L-Arginine - Moligand™, 10mM in Water , CAS No.74-79-3

CAS: 74-79-3 Cat. No.: L425810 Fórmula: C₆H₁₄N₄O₂ Peso molecular: 174.20 g/mol Beilstein Registry Number: 1725413 Número CE: 200-811-1

GRADE & PURITY Moligand™, 10mM in Water

Synonyms

L-arginine|arginine|74-79-3|L-(+)-Arginine|L(+)-Arginine|L-Arg|(S)-2-Amino-5-guanidinopentanoic acid|H-Arg-OH|(L)-Arginine|Arginina|ARGININE, L-|Arginine (VAN)|L-Arginin|Argininum [INN-Latin]|Arginina [INN-Spanish]|L-Ornithine, N5-(aminoiminomethyl)-|L-al

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Visão geral

L-Arginine is an essential amino acid and precursor of nitric oxide synthesis that induces vasodilation in vivo. Nitric oxide potentiates insulin-mediated glucose uptake through the increase in blood flow.
A precursor of nitric oxide synthesis that induces vasodilation

Specifications

Sinónimos

L-arginine | arginine | 74-79-3 | L-(+)-Arginine | L(+)-Arginine | L-Arg | (S)-2-Amino-5-guanidinopentanoic acid | H-Arg-OH | (L)-Arginine | Arginina | ARGININE, L- | Arginine (VAN) | L-Arginin | Argininum [INN-Latin] | Arginina [INN-Spanish] | L-Ornithine, N5-(aminoiminomethyl)- | L-al

Especificações e pureza

Moligand™, 10mM in Water

Mecanismos bioquímicos e fisiológicos

Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.Precursor to nitric oxide synthesis. Amino acid implicated in neurotransmission, immune defences and

Condições de armazenamento de armazenamento

Store at -80°C

Enviado em

Dry ice packs + Cold packs

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Grau

Moligand™

Tipo de ação

ACTIVATOR

Nomes e identificadores

Sorrisos canónicos

C(CC(C(=O)O)N)CN=C(N)N

IUPAC Name

(2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid

InChIKey

ODKSFYDXXFIFQN-BYPYZUCNSA-N

INCHI

1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1

SMILES isoméricas

C(C[C@@H](C(=O)O)N)CN=C(N)N

WGK Alemanha

1

RTECS

CF1934200

Peso molecular

174.20 g/mol

Beilstein

1725413

Reaxy-Rn

2090768

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2090768&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acids
              • Level8 L-alpha-amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids
• Direct Parent: L-alpha-amino acids
• Alternative Parents: Fatty acids and conjugates Guanidines Amino acids Propargyl-type 1,3-dipolar organic compounds Monocarboxylic acids and derivatives Carboxylic acids Carboximidamides Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: L-alpha-amino acid - Fatty acid - Guanidine - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Carboximidamide - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Amine - Hydrocarbon derivative - Organic oxide - Primary amine - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Primary aliphatic amine - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Aliphatic acyclic compound
• Descrição: This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
• External Descriptors: Common amino acids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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Mecanismos de ação

Propriedades químicas e físicas

• Sensibilidade: Air sensitive
• Rotação específica [α]: 27 ° (C=8, 6mol/L HCl)
• Ponto de fusão (°C): 222 °C
• Peso molecular: 174.200 g/mol
• XLogP3: -4.200
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 174.112 Da
• Monoisotopic Mass: 174.112 Da
• Topological Polar Surface Area: 128.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 176.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

General laboratory preparation (literature guidance; not item-specific validation):

• Preparation of aqueous stock (1.0 M):

  • Calculate required mass: 174.20 g per liter for L-arginine free base (literature MW). For smaller volumes, scale proportionally (e.g., 17.42 g in 100 mL).
  • Add ~80% of final volume of ultrapure water, introduce arginine with stirring. Gentle warming (to ~25–30 °C) and slight acidification (few drops 1 M HCl) can accelerate dissolution if needed.
  • Adjust pH to target (commonly pH 7.4–8.0 for biochemical use) using HCl/NaOH as appropriate.
  • Bring to final volume, sterile-filter (0.22 µm) if sterility is required. Aliquot and store per Storage & Reconstitution guidance.

