H-D-Arg-NH2*2HCl is a D-configured amino acid derivative of arginine in which the carboxyl group is replaced by a primary amide (argininamide) while retaining the guanidinium-containing side chain characteristic of arginine analogues. The molecule bears an alpha-amino group and an alpha-carboxamide functionality, and the guanidinium side chain is present as a protonated, salt-associated species under the stated dihydrochloride form, with the D stereochemistry indicated by the "H-D" prefix. As a free, salt-form amino acid derivative with a basic guanidinium handle and an amide terminus, it is used as a substrate analog and building block for peptide and peptidomimetic synthesis as well as for chemical biology and analytical studies that require a protected-free, positively charged arginine-like motif.
CAT No: CP25578
CAS No:203308-91-2
Chemical Name:D-Arginine amide dihydrochloride
H-D-Arg-NH2*2HCl is a D-configured arginine amino acid derivative presented as a dihydrochloride salt, featuring a guanidinium side chain that is strongly basic and protonated under typical coupling and storage conditions. The molecule contains a primary amino group at the alpha position and a terminal amino functionality (as the free amino acid amine form), enabling straightforward conversion into peptide-grade intermediates through standard amino group protection and carboxyl activation strategies. The D stereochemistry at the alpha carbon supports stereochemically controlled incorporation into peptide analogs, where resistance to proteolysis and altered receptor recognition may be engineered through chirality. The salt form improves handling and solubility while also influencing salt-dependent reactivity during coupling, deprotection, and downstream derivatization of the guanidinium functionality.
1. Peptide Synthesis
H-D-Arg-NH2*2HCl is applied in peptide building workflows where a D-arginine residue is required for stereodefined peptide coupling and peptidomimetic construction. The guanidinium side chain provides a cationic interaction handle that can be selectively protected (for example, via guanidinium-protecting groups) to enable chemoselective amide bond formation at the alpha-amino functionality. The alpha-amino and terminal amine features support conversion into N-protected D-arginine derivatives compatible with Fmoc/Boc or other orthogonal protection schemes, facilitating stepwise solid-phase or solution-phase peptide assembly. The resulting D-arginine-containing peptides and analogs can be used to probe sequence-dependent binding modes and to generate protease-resistant peptide frameworks for biochemical research and industrial fine chemical synthesis.
2. Chemical Biology Probes
H-D-Arg-NH2*2HCl serves as a chiral, cationic amino acid component for chemical biology studies that require controlled guanidinium-mediated recognition. The strongly basic guanidinium group can be leveraged for electrostatic and hydrogen-bonding interactions in labeling reagents, affinity probes, and receptor-binding peptide fragments. The D stereochemistry enables construction of stereochemically distinct probes that can be incorporated into larger conjugates while maintaining the arginine side-chain charge distribution. Downstream derivatization can include attachment of linkers or reporter groups to the amino termini after appropriate protection/deprotection cycles, supporting generation of biomolecule-binding tools and mechanistic probes used in applied research and specialty chemical production.
3. Peptidomimetics And SAR
H-D-Arg-NH2*2HCl is suitable for peptidomimetic and structure-activity relationship studies where incorporation of a D-arginine stereocenter tunes binding and stability. The guanidinium side chain provides a persistent positive charge that can be retained in analogs while the backbone stereochemistry is varied through D-amino acid substitution. The terminal amino functionality enables conversion into protected intermediates for iterative scaffold diversification, including formation of amide-linked analogs, cyclization precursors, or side-chain modified derivatives. The resulting D-arginine-containing libraries can be applied to SAR mapping of charge and stereochemical effects in molecular design programs and combinatorial fine chemical synthesis.
4. Protected Amino Acid Chemistry
H-D-Arg-NH2*2HCl is used as a chiral starting material in protected amino acid synthesis and amino acid intermediate preparation for peptide-grade manufacturing routes. The dihydrochloride salt form and the presence of both alpha and terminal amine groups allow controlled selection of protection strategies, including orthogonal N-protection for selective coupling and guanidinium protection for preventing side reactions during activation of neighboring functional groups. D stereochemistry is maintained through protection, activation, and deprotection steps, supporting stereochemical integrity in downstream peptide building block preparation. The compound can be transformed into N-protected D-arginine derivatives and activated forms that feed into process chemistry workflows for producing stereodefined peptide intermediates and specialty chemical reagents.
5. Bioconjugation Chemistry
H-D-Arg-NH2*2HCl supports bioconjugation and biomolecule modification strategies where a cationic D-arginine motif is used to influence conjugate solubility, binding, and linker positioning. The guanidinium group can be used as a functional recognition element in conjugates, while the amino functionalities enable formation of amide or urea linkages after conversion to appropriately protected or activated derivatives. The D configuration can help modulate conjugate stability against enzymatic degradation, which is relevant for preparing longer-lived labeling reagents and analytical standards. The resulting conjugation-ready intermediates can be incorporated into larger constructs such as peptide-tagged biomolecule probes, affinity handles, and research-grade labeling materials used across biochemical research and industrial analytical reagent development.
6. Analytical Research Standards
H-D-Arg-NH2*2HCl can be employed in analytical research as a stereochemically defined amino acid reference for method development and characterization of peptide and protein hydrolysates. The D-arginine stereocenter and guanidinium side chain provide a distinct mass and retention behavior that can assist in chromatographic or mass spectrometric discrimination between L- and D-arginine-containing materials. Salt-state behavior and the presence of multiple protonation sites make the compound useful for calibrating ionization and for evaluating derivatization or detection strategies targeting basic amino acid residues. The compound's role as a defined chiral building block supports downstream preparation of labeled or derivatized standards for peptide analytics, QA/QC-oriented intermediate checks, and specialty analytical standard production in industrial chemistry settings.
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