Boc-D-Homoarginine hydrochloride is a protected, non-proteinogenic amino acid derivative in which a D-configured homoarginine skeleton is capped with a tert-butoxycarbonyl (Boc) protecting group on the α-amino functionality and provided as a hydrochloride salt. The side chain contains a guanidinium group characteristic of arginine-like functionality, enabling strong hydrogen-bonding and ionic interactions, while the molecule also bears a free carboxylic acid suitable for coupling chemistry. As a Boc-protected amino acid hydrochloride, it functions as a stepwise building block for peptide synthesis workflows and as a precursor for preparing guanidinium-containing amino acid and peptide analogues used in structure-activity studies, chemical biology labeling, and related analytical method development.
CAT No: CP06106
Boc-D-Homoarginine hydrochloride is a D-configured, protected homoarginine derivative bearing a Boc-protected alpha-amino group and a side-chain guanidinium functionality characteristic of arginine-like amino acids. As the hydrochloride salt, it is supplied in a form commonly used to control handling and reactivity during peptide assembly and intermediate synthesis. This reagent is widely selected in workflows that require a stereochemically defined, guanidinium-containing amino acid building block for incorporation into modified peptides or for preparing downstream protected intermediates.
1. Stereodefined Peptide Building Block
Boc-D-Homoarginine hydrochloride is used by peptide chemists to introduce a D-stereocenter and an arginine-mimetic side chain into peptide sequences where stereochemical control is critical. The Boc protection on the alpha-amino group supports its role as a protected amino acid building block for stepwise peptide assembly, while the guanidinium side chain enables formation of salt bridges and strong electrostatic interactions in the resulting peptide. Researchers developing stereochemically constrained peptides, protease-resistant analogs, or structure-function probes often choose this specific D-protected homoarginine form to tune backbone stereochemistry and side-chain charge presentation without relying on post-assembly guanidinium installation.
2. Guanidinium-Containing Intermediate Synthesis
Boc-D-Homoarginine hydrochloride serves as a practical starting material for preparing guanidinium-bearing pharmaceutical intermediates and specialty amino acid derivatives used in medicinal chemistry programs. The combination of Boc protection and the guanidinium functionality allows downstream transformations that require a stable, isolable amino acid core while preserving the strongly basic side chain for later coupling, functional group interconversion, or salt formation. Process and custom synthesis teams commonly select this reagent when a stereodefined homoarginine unit is needed as a building block for analog libraries, peptidomimetic scaffolds, or charged linker motifs where the guanidinium group is retained through multiple synthetic steps.
3. Modified Peptide and Peptidomimetic Design
Boc-D-Homoarginine hydrochloride is frequently incorporated into modified peptides and peptidomimetic constructs to emulate arginine-like binding interactions with a defined stereochemical outcome. The D-configuration at the alpha position supports the design of non-natural peptide architectures used in chemical biology and structure-activity relationship studies, where altered stereochemistry can change conformational preferences and interaction patterns. In these workflows, the protected alpha-amino group streamlines sequential coupling strategies, and the guanidinium side chain provides a persistent, protonatable functionality that is valuable for electrostatic recognition motifs and for maintaining charge localization in the final peptide or peptidomimetic scaffold.
4. Charged Linker Development
Boc-D-Homoarginine hydrochloride is also applied in the synthesis of charged peptide linkers and amino acid-based fragments used to control solubility, binding-like electrostatics, and macromolecular association in research materials. The guanidinium side chain offers a robust cationic handle that can be carried into conjugates, multicomponent assemblies, or functional fragments where strong ionic interactions are desired. By using this protected, stereodefined homoarginine salt as the building block, materials and chemical biology developers can incorporate a consistent arginine-like motif into larger constructs while maintaining synthetic compatibility through the Boc-protected alpha-amino group during fragment assembly.
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