• Protein refolding additive screen (example):

  • Prepare buffers (e.g., 50 mM Tris, pH 8.0) containing 0, 200, 400, 600 mM L-arginine.
  • For disulfide-containing proteins, include 1–2 mM GSH/0.1–0.2 mM GSSG. Incubate denatured protein upon dilution into refolding buffers at 4–15 °C; assess recovery by activity assay and SEC.

• Chromatography aid:

  • For SEC or IEX, trial 50–200 mM arginine in eluent to reduce non-specific interactions. Verify effects on resolution and detector baseline.

Note: Concentrations, pH, and temperatures are starting points from literature and may require optimization for each system.

Biological Roles

General biochemistry (literature; not product-specific claims):

• Proteinogenic amino acid: L-Arginine is incorporated into proteins via the genetic code (codons CGU/CGC/CGA/CGG/AGA/AGG). Side-chain guanidinium participates in salt bridges and cation–π interactions central to protein folding and ligand binding.
• Metabolic pathways: A key intermediate in the urea cycle (arginase converts arginine to ornithine + urea) and nitric oxide biosynthesis (substrate for nitric oxide synthases, generating NO and citrulline). It also feeds into creatine and polyamine biosynthesis.
• Transport: Cellular uptake primarily via cationic amino acid transporters (system y+). Competition with lysine/ornithine can influence uptake kinetics in cell studies.
• pH buffering/ionic effects: While not a classical buffer at neutral pH, arginine solutions can modulate ionic strength and weakly buffer near alkaline pH due to the high pKa of guanidinium. This influences protein solubility and viscosity.
• Post-translational chemistry: Arginine residues are sites for methylation (protein arginine methyltransferases), citrullination (PAD enzymes), and can form carbonyl derivatives under oxidative stress; relevant for proteomics workflows.

Experimental considerations:

• For biochemical assays, ensure defined isomeric purity (L- vs D-). Monitor potential conversion to ornithine/citrulline in enzymatic mixtures. Use freshly prepared solutions to minimize microbial growth; sterile-filter when sterility is required.

Buffer Applications

Applicability: L-Arginine is not a classical buffer component like phosphate or HEPES, but it is widely employed as an additive in refolding and formulation buffers to mitigate aggregation and improve solubility (literature).

Practical buffer use (literature examples):

• Refolding buffers: 0.2–0.8 M L-arginine (often as HCl salt) in 20–100 mM Tris, HEPES, or phosphate, pH 7.5–8.5. Additives like redox pairs (GSH/GSSG) may be included for disulfide-containing proteins.
• Aggregation suppression: 50–500 mM arginine added to purification buffers (e.g., during ion exchange or SEC) can reduce non-specific interactions and improve recovery.
• pH considerations: With pKa(guanidinium) ~12.5, arginine contributes limited buffering near neutral pH but can increase ionic strength and modulate protein–surface interactions.
• Preparation tips: Dissolve arginine in water; adjust pH with HCl or NaOH as needed after mixing with buffer salts. Filter sterilize (0.22 µm) for biological applications. Verify conductivity/viscosity if using in chromatography.

Notes:

• The hydrochloride salt typically dissolves more rapidly and yields slightly lower solution pH. Choice between free base and salt depends on target pH and counterion constraints.
• Item-specific buffer-grade/endotoxin specifications are not provided here; consult the CoA if sterile or low-endotoxin requirements apply. Not specified for this item.

Green Alternatives

Context: L-Arginine itself is a bio-based, renewable small molecule (amino acid). Its environmental profile is generally favorable compared to many synthetic auxiliaries. Green considerations focus on sourcing, solvent systems, and process design.

