H-D-Arg-OH*HCl

H-D-Arg-OH*HCl is the hydrochloride salt of the D-enantiomer of arginine, presenting a guanidinium-bearing side chain and a primary amino group with a carboxylic acid functionality. The D stereochemistry at the alpha carbon provides a chiral amino acid framework that can be used to probe stereochemical effects in peptide and protein contexts. Protonation of the guanidine moiety under acidic conditions yields strong ionic character and enables salt formation, while the free carboxyl group can be activated for coupling or converted into protected derivatives for peptide chemistry. As a chiral amino acid building block and biochemical research intermediate, the salt form supports controlled handling and downstream conversion into N- and C-terminally modified arginine derivatives.

1. Peptide Synthesis

H-D-Arg-OH*HCl is applied in peptide coupling workflows where the D-arginine residue serves as a stereochemically defined building block for D-amino acid incorporation. The guanidinium side chain and alpha-amino/carboxyl groups participate in standard peptide construction logic, with the guanidine often requiring orthogonal protection during iterative coupling to prevent side reactions. Hydrochloride salt formation can be leveraged during protection and activation steps to maintain solubility and reproducible reactivity of the amino acid. The resulting D-Arg-containing peptides can be used to generate peptide libraries, evaluate stereochemical determinants, and support synthesis of peptidomimetics with altered protease recognition.

2. Chemical Biology Probes

H-D-Arg-OH*HCl functions in chemical biology research as a chiral guanidinium-bearing amino acid for constructing probes that interrogate binding-site geometry and charge recognition. The strongly basic guanidinium group can be retained or selectively modified to tune electrostatic interactions, while the carboxyl group supports conjugation handles after activation. D stereochemistry at the backbone can be used to reduce susceptibility to proteolysis in labeling constructs, enabling longer-lived reagents for biochemical assays. Downstream derivatization can produce D-arginine-containing conjugates for receptor-binding studies, affinity reagents, and assay-compatible molecular scaffolds.

3. Bioconjugation Chemistry

H-D-Arg-OH*HCl is suitable for bioconjugation strategies that require a cationic side-chain motif for electrostatic association or for building defined linkers to biomolecules. The guanidinium functionality provides a persistent positive charge that can enhance interaction with anionic surfaces, nucleic acids, and certain protein microenvironments, while the alpha-carboxyl group enables formation of amide or ester linkages after activation. Hydrochloride salt handling supports reproducible salt-state behavior during coupling chemistry, which can matter for linker stability and solubility in aqueous media. The compound can be converted into protected or activated arginine derivatives that serve as intermediates for attaching peptides, tags, or functional moieties to proteins and other biomolecular targets.

4. Protected Amino Acid Intermediates

H-D-Arg-OH*HCl is commonly used as a starting chiral amino acid intermediate for preparing protected D-arginine derivatives compatible with automated or solution-phase peptide synthesis. The primary amino group and carboxylic acid can be selectively protected to control chemoselectivity during sequential coupling, while the guanidinium side chain can be managed through guanidine-protecting-group strategies to avoid undesired reactivity. D chirality is preserved through these protection and deprotection steps, enabling stereochemically defined downstream products for D-peptide and peptidomimetic construction. Resulting protected intermediates can be used to manufacture D-Arg-containing peptide building blocks, fragment libraries, and stereopure amino acid derivatives for fine chemical synthesis.

5. Process Chemistry Intermediate

H-D-Arg-OH*HCl serves as a chiral feedstock in process chemistry for manufacturing routes that require D-arginine as a stereochemically controlled intermediate. The salt form supports handling and can be integrated into industrial workflows for conversion into activated amino acid derivatives, protected building blocks, or derivatized intermediates used in peptide and specialty chemical production. The guanidinium group's strong basicity and ionic character guide choices for protection strategy, crystallization behavior, and downstream coupling compatibility. Industrial utilization can include preparation of stereodefined D-arginine-containing intermediates for peptide manufacturing, process-driven synthesis of functional amino acid derivatives, and supply of chiral building blocks for research-grade chemical production.

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