DL-Homoarginine hydrochloride is a salt form of the non-proteinogenic amino acid homoarginine, featuring an extended guanidinium-containing side chain relative to arginine and a free α-amino group and α-carboxyl group on the same carbon backbone. The hydrochloride counterion associates with the basic guanidinium functionality, and the "DL" designation indicates a racemic mixture of stereoisomers at the α-carbon. As an amino acid salt, it is used as a precursor for preparing homoarginine-containing peptide analogues and for chemical biology or analytical workflows that require a defined guanidinium-bearing amino acid building block.
CAT No: CP06103
DL-Homoarginine hydrochloride is a hydrochloride salt of DL-homoarginine, an amino acid analog featuring an extended carbon chain relative to arginine and a guanidinium-containing side chain. The molecule presents a primary amino group and a carboxylic acid functionality (commonly handled as the salt form), along with a strongly basic guanidinium moiety that can participate in salt formation, hydrogen bonding, and ionic interactions. The DL designation indicates a racemic mixture at the α-carbon, which impacts stereochemical outcomes in peptide coupling and downstream chiral resolution strategies. The salt form improves handling and solubility for synthetic and analytical workflows, while the guanidinium group typically requires protection or controlled conditions to maintain compatibility with peptide coupling chemistry.
1. Peptide Synthesis
DL-Homoarginine hydrochloride is applied in peptide building block preparation and peptide coupling development where a guanidinium-bearing side chain is required for arginine-mimetic recognition. The amino acid backbone supports standard N- and C-terminal functionalization, while the basic guanidinium side chain can be protected or temporarily masked to prevent side reactions during amide bond formation. Racemic stereochemistry enables studies of stereochemical effects on coupling efficiency and on the conformational behavior of homoarginine-containing sequences. Downstream, protected derivatives can be incorporated into peptides for generating arginine-like cationic motifs used in structure-function investigations and peptidomimetic design.
2. Amino Acid Derivatization
DL-Homoarginine hydrochloride is used as a chemical intermediate for amino acid derivatization routes targeting guanidinium-functional materials and ionic pharmacophore scaffolds. The guanidinium group enables selective transformations such as controlled protection/deprotection strategies, salt exchange, and conjugation handles that can be tuned for solubility and reactivity. The presence of both an α-amino group and a carboxyl group supports formation of activated esters, amides, and other downstream functional derivatives used in fine chemical synthesis. Racemic availability can be leveraged for process development studies where stereochemical separation is performed later to access enantiopure homoarginine derivatives when needed.
3. Chemical Biology Labeling
DL-Homoarginine hydrochloride can be employed in chemical biology workflows that require cationic guanidinium chemistry for binding assays, surface immobilization, and biomolecular interaction mapping. The side-chain guanidinium functionality provides strong electrostatic and hydrogen-bonding interactions with nucleic acids, acidic protein regions, and other anionic targets, enabling design of labeling reagents or affinity probes after appropriate functional group modification. The hydrochloride salt form facilitates aqueous handling during derivatization steps that introduce linker groups for conjugation to biomolecules. Incorporation into peptide analogs or conjugates supports downstream studies of molecular recognition, charge-driven binding, and competitive interaction profiling.
4. Protein Engineering Studies
DL-Homoarginine hydrochloride is suitable for protein engineering and protein modification research where arginine-like side-chain geometry and charge distribution are explored in engineered variants. The extended methylene chain relative to arginine can alter local spacing of the guanidinium group, making homoarginine-containing constructs useful for probing residue-level effects on folding, binding interfaces, and electrostatic networks. The amino acid's functional groups support incorporation into synthetic segments followed by assembly into larger biomolecular constructs, including peptide-to-protein workflows. Racemic starting material may be used in early-stage scaffold generation, with later stereochemical refinement applied when enantiopure residues are required for mechanistic interpretation.
5. Pharmaceutical Intermediate Synthesis
DL-Homoarginine hydrochloride is applied in pharmaceutical intermediate preparation where guanidinium-bearing amino acid derivatives serve as precursors for cationic side-chain motifs in drug-like scaffolds. The protected amino acid chemistry compatible with peptide coupling and amide formation enables conversion into N-protected or C-activated intermediates used for constructing heteroatom-rich, strongly basic pharmacophore elements. The hydrochloride salt supports handling during industrially relevant synthesis planning, including salt management and downstream purification by exploiting ionic properties. Racemic supply can support process route screening for subsequent chiral resolution or asymmetric conversion, aligning with common fine chemical manufacturing strategies for amino acid-derived intermediates.
6. Process Chemistry and Fine Chemicals
DL-Homoarginine hydrochloride is utilized in process chemistry and specialty chemical production as a controllable, salt-form amino acid feedstock for producing protected homoarginine derivatives and downstream functionalized intermediates. The combination of α-amino, carboxylic acid, and guanidinium groups enables staged protection logic that can be integrated into manufacturing sequences for peptide building blocks and guanidinium-containing specialty reagents. The racemic nature supports cost-effective sourcing for routes where stereochemistry is addressed later, while the salt form can simplify material transfer and formulation during intermediate preparation. The resulting derivatives can then be directed toward peptide science, peptidomimetic construction, and other amino acid chemistry programs requiring guanidinium functionality.
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