Greener practice options (literature/general):

• Aqueous processing: Favor water-only formulations where feasible. Arginine’s high water solubility enables eliminating organic co-solvents in many protein and biopolymer processes.
• Bio-based sourcing: Prefer suppliers using fermentation-derived amino acids and transparent supply chains. Request documentation for origin and manufacturing where sustainability metrics are important.
• Salt choice: Arginine hydrochloride can enable lower processing temperatures and faster dissolution, potentially reducing energy input. Tradeoff: increased chloride load and conductivity.
• Minimize protecting-group chemistry: For synthetic use, adopt orthogonal protection schemes that reduce steps and enable safer deprotection (e.g., Pbf over older benzyl-type protections), minimizing hazardous solvents and reagents.
• Recovery/reuse: In large-scale bioprocesses, consider diafiltration or ion exchange to recover excess arginine from mother liquors.

Comparison (illustrative, literature):

• Arginine vs chaotropes (e.g., guanidinium chloride): Arginine offers aggregation control with less denaturation and lower environmental hazard at typical concentrations, but may require higher molar loadings and careful control of ionic strength.

Note: No item-specific environmental certifications or sourcing declarations are provided here; refer to CoA/producer documentation.

Pharmaceutical Uses

Scope: No therapeutic/clinical claims are made. The following are formulation and manufacturing roles reported in the literature for L-arginine and its salts.

Formulation roles (literature):

• Stabilizer/solubilizer: Used in biopharmaceutical protein formulations (antibodies, enzymes) to reduce aggregation, lower viscosity, and improve solubility. Arginine hydrochloride is especially common; free base can be selected to minimize chloride.
• pH/tonicity contribution: Contributes to ionic strength and can modestly affect pH in alkaline formulations; may complement buffers such as histidine, phosphate, or acetate.
• Lyophilization excipient: Functions as a bulking/stabilizing agent in freeze-dried protein products; impacts cake structure and reconstitution time.
• Process aid: Included in refolding and purification solutions to enhance yields and reduce fouling.

Regulatory/quality notes:

• Pharmacopeia: Compendial monographs exist for certain arginine forms (e.g., Arginine/Arginine Hydrochloride in USP/EP), specifying identity, assay, and purity tests. This product’s specific compliance is not stated. Not specified for this item; refer to CoA/Spec Sheet.
• Impurity control: For parenteral uses, specifications often include limits for endotoxin/bioburden, metals, and specific related amino acids. Such item-specific data are not provided here.

Manufacturing considerations:

• Validate compatibility with container/closure systems (sorption, pH drift). Monitor osmolality and viscosity at target concentrations. Perform accelerated and real-time stability indicating studies.

Physical Properties

Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.

Literature/typical physicochemical data (for L-Arginine, general reference):

• Appearance: White to off-white crystalline solid (literature)
• Melting point: Decomposes on heating; reported ~244–247 °C dec. (literature)
• Solubility: Highly soluble in water; sparingly soluble to insoluble in most organic solvents (ethanol, acetone, ether) (literature). Typical aqueous solubility can exceed 100 g/L at ambient temperature, especially for arginine salts (literature).
• pKa values (25 °C, water): pKa1 (carboxyl) ≈ 2.17; pKa2 (α-NH3+) ≈ 9.04; pKa3 (guanidinium) ≈ 12.48 (literature). The side-chain guanidinium remains protonated over a broad pH range.
• Isoelectric point (pI): ~10.76 (literature).
• LogP (octanol/water): Very hydrophilic; logP << 0; often reported as logP ~ −3 to −4 (literature, method-dependent).
• Density: Not commonly reported due to decomposition before clear melting; solid density not critical for typical aqueous uses (literature).
• Optical rotation: [α]D (c, solvent) reported in literature for L-forms; values vary by concentration/ionic strength.
• Refractive index: Not applicable for solids; solutions follow near-water refractive indices (literature).

Notes for practice:

• Strongly hygroscopic behavior is modest compared to salts; however, samples can absorb moisture/CO2 affecting apparent assay. Dry under vacuum at ambient temperature if water content control is important (general guidance). Always verify with CoA for this lot.

Quality and Grades

Item-specific details from Product Data:

• Grade/Purity: Moligand™ (brand/grade designation)
• Quality specifications (assay, water, metals, UV, endotoxin, etc.): Not specified for this item; refer to CoA/Spec Sheet.

