(5R,2S)-2,5-Diaminoadipic acid 2HCl is a diamino dicarboxylic amino acid derivative featuring a six-carbon backbone with amino groups at the 2- and 5-positions and carboxyl functional groups at both ends, with stereochemistry specified as (5R,2S). The molecule is present as a dihydrochloride salt, so its amino functionalities are protonated as chloride counterions, which affects solubility and provides distinct sites for chemoselective derivatization during peptide-related synthesis. In research contexts, this salt form is used as a defined building block or precursor for preparing modified amino acid and peptide frameworks, including incorporation of a diaminoadipic motif for linker design, crosslinker construction, and analytical standards where controlled functional-group placement is required.
CAT No: CP05104
CAS No:213686-09-0
Synonyms/Alias:(2R,5S)-2,5-Diaminohexanedioicaciddihydrochloride;213686-09-0;AKOS015911730;AK-34085;FT-0647501;(5R,2S)-2,5-Diaminoadipicaciddihydrochloride;I14-37360
(5R,2S)-2,5-Diaminoadipic acid 2HCl is a diamino dicarboxylic amino acid salt provided as a dihydrochloride, featuring two stereogenic centers and two primary amino groups that can be used for selective derivatization and downstream coupling chemistry. Its salt form improves handling and reproducibility for synthetic and analytical workflows where well-defined, water-compatible reagents are required. The combination of a rigid, stereodefined backbone and multiple amine functionalities makes it a practical building block for preparing substituted amino acid derivatives and for constructing nitrogen-rich motifs in peptide and peptidomimetic research.
1. Peptidomimetic Building Blocks
(5R,2S)-2,5-Diaminoadipic acid 2HCl is used as a nitrogen-rich amino acid building block for peptidomimetic and modified peptide construction, where incorporation of a diaminoadipic framework helps introduce additional amine functionality for further functionalization. Researchers in medicinal chemistry and chemical biology often employ this stereodefined diamino acid to generate side-chain substituted analogs, to tune physicochemical properties through controlled derivatization, and to create scaffolds that can be diversified into libraries of amine-bearing compounds. The dihydrochloride salt form supports consistent reagent dosing in coupling and derivatization steps, which is particularly valuable in parallel synthesis and SAR workflows.
2. Pharmaceutical Intermediate Synthesis
(5R,2S)-2,5-Diaminoadipic acid 2HCl serves as a practical intermediate for the preparation of substituted diaminoadipic derivatives used in pharmaceutical intermediate development. Process and R&D chemists value the presence of two primary amines and the stereodefined backbone as handles for selective protection/deprotection strategies and for building multiamine fragments that appear in kinase inhibitor, protease inhibitor, and other medicinal chemistry chemotypes. As a dihydrochloride, it is commonly selected when robust, weighable salt forms are preferred for scale-up planning and when downstream conversion to protected or activated derivatives is required to access advanced intermediates.
3. Amine-Functionalized Derivative Preparation
(5R,2S)-2,5-Diaminoadipic acid 2HCl is widely used to generate amine-functionalized derivatives for chemical biology tools and materials-oriented chemistry, leveraging its two primary amino groups for stepwise or orthogonal derivatization strategies. Teams developing labeled or tagged scaffolds often start from this diamino acid to introduce additional reactive groups, linkers, or solubilizing substituents while maintaining stereochemical integrity. The salt form supports reproducible handling and helps maintain consistent reactivity during derivatization, which is useful for workflows that require multiple functional-group transformations from a single, well-defined starting material.
4. Analytical Reference Material Development
(5R,2S)-2,5-Diaminoadipic acid 2HCl is used in analytical method development and reference preparation where a defined stereochemical diaminoadipic standard is needed to support identification and quantification of related amino acid derivatives. Analytical chemistry groups preparing LC methods, derivatization protocols, or impurity panels often select this salt form to improve consistency across runs and to ensure the reference material matches the chemical form used in sample preparation. Its well-defined structure and dihydrochloride composition make it a useful anchor compound when validating workflows that monitor amine-containing intermediates and amino acid derivative profiles.
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