L-Homoarginine is a naturally occurring basic amino acid in which the side chain extends the guanidinium-containing motif of arginine by one methylene unit, giving a longer aliphatic linker between the α-amino group and the terminal strongly basic functionality. The molecule contains an α-amino group and an α-carboxyl group alongside a terminal guanidinium group that can participate in salt formation and hydrogen-bonding, and its stereochemistry is specified as L by the product name. L-Homoarginine is used as a free amino acid building block for peptide synthesis and as a substrate or reference compound in amino acid analysis, enabling studies that compare side-chain length effects on peptide structure, charge distribution, or binding interactions.
CAT No: CP06101
CAS No:1483-01-8
Synonyms/Alias:L-Homoargininehydrochloride;1483-01-8;(S)-2-Amino-6-guanidinohexanoicacidhydrochloride;L(+)-Homoargininehydrochloride;L-HOMOARGININEHCL;MFCD00012622;SBB067122;L-(+)-Homoargininehydrochloride;H-HomoArg-OH.HCl;PubChem23755;AC1MC3WI;H-L-HOARG-OHHCL;homo-L-argininehydrochloride;KSC491O4N;H1007_SIGMA;SCHEMBL7101494;Jsp002780;CTK3J1746;MolPort-003-936-110;N6-(aminoiminomethyl)-L-Lysine;EBD15013;AN-248;ANW-21129;AKOS015924239;AM82551
L-Homoarginine is a naturally occurring, basic amino acid homolog of arginine featuring an additional methylene unit in the side chain, yielding a guanidinium group positioned for strong cationic interactions. The molecule contains a stereogenic center at the alpha carbon in the L-configuration, alongside a free carboxylic acid and a primary amino group that can be selectively protected or left unprotected depending on the synthetic objective. The side-chain guanidinium functionality is strongly polar, remains protonated under mildly acidic conditions, and participates in salt formation, hydrogen bonding, and nucleophilic/acid-base chemistry relevant to derivatization and peptide coupling. As a chiral amino acid building block and biochemical research intermediate, L-homoarginine can be incorporated into peptide and peptidomimetic scaffolds or converted into protected derivatives that support stepwise synthesis and downstream functional group transformations.
1. Peptide Synthesis
L-Homoarginine supports peptide building block preparation and coupling chemistry in solid-phase or solution-phase workflows where guanidinium-containing residues require controlled protection strategies. The alpha-amino and alpha-carboxyl groups enable amide bond formation, while the side-chain guanidinium can be protected as a removable guanidinium-protecting group to suppress undesired salt formation and side reactions during peptide assembly. L-homoarginine's L-stereochemistry provides stereodefined incorporation at the residue level, supporting consistent conformational and charge patterns in longer sequences. Resulting homoarginine-containing peptides and peptide fragments can be used for mechanistic studies of basic residue recognition, for generating sequence-defined materials, and for building analog libraries that probe how extended side-chain length influences structure and binding.
2. Chemical Biology Tools
L-Homoarginine is suitable for chemical biology research where cationic guanidinium chemistry is used to tune electrostatic interactions and biomolecular recognition. The extended side chain relative to arginine can modulate spacing between the guanidinium charge and the peptide backbone, enabling design of probes that interact with nucleic acids, acidic protein surfaces, or glycosaminoglycans through multivalent hydrogen bonding and ionic contacts. Derivatization of the alpha-amino or carboxyl group into protected intermediates can facilitate conjugation handles for labeling, affinity capture, or imaging reagent synthesis. Downstream, homoarginine-containing conjugates can serve as research intermediates for studying binding specificity, charge-driven uptake, and the role of basic residue topology in biomolecular assemblies.
3. Amino Acid Derivatization
L-Homoarginine can be converted into protected amino acid derivatives and functionalized intermediates for synthetic organic chemistry and biochemical reagent preparation. The guanidinium group can be temporarily masked to enable selective transformations at the alpha-amino and carboxyl functionalities, including esterification for solubility control or activation for coupling to form amide, urea, or related linkages. The presence of a defined L-chiral center allows stereochemically consistent downstream products, including chiral intermediates used in peptide analog synthesis and stereopure reference standards. Functionalized homoarginine derivatives can further undergo side-chain-compatible modifications such as salt formation, controlled deprotection, and conjugation-ready intermediate generation for fine chemical synthesis and applied research workflows.
4. Peptidomimetics And SAR Studies
L-Homoarginine is applicable to peptidomimetic construction and structure-activity relationship studies that evaluate how basic residue geometry influences receptor or enzyme recognition. The guanidinium moiety provides a canonical hydrogen-bonding and charge motif, while the extra methylene length relative to arginine can shift the spatial presentation of the cationic center within a scaffold. Incorporation into constrained analogs, backbone-modified peptides, or side-chain substituted derivatives can support systematic SAR mapping of charge density, distance effects, and conformational preferences. Homoarginine-derived fragments can also serve as chiral building blocks for generating focused libraries of basic-residue variants used in molecular design and binding characterization.
5. Pharmaceutical Manufacturing Intermediates
L-Homoarginine can function as a process-relevant amino acid intermediate for manufacturing routes that require stereopure, guanidinium-bearing fragments for API-adjacent synthesis. The combination of an alpha-amino group, carboxylic acid, and protected guanidinium chemistry enables stepwise conversion into coupling-ready forms, supporting controlled assembly of peptide-like linkers and guanidinium-containing motifs in specialty intermediates. Protecting-group strategies for the guanidinium functionality can be integrated into industrially scalable synthetic sequences to manage solubility, minimize side reactions, and enable selective deprotection at defined stages. Downstream products derived from L-homoarginine can be used as defined intermediates for fine chemical production where consistent stereochemistry and reliable functional-group handling are required in applied manufacturing chemistry.
6. Analytical Research Standards
L-Homoarginine is suitable for analytical research and method development requiring defined basic amino acid standards and chiral reference materials. The stereochemically pure L-configuration and the strongly polar guanidinium group make the compound a useful benchmark for chromatographic behavior and derivatization-based detection strategies targeting amino acids and related guanidinium species. Formation of salts and controlled derivatization of the alpha-amino and carboxyl groups can generate stable analytical forms that improve detectability in mass spectrometry or other analytical platforms. Homoarginine-based standards and derivatives can support quantitative method validation workflows, impurity profiling, and comparative analysis of amino acid homologs in biochemical research and industrial quality control contexts.
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