Context and guidance:

• Moligand™ designation: A proprietary Aladdin line identifier. It is not a standardized pharmacopeial term (e.g., USP, JP, EP) nor a generic analytical grade. Users should consult the lot-specific CoA for assay/purity, residual solvents, elemental impurities, microbial/endotoxin profiles, and any stabilizers.
• Biochemical suitability: For amino acid use in biochemistry (e.g., protein work, enzyme assays), consider verifying parameters such as heavy metal content, bioburden/endotoxin, and UV background if optical assays are planned. These values are not specified here for this item.
• Trace specifications: If your application is sensitive (e.g., peptide synthesis or cell culture), request and review the CoA for: identity (NMR/IR/HRMS), optical rotation/chirality confirmation, assay by titration/HPLC, water (Karl Fischer), and known impurities (e.g., ornithine, citrulline, residual guanidines). Not specified for this item.
• Stabilizers/additives: None indicated in Product Data; if present, they would be listed on the CoA. Not specified for this item.

Reaction and Applications

Scope: As a basic, chiral α-amino acid, L-Arginine is used in biochemistry, formulation science, and as a building block for synthetic chemistry.

Biochemical/formulation applications (literature):

• Protein refolding and aggregation suppression: Arginine (often 0.2–0.8 M) is widely used to suppress non-specific protein aggregation during refolding and purification; the guanidinium side chain modulates protein–protein interactions without denaturing at moderate concentrations.
• Stabilizer/excipient: Employed in protein formulations to enhance solubility and reduce viscosity; common in mAb formulations (often as arginine HCl). Optimize ionic strength and pH for target proteins.
• Enzymology: Substrate/effector in urea cycle and nitric oxide synthase assays; used to probe arginine-binding sites in enzymes and transporters.

Synthetic/chemical applications (literature):

• Chiral building block: The L-configuration provides a handle for asymmetric synthesis. For peptide synthesis, protected derivatives (e.g., Fmoc-L-Arg(Pbf)-OH) are typically used to mask the guanidinium group.
• Derivatization: Guanidinium group can be transformed into ureas, thioureas, or engaged in guanidinylation chemistry. Direct transformations on the free base require careful protection strategies due to strong basicity and multiple nucleophilic sites.

Practical tips:

• Solution prep: Dissolve in water; slight acidification (e.g., with HCl) can speed dissolution. Filter sterilize for biological applications.
• Analytical: Monitor concentration by ninhydrin, OPA, or HPLC with derivatization (e.g., AccQ-Tag), or direct UV at 200–214 nm with appropriate blanks to subtract high background from salts.

Reaction Conditions

General guidance from literature (not item-specific specifications):

• SPPS coupling (arginine-containing residues): Fmoc strategy with side-chain protection (Pbf) is standard. Typical conditions: Fmoc-deprotection with 20% piperidine in DMF (2×5–10 min); coupling with 3–5 equiv Fmoc-Arg(Pbf)-OH, 3–5 equiv HATU or HBTU, and 6–10 equiv DIPEA in DMF for 30–60 min. Double coupling may be used for difficult sequences. Thoroughly wash to minimize guanidinium-related side reactions.
• Aqueous bioconjugation (carboxyl activation): EDC (0.5–5 mM) with NHS (molar excess) in MES or phosphate buffer, pH 5.0–6.5, 0–25 °C, minutes to hours, to form amide bonds with primary amines on biomolecules. Arginine may compete; avoid excess free arginine in reaction mixtures unless intended as a quencher.
• Refolding/formulation additions: 0.1–0.8 M arginine in buffer at pH 7–9; temperature 2–25 °C; time from minutes during dilution refolding to hours for equilibration. Monitor by SEC and DLS for aggregation.
• Derivatization of carboxyl (esterification): Prefer mild, chemoselective methods (e.g., diazomethane-free alternatives). In peptide contexts, perform esterification at protected stages to avoid guanidinium incompatibilities.

