D-Homoarginine hydrochloride is a D-configured, non-proteinogenic amino acid derivative in the arginine family, featuring an extended side chain relative to arginine (homo-arginine) that terminates in a guanidinium functionality. The molecule contains a free amino group and a carboxyl group, with the guanidinium side chain providing strong cationic character under typical conditions, while hydrochloride formation indicates protonation and chloride counterion association. It is used as a defined amino acid building block and analytical standard for peptide and amino acid studies, including structure-activity and labeling workflows where the D-homoarginine scaffold and guanidinium-bearing side chain are required.
CAT No: CP06104
D-Homoarginine hydrochloride is a D-configured, non-proteinogenic amino acid derivative featuring an extended guanidinium-bearing side chain that mimics the charge distribution of arginine while increasing the carbon count between the α-carbon and the terminal basic functionality. The hydrochloride salt form provides a defined protonation state for the side-chain guanidine and the amino group, which influences solubility, salt-handling in synthesis, and compatibility with aqueous or mixed-solvent coupling conditions. The molecule contains a free α-carboxyl group and a strongly basic guanidinium moiety that can participate in salt formation, ion-pairing, and selective protection strategies during amino acid derivatization. As a chiral amino acid intermediate, D-homoarginine hydrochloride can be incorporated into peptide-like structures or converted into protected derivatives for downstream stereocontrolled synthesis and biochemical research workflows.
1. Peptide Synthesis
D-Homoarginine hydrochloride is applied in peptide synthesis and peptide building block preparation where the D-stereocenter and guanidinium side chain enable incorporation of a charged, arginine-mimetic residue into linear peptides and peptidomimetic scaffolds. The α-carboxyl and α-amino functionality supports standard amino acid coupling after conversion to an activated carboxyl derivative or after appropriate N- and side-chain protection. The guanidinium group can be managed through protection-group strategies that preserve its cationic character until final deprotection, supporting controlled assembly of D-amino-acid-containing sequences. Downstream use includes generating D-homoarginine-containing peptide analogs for studying backbone stereochemistry effects and for constructing charged interfaces in synthetic peptide libraries.
2. Chemical Biology
D-Homoarginine hydrochloride functions as a chemical biology reagent for probing recognition processes involving guanidinium-mediated interactions, including protein-binding interfaces and substrate-like motifs in enzyme systems. The extended side chain length and D-configuration can be used to modulate spatial positioning of the terminal cationic group, enabling structure-function comparisons in amino acid substitution studies. The hydrochloride salt form facilitates handling in aqueous buffers and can be leveraged for designing analogs that maintain solubility while retaining strong basicity. Conversion into protected amino acid derivatives and subsequent incorporation into labeled or modified peptide fragments supports biochemical research intermediate preparation for molecular recognition and mechanistic studies.
3. Amino Acid Derivatization
D-Homoarginine hydrochloride is suitable for amino acid derivatization and protected amino acid synthesis, where the guanidinium functionality can be selectively protected to enable orthogonal chemistry at the α-amino or α-carboxyl sites. The free carboxylic acid allows formation of esters, activated acids, or amide intermediates, supporting downstream synthesis of peptide coupling partners and chiral intermediates for fine chemical production. The strongly basic side chain can be used to generate ion-pairing reagents, zwitterionic derivatives, or conjugation handles after controlled protection and deprotection steps. Resulting derivatives can serve as intermediates for building charged peptidomimetics, conducting stereochemical SAR studies, or preparing analytical standards that distinguish D-configuration effects.
4. Bioconjugation Chemistry
D-Homoarginine hydrochloride is employed in bioconjugation chemistry where the guanidinium group provides a persistent cationic motif for electrostatic association, affinity-based capture, or incorporation into conjugate scaffolds. The amino acid backbone can be transformed into coupling-ready forms, enabling attachment to carriers such as polymers, linkers, or biomolecule-reactive intermediates while maintaining the D-configured stereocenter. Side-chain protection strategies allow controlled exposure of the guanidinium functionality at the stage required for conjugation, which can improve reproducibility of charge presentation in conjugates. Downstream applications include constructing charged linkers for biomolecule labeling, generating peptide-based conjugates for chemical biology assays, and preparing stereochemically defined reagents for binding studies.
5. Pharmaceutical Intermediate Preparation
D-Homoarginine hydrochloride is relevant to pharmaceutical intermediate preparation and process chemistry as a chiral, guanidinium-bearing amino acid precursor used to access D-amino-acid-containing building blocks for medicinal chemistry programs. The presence of both a carboxyl group and a basic guanidinium side chain supports conversion into protected amino acid derivatives compatible with peptide coupling and late-stage functionalization routes. Salt formation and controlled deprotonation behavior can be leveraged during manufacturing-style synthesis planning to manage solubility and isolate intermediates as defined salts or protected forms. Downstream utility includes producing stereochemically defined intermediates for peptidomimetic construction, SAR-focused library synthesis, and scalable preparation of charged residues used in drug-like scaffold design.
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