DL-2,3-Diaminopropionic acid hydrochloride is a free amino acid derivative classified as a diamino-substituted amino acid, featuring a three-carbon backbone bearing two primary amino groups at the 2- and 3-positions along with a carboxyl functional group. The molecule is provided as a hydrochloride salt, so the amino functionalities are present in protonated form under typical conditions, and the "DL" designation indicates a racemic mixture of stereoisomers at the stereogenic center. In research and peptide chemistry, this diamino acid is used as a building block for preparing polyamine-containing amino acid derivatives and for introducing additional amine handles into peptide or conjugate frameworks where orthogonal functionalization and subsequent derivatization may be required.
CAT No: CP05806
DL-2,3-Diaminopropionic acid hydrochloride is a hydrochloride salt of a diamino-substituted amino acid with the formula HOOC-CH2-CH(NH2)-CH2-NH2, providing both an α-amino group and an additional side-chain primary amine. The presence of two basic nitrogen functionalities enables salt formation and influences solubility, while the carboxylic acid supports standard amino acid coupling chemistry after appropriate activation. The DL stereochemical designation indicates a racemic mixture at the α-carbon, which affects stereocontrol in peptide assembly and makes the material suitable for workflows that tolerate or deliberately explore stereochemical variation. The diamine side chain can be selectively protected and later deprotected or functionalized, positioning the compound as a practical chiral-free amino acid building block and derivatization handle in peptide and synthetic intermediate chemistry.
1. Protected Diamino Building Blocks
DL-2,3-Diaminopropionic acid hydrochloride is used in protected amino acid synthesis where orthogonal protection of the α-amino and side-chain amine is required for sequential peptide coupling. The dual primary amines can be converted into N-protected derivatives while the carboxyl group is maintained for activation, enabling controlled formation of amide bonds during peptide building block preparation. The racemic stereochemistry can be retained for library-style synthesis or resolved downstream when a single stereoisomer is needed for stereodefined analogs. The resulting protected diamino amino acid intermediates support downstream peptide assembly and modular functional group installation on the side-chain nitrogen.
2. Peptide Coupling Chemistry
DL-2,3-Diaminopropionic acid hydrochloride is applied in peptide synthesis workflows that incorporate diamino functionality into peptide backbones or side-chain linkers. The carboxylic acid and α-amino group participate in standard amino acid coupling strategies after conversion to an activated acid equivalent, while the additional side-chain amine can be protected to prevent cross-reactivity during chain elongation. The hydrochloride salt form can be managed through base treatment to generate the free amine for coupling while maintaining compatibility with common peptide coupling reagents. Peptides containing this diamino motif can then be used as scaffolds for further derivatization, including post-assembly functionalization of the side-chain amine for conjugation or structure-activity relationship studies.
3. Chemical Biology Conjugation Handles
DL-2,3-Diaminopropionic acid hydrochloride serves as a source of diamino functionality for chemical biology applications that require amine-rich conjugation handles. The side-chain primary amine can be selectively functionalized to introduce reactive groups for bioconjugation chemistry, such as acylation, sulfonylation, or formation of amide-linked motifs that remain stable under typical assay conditions. The α-carboxyl group and amino functionality enable attachment strategies where the diamino unit acts as a flexible spacer within molecular probes or peptide-based tagging constructs. Racemic incorporation may be acceptable for probe development and comparative studies where stereochemical uniformity is not the primary variable.
4. Process Chemistry Intermediate
DL-2,3-Diaminopropionic acid hydrochloride is suitable for process chemistry intermediate preparation where a diamino amino acid can be routed into protected derivatives and downstream functional building blocks. The hydrochloride salt form provides a defined handling form for bulk synthesis and can be advantageous for consistent salt-based feedstock control prior to protection or activation steps. Orthogonal protection of the two amines supports manufacturing routes that minimize side reactions, enabling cleaner conversion to peptide-ready intermediates and reducing the need for extensive purification of competing amine-reactive species. The diamine side chain also supports conversion into specialty intermediates used in fine chemical synthesis, including linker units for polymer modification and amine-functional small molecules.
5. Synthetic Organic Derivatization
DL-2,3-Diaminopropionic acid hydrochloride is employed in synthetic organic chemistry as a multifunctional nitrogen-containing building block for derivatization into amine-rich intermediates. The combination of carboxylic acid and two primary amines enables formation of amide, urea, and sulfonamide derivatives after selective activation and protection/deprotection sequencing. The racemic nature allows exploration of stereochemical effects in downstream transformations, while the diamine motif can be used to generate constrained or branched nitrogen frameworks for heterocycle precursors. Downstream products can serve as intermediates for peptidomimetic construction, amine-functional materials, and other nitrogen-rich fine chemicals where controlled introduction of multiple amino sites is required.
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