Fmoc-D-Homoarginine is an Fmoc-protected, D-configured non-proteinogenic amino acid derivative featuring an extended guanidinium-containing side chain characteristic of homoarginine. The molecule bears an Fmoc carbamate on the α-amino group and a free carboxylic acid, while the side chain contains a strongly basic guanidinium functionality that can participate in ionic and hydrogen-bonding interactions. In peptide chemistry and chemical biology, it is used as a protected building block for incorporating the homoarginine motif into peptide sequences via stepwise coupling, and the guanidinium handle supports studies of charge-driven binding and structure-activity relationships in synthetic analogs.
CAT No: CP06108
Fmoc-D-Homoarginine is an Fmoc-protected D-configured amino acid derivative featuring a side chain guanidinium functionality characteristic of the homoarginine family. The molecule combines an N-(9H-fluoren-9-ylmethoxycarbonyl) protecting group with a stereogenic center at the alpha carbon, enabling controlled peptide coupling while preserving the D-configuration through standard solid-phase or solution-phase workflows. The side-chain guanidinium group is strongly polar and can participate in salt formation and hydrogen-bonding networks, while the protected carboxylate is typically handled as the free acid during peptide assembly or converted to activated derivatives for intermediate chemistry. The Fmoc carbamate can be removed under base-promoted conditions, exposing the amino group for sequential peptide bond formation and downstream derivatization in amino acid chemistry and peptide science.
1. Peptide Synthesis
Fmoc-D-Homoarginine is applied in peptide building block preparation for automated solid-phase peptide synthesis and solution-phase peptide coupling where D-amino acid incorporation is required. The Fmoc-protected alpha-amine supports orthogonal deprotection, while the guanidinium-bearing side chain enables formation of peptide segments that mimic arginine-like charge patterns in peptidic sequences. The D stereochemistry can be retained through coupling and deprotection cycles, supporting stereodefined peptide analog construction for backbone modification studies. The resulting D-homoarginine-containing peptides can be used as research materials for studying how guanidinium-mediated interactions influence folding, binding, and molecular recognition.
2. Peptidomimetics
Fmoc-D-Homoarginine serves as a chiral input for peptidomimetic construction in chemical biology and medicinal chemistry research programs focused on charge-directed binding motifs. The side-chain guanidinium group provides a persistent cationic interaction handle, while the Fmoc-protected amine allows iterative assembly of constrained or modified peptide scaffolds. D-configuration at the alpha carbon supports incorporation of non-natural stereochemical elements that can alter conformational preferences and protease susceptibility in peptide analogs. Downstream derivatives prepared from the assembled peptidomimetics can be used for structure-activity relationship studies and molecular design iterations where guanidinium positioning is a key variable.
3. Side-Chain Functionalization
Fmoc-D-Homoarginine supports amino acid derivatization strategies targeting guanidinium chemistry, including salt-state tuning, protected-group exchange, and conjugation-ready intermediate generation after Fmoc removal. The guanidinium functionality can be carried through peptide coupling steps and then leveraged for subsequent transformations such as controlled formation of ionic complexes or attachment to electrophilic coupling partners under conditions compatible with peptide-derived substrates. The D stereocenter provides stereochemical control for downstream analog libraries where stereodependence of guanidinium-mediated interactions is evaluated. Functionalized products derived from D-homoarginine segments can be used as intermediates for biomolecule modification and as defined charged fragments in synthetic organic chemistry.
4. Chemical Biology Research
Fmoc-D-Homoarginine is suitable for chemical biology workflows that require defined D-amino acid content and arginine-mimetic side-chain charge. The Fmoc-protected amino group enables reproducible peptide assembly, while the guanidinium-bearing side chain supports electrostatic and hydrogen-bonding interactions relevant to receptor binding, nucleic acid association, and protein-surface recognition assays. D-homoarginine incorporation can be used to probe stereochemical effects on binding interfaces and to generate peptide probes with altered proteolytic stability profiles for experimental interrogation. Resulting D-homoarginine-containing probes can function as sequence-defined tools for studying molecular recognition and for mapping interaction determinants in biochemical research.
5. Pharmaceutical Manufacturing
Fmoc-D-Homoarginine is applicable to industrial peptide intermediate preparation where controlled stereochemistry and orthogonal protection are required for process-compatible synthesis. The Fmoc carbamate protecting group supports standard deprotection logic for exposing the amino functionality during stepwise peptide construction, while the guanidinium side chain provides a defined polar functionality that can be carried through manufacturing routes. D-homoarginine-containing intermediates can be used in the production of peptide analogs and peptidomimetic materials where non-natural stereocenters are built into the sequence to meet specific synthetic specifications. The compound's structure aligns with fine chemical synthesis practices that emphasize reproducible protection/deprotection behavior and downstream scaffold generation from protected amino acid building blocks.
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