thereby functions as an amino-rich chiral intermediate compatible with iterative synthetic methodology for fine chemical production and scale-up planning.
1. Cell-based adhesion assays for isolation of snake venom’s integrin antagonists
3. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis
5. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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