(5R,2R)-2,5-Diaminoadipic acid 2HCl is a diamino dicarboxylic amino acid derivative classified as an aliphatic amino acid building block, featuring a six-carbon chain with amino substituents at the 2- and 5-positions and carboxylic acid functionality at the 1- and 6-positions, with stereochemistry specified as (5R,2R). The molecule is present as a dihydrochloride salt, so its basic amino groups are protonated as chloride salts, which influences solubility and chemoselectivity during handling and coupling chemistry. In peptide and peptidomimetic synthesis and in chemical biology workflows that require a protected or salt-stabilized diamino-dicarboxylic scaffold, it serves as a precursor for introducing a bifunctional side-chain motif that can be further transformed into more complex amino acid derivatives for structure-activity studies, labeling, or conjugation.
CAT No: CP05103
CAS No:213686-08-9
Synonyms/Alias:213686-08-9;(5R,2R)-2,5-Diaminoadipicaciddihydrochloride
(5R,2R)-2,5-Diaminoadipic acid 2HCl is a chiral diamino dicarboxylic acid salt supplied as the dihydrochloride, providing two amino groups for subsequent derivatization and two carboxyl groups that support conversion into protected intermediates or activated building blocks. Its defined (5R,2R) stereochemistry and salt form make it a practical precursor for stereochemically controlled synthesis and for downstream coupling chemistry where free amines and carboxylates must be managed selectively.
1. Chiral Diaminocarboxylic Intermediate
(5R,2R)-2,5-Diaminoadipic acid 2HCl is used as a stereodefined intermediate in the preparation of chiral diamino dicarboxylic acid derivatives for medicinal chemistry and peptidomimetic research. Researchers and process chemists rely on the presence of two amino functionalities to access selectively protected mono- and bis-derivatives, while the two carboxyl groups enable formation of activated esters/amides or further functional group interconversions. The dihydrochloride salt form improves handling and reproducible dosing in synthesis planning, particularly when downstream steps require controlled amine availability and consistent salt stoichiometry.
2. Peptide Building Block Development
(5R,2R)-2,5-Diaminoadipic acid 2HCl serves as a building block for the synthesis of constrained peptides and peptidomimetic scaffolds that incorporate a stereodefined diaminoadipic motif. Peptide chemistry groups use this reagent when they need a diamino dicarboxylic unit that can be incorporated into longer sequences after appropriate protection and coupling strategy selection. The two amines allow design flexibility for side-chain functionalization or for generating orthogonally protected variants used in segment assembly and modified-peptide construction, supporting workflows used in custom peptide synthesis and structure-activity relationship studies.
3. Pharmaceutical Intermediate Synthesis
(5R,2R)-2,5-Diaminoadipic acid 2HCl is commonly employed in pharmaceutical intermediate development where a chiral, diamino dicarboxylic acid framework is required for late-stage derivatization. Process development teams use it to generate downstream intermediates such as amide/ester derivatives and protected diamines that feed into larger synthetic sequences for small-molecule and peptide-like candidates. The salt form and defined stereochemistry help maintain batch-to-batch consistency for multi-step manufacturing planning, especially when downstream transformations depend on accurate stoichiometry and controlled functional group reactivity.
4. Analytical Reference Derivatization
(5R,2R)-2,5-Diaminoadipic acid 2HCl is also used in analytical method development and reference material preparation through derivatization workflows that require a known chiral diamino dicarboxylic acid. Analytical chemistry laboratories use it to prepare standards or calibration supports for chiral separation and amino-acid related quantification strategies, where the defined (5R,2R) configuration and availability of two amines enable derivatization chemistry that improves detectability. The dihydrochloride salt form facilitates reproducible preparation of derivatized standards and helps ensure consistent starting material composition for method qualification and routine analytical runs.
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