N-α-Acetyl-L-arginine dihydrate

N-α-Acetyl-L-arginine dihydrate is an N-acetylated L-arginine derivative that retains the arginine side chain with a stereodefined α-carbon and a guanidinium functionality capable of strong hydrogen bonding and salt formation. The molecule contains an amide-forming N-acetyl group at the α-amino position and a free carboxylic acid, giving a zwitterionic character under aqueous conditions while modulating nucleophilicity relative to unprotected arginine. The dihydrate form indicates defined water association, which can influence handling, crystallization behavior, and reproducibility in solution-based biochemical assays. As a chiral amino acid intermediate with a guanidinium side chain, N-α-Acetyl-L-arginine dihydrate participates in peptide coupling chemistry as an arginine-containing building block precursor and can undergo controlled salt formation, derivatization, or further functional transformations for downstream synthetic and analytical workflows.

1. Peptide Coupling Chemistry

N-α-Acetyl-L-arginine dihydrate is applied in peptide synthesis workflows where an N-acetylated arginine motif is required to model N-terminal capping or to generate defined peptide analogs. The protected α-amide (from N-acetylation) and the free carboxylic acid enable orthogonal coupling strategies using standard peptide coupling reagents, while the guanidinium side chain can be managed through salt formation or compatible protection approaches during assembly. Incorporation of this L-arginine derivative supports construction of short peptides and peptidomimetics that preserve guanidinium-mediated recognition while maintaining an N-acetylated backbone environment. The resulting peptide intermediates and analogs can be carried into structure-activity relationship studies and biochemical characterization of arginine-dependent interactions.

2. Enzyme Substrate Studies

N-α-Acetyl-L-arginine dihydrate is utilized in biochemical research aimed at probing enzyme specificity toward arginine-containing substrates and N-terminally modified amino acid derivatives. The molecule's guanidinium group provides a strongly basic recognition handle that can participate in enzyme active-site binding, while the N-acetylation at the α-amino position can mimic N-terminal acetylation patterns found in protein contexts. The free carboxylate supports productive positioning for enzyme-mediated processing or binding assays, and the stereochemically defined L-configuration maintains consistency with chiral substrate requirements. Downstream use includes generating assay-ready standards, preparing related analogs for kinetic comparisons, and supporting mechanistic studies that differentiate N-acetylated versus unmodified arginine substrates.

3. Chemical Biology Labeling

N-α-Acetyl-L-arginine dihydrate serves in chemical biology and biomolecule modification programs where arginine guanidinium chemistry is leveraged for affinity labeling and conjugation design. The guanidinium side chain can be exploited for strong ionic and hydrogen-bond interactions with complementary binding motifs, while the N-acetylated backbone provides a defined amide environment that can reduce unwanted side reactions during conjugation. The presence of a carboxylic acid enables formation of activated esters or coupling handles for attachment to linkers, surfaces, or carrier scaffolds under controlled conditions. The resulting labeled arginine-containing constructs can support binding studies, reagent development for molecular recognition assays, and preparation of analytical probes derived from amino acid chemistry.

4. Chiral Amino Acid Intermediate Synthesis

N-α-Acetyl-L-arginine dihydrate is used as a chiral amino acid intermediate in synthetic organic chemistry when an N-acetylated arginine stereocenter is needed as a downstream feedstock. The compound's defined L-configuration and functional group set (carboxylic acid, N-acetyl amide, guanidinium) can guide stepwise derivatization toward protected amino acid derivatives, guanidinium-compatible intermediates, or peptide building blocks with controlled N-terminal identity. The dihydrate form can be relevant for reproducible solid handling and crystallization in process-oriented workflows that require consistent starting material behavior. Prepared derivatives can then be routed into fine chemical synthesis, including the manufacture of arginine-containing intermediates used for peptide analog libraries and specialty reagents.

5. Analytical Standard Development

N-α-Acetyl-L-arginine dihydrate is applicable to analytical research as a reference compound for method development and quantitation of N-acetylated arginine species in complex matrices. The stable N-acetyl amide and guanidinium functionality provide characteristic chromatographic and mass spectrometric signatures, supporting identification and calibration in workflows such as amino acid profiling and peptide hydrolysate analysis. The stereochemical integrity of the L-configuration helps ensure that standards reflect biologically relevant stereochemistry when separating enantiomeric or epimeric species. Downstream use includes supporting quality control for synthetic peptide intermediates, verifying derivatization completeness, and enabling routine monitoring of N-terminal acetylation patterns in research-grade sample sets.

6. Pharmaceutical Intermediate Preparation

N-α-Acetyl-L-arginine dihydrate is relevant to pharmaceutical intermediate preparation where controlled arginine functionality and defined N-terminal modification are required for downstream synthesis of peptide-like building blocks. The N-acetylated α-amino group provides an amide-stabilized nitrogen that can be carried through multi-step syntheses to maintain backbone identity, while the guanidinium side chain supports subsequent transformation into protected or activated forms compatible with peptide assembly. The free carboxylic acid supports coupling or conversion into activated intermediates for incorporation into larger fragments used in peptidomimetic construction. Industrially, this amino acid derivative can serve as a reproducible chiral starting material for specialty chemical production routes that target arginine-containing structures used in research and manufacturing supply chains.

1. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis

2. Cationic cell-penetrating peptides are potent furin inhibitors

3. Glucagonlike peptide 2 analogue teduglutide: stimulation of proliferation but reduction of differentiation in human Caco-2 intestinal epithelial cells

4. Immune responses to peptides containing homocitrulline or citrulline in the DR4-transgenic mouse model of rheumatoid arthritis

5. Immune-awakening Saccharomyces-inspired nanocarrier for oral target delivery to lymph and tumors