Expected outcomes and monitoring:

• Coupling efficiencies in SPPS typically >98% per step under optimized conditions; validate by Kaiser/ninhydrin tests and LC–MS of cleaved test peptides.
• In refolding, yields are protein-dependent; perform design-of-experiments varying arginine concentration, pH, and redox to optimize recovery.

Note: Replace or adapt solvents/reagents for green chemistry and safety. Always confirm compatibility with your substrates and follow SDS for each reagent.

Safety and Handling

Item-specific hazard information: Not specified for this item; consult the product SDS for authoritative safety and regulatory details.

General safety guidance (literature/standard lab practice):

• GHS/Classification: L-Arginine is widely handled in biochemical labs and is often not classified as hazardous; however, classification may vary by jurisdiction and formulation. Always defer to the SDS provided with this item.
• PPE: Safety glasses, laboratory coat, and appropriate gloves (e.g., nitrile). Use a dust mask or handle in a fume hood if fine powders become airborne.
• Handling: Avoid generation of dust. Prevent contact with eyes/skin. Wash thoroughly after handling. Use clean, dry tools to avoid cross-contamination.
• Incompatibilities: Strong oxidizers, nitrosating agents, and strong acids/bases can lead to degradation or side reactions (e.g., deamidation-like pathways under harsh conditions). Avoid prolonged heating in alkaline solutions.
• Spill/cleanup: Avoid raising dust. Sweep up and collect in appropriate container. Rinse area with water.
• First aid overview: If inhaled, move to fresh air. If on skin or in eyes, rinse with water. If ingested, rinse mouth. Seek medical attention if irritation or discomfort persists. Follow SDS guidance.
• Fire safety: Organic solid; use water spray, CO2, or dry chemical for surrounding fire. Combustion may produce nitrogen oxides and COx.
• Storage note: See Storage & Reconstitution tab for item-specific storage; maintain container tightly closed to limit atmospheric moisture/CO2 uptake.

Solvent Selection

Relevance: L-Arginine is a highly polar, basic amino acid. Solvent considerations are primarily about preparing aqueous solutions and adjusting ionic strength/pH.

General solvent behavior (literature):

• Polarity/miscibility: Freely soluble in water; essentially insoluble or very sparingly soluble in most aprotic organics (acetone, acetonitrile, ethers) and low-solubility in alcohols. Solubility markedly increases as the hydrochloride or other salts.
• Dielectric environment: High-dielectric media (water, water–buffer) stabilize the guanidinium cation and carboxylate, favoring dissolution.
• pH effects: Solubility and charge state depend on pH; arginine remains cationic up to very basic pH due to the high pKa of guanidinium (~12.5). Slight acidification (e.g., HCl) can expedite dissolution.

Practical selection tips:

• Preparation of concentrates: 0.1–1.0 M arginine solutions are routinely prepared in water or buffers (literature). Warm to room temperature and stir to accelerate dissolution; adjust pH as needed.
• Buffers: Use standard biological buffers (e.g., phosphate, HEPES, Tris) and add arginine as an excipient/additive. Note that Tris/arginine can lead to high ionic strength; check assay compatibility.
• Organic co-solvents: Generally not recommended; if viscosity reduction or solubility tuning is needed, small fractions of ethanol or isopropanol may be used in some protein formulations, but compatibility must be validated.

Comparison (general):

• L-Arginine vs L-Lysine: Arginine typically provides stronger aggregation suppression in protein refolding/stabilization due to guanidinium-specific interactions (literature), but may raise conductivity more at equal mass concentrations.

Storage and Reconstitution

Item-specific storage and shipping (from Product Data):

• Storage Conditions: Store at −80 °C.
• Shipped In: Dry ice packs + Cold packs.

General guidance (literature/standard practice):

• Solid material: Keep container tightly closed to minimize moisture and CO2 uptake. Allow to equilibrate to room temperature in a desiccator before opening to prevent condensation.
• Reconstitution: Dissolve in ultrapure water or buffer to the desired concentration (commonly 0.1–1.0 M for stock solutions). Adjust pH as required (slight acidification can speed dissolution). Filter sterilize if needed.
• Aliquoting: For long-term storage of solutions, prepare single-use aliquots to avoid repeated freeze–thaw. Store at −20 °C to −80 °C depending on application.
• Stability: Item-specific solution stability, impurity limits, and endotoxin specifications are not provided here. Not specified for this item; refer to CoA/Spec Sheet. In general, aqueous amino acid solutions are stable for weeks at 2–8 °C and months frozen; verify by HPLC before critical use.
• Freeze–thaw: Minimize cycles; thaw on ice or at room temperature and mix gently to avoid precipitation due to localized pH changes.

Disposal: Dispose of unused solutions according to institutional and local regulations for non-hazardous aqueous organic waste, unless your process introduces hazardous contaminants.

Structure and Identity

Brief overview: L-Arginine is a basic, proteinogenic α-amino acid bearing a strongly basic guanidinium side chain. It is chiral (L-configuration) and commonly exists as a zwitterion in water.

Item-specific identifiers (from Product Data):

• SKU: L425810
• Product Name: L-Arginine
• CAS: 74-79-3
• CID: 6322
• InChIKey: 254984 (as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature structural identity (general reference, not item-specific):

• Molecular formula: C6H14N4O2 (literature)
• Molecular weight: 174.20 g/mol (literature)
• IUPAC name: (S)-2-amino-5-guanidinopentanoic acid (literature)
• Canonical SMILES (typical): NC@@HC(=O)O (literature)
• InChIKey (typical): ODHCTXKNWHHXJC-BYPYZUCNSA-N (literature)

Structural features (general chemistry):

• Functional groups: α-amino (–NH2/–NH3+), α-carboxyl (–CO2H/–CO2−), and a guanidinium side chain (–NHC(=NH)NH2) that is protonated across physiological pH ranges.
• Stereochemistry: Single stereocenter at Cα; this product refers to the L-enantiomer (S at Cα in most conventions for amino acids).
• 2D description: A five-carbon backbone attaches the α-carbon (bearing NH2 and CO2H) to a terminal guanidinium group; at neutral pH, the carboxylate is deprotonated and both α-amino and side-chain guanidinium are protonated, yielding a doubly cationic zwitterion.

Synthetic Utility

Chemical reactivity (literature):

• Functional groups: α-Carboxyl (acylation/amide formation), α-amino (nucleophilic; typically protected as Boc/Fmoc), and side-chain guanidinium (strong base, resonance-stabilized; typically protected with acid-labile groups such as Pbf or Mtr in peptide synthesis).
• Peptide synthesis: L-Arginine is a cornerstone residue in SPPS and solution-phase peptide assembly. Free base is seldom used directly; instead, protected derivatives like Fmoc-L-Arg(Pbf)-OH facilitate selective coupling and minimize side reactions.
• Derivatization avenues: Conversion to Nα-acyl derivatives, esterification of the carboxyl (for prodrug-like or intermediate purposes), and guanidinylation chemistry via isothiourea or CDI-based strategies.
• Chiral pool: The L-stereocenter can transfer asymmetry in constructing chiral amines, lactams, and heterocycles via strategic fragmentation (e.g., through ornithine/citrulline pathways) or cyclizations yielding guanidinium-containing scaffolds.

Practical notes:

• Protection strategy: For chemoselective transformations, protect the α-amino (Fmoc/Boc) and guanidinium (Pbf/Mtr/Tos). Avoid strong bases/oxidants that can degrade guanidinium.
• Coupling conditions: Employ modern peptide coupling reagents (HATU/HBTU/DIC+Oxyma) under DMF/NMP with controlled base (DIPEA). For solution-phase amidation, water-compatible carbodiimides (EDC) with NHS activation enable aqueous coupling to biomolecules.
• Analytics: Characterize derivatives by HRMS and 2D NMR; guanidinium protons often show characteristic downfield shifts and broadened signals due to exchange.

Target Specificity

Not applicable. This product is a small-molecule amino acid, not an antibody or affinity reagent. No antigen/epitope specificity, species reactivity, clone, or isotype information applies.