L-Glutamic acid alpha-(4-methoxy-beta-naphthylamide) - ≥98% , CAS No.74938-90-2

CAS: 74938-90-2 Cat. No.: L1014351 Numero EC: 636-154-6 PubChem CID: 7015691

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

Sorrisi canonici

COC1=CC(=CC2=CC=CC=C21)NC(=O)C(CCC(=O)O)N

IUPAC Name

(4S)-4-amino-5-[(4-methoxynaphthalen-2-yl)amino]-5-oxopentanoic acid

InChIKey

JKMBFBPDQHOZTG-ZDUSSCGKSA-N

INCHI

1S/C16H18N2O4/c1-22-14-9-11(8-10-4-2-3-5-12(10)14)18-16(21)13(17)6-7-15(19)20/h2-5,8-9,13H,6-7,17H2,1H3,(H,18,21)(H,19,20)/t13-/m0/s1

Isomeri SMILES

COC1=CC(=CC2=CC=CC=C21)NC(=O)[C@H](CCC(=O)O)N

CAS alternativo

74938-90-2

PubChem CID

7015691

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 Glutamic acid and derivatives

• 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
• Direct Parent: Glutamic acid and derivatives
• Alternative Parents: Alpha amino acid amides Naphthalenes Methoxyanilines Anisoles N-arylamides Alkyl aryl ethers Fatty amides Quaternary ammonium salts Secondary carboxylic acid amides Carboxylic acid salts Monocarboxylic acids and derivatives Carboxylic acids Hydrocarbon derivatives Monoalkylamines Carbonyl compounds Organic oxides Organic salts Organic zwitterions
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Glutamic acid or derivatives - Alpha-amino acid amide - Naphthalene - Methoxyaniline - Anisole - Phenol ether - N-arylamide - Alkyl aryl ether - Fatty amide - Fatty acyl - Benzenoid - Quaternary ammonium salt - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid salt - Ether - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Primary aliphatic amine - Organonitrogen compound - Organooxygen compound - Organic zwitterion - Organic salt - Hydrocarbon derivative - Carbonyl group - Organic oxide - Amine - Organic oxygen compound - Aromatic homopolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

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

Proprietà chimiche e fisiche

• Peso molecolare: 302.320 g/mol
• XLogP3: -1.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 302.127 Da
• Monoisotopic Mass: 302.127 Da
• Topological Polar Surface Area: 102.000 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 402.000
• 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

• Item-specific
  • No tested applications or recommended dilutions are provided.
• General usage examples (for similar compounds; adjust to your system)
  • Stock solution prep: Dissolve in anhydrous DMSO at 10–50 mM. Sonication or gentle warming (≤35 °C) can assist dissolution. Filter through a 0.22 μm PTFE filter if needed.
  • Enzymatic assay development (conceptual): Combine a derivative bearing the MNA chromophore with the enzyme of interest in buffered aqueous media (pH 7–8); monitor increase/decrease of UV/fluorescence signal at the naphthyl band. Calibrate with known standards.
  • Peptide coupling: Activate the γ-CO2H with HATU (1.1 eq) in DMF, add DIPEA (2 eq) and amine nucleophile (1.1 eq), stir at rt for 2–4 h; quench, work up, and purify by RP-HPLC using aqueous MeCN with 0.1% formic acid.
• Note: These are illustrative protocols for analogous materials, not validated for this specific item.

Biological Roles

• Item-specific (from Product Data)
  • No biological role claims are specified; product is for research use only.
• General context
  • L-Glutamic acid is a central amino acid in metabolism and protein structure. In modified forms, such as naphthylamide conjugates, it serves as a reporter-bearing analog for biochemical studies rather than a native metabolite.
  • Naphthylamide tags are commonly employed to enable UV/fluorescence detection of enzyme activity, peptide transport, or binding events. The 4-methoxy substituent generally enhances chromophoric properties compared to unsubstituted 2-naphthylamide.
  • Potential research uses include:
    • Tracking peptide coupling or hydrolysis by monitoring the naphthyl signal.
    • Serving as a structural element in peptidomimetic libraries where the glutamate side chain provides an acidic handle for interaction profiling.
  • Note: The presence of the bulky hydrophobic naphthylamide alters native biological behavior. Any interpretations should consider this non-natural modification. No medical or clinical use is implied or supported.

Buffer Applications

This compound is not a conventional buffering agent. It possesses one carboxylic acid and one primary amine, but its pKa values and hydrophobic chromophore make it unsuitable as a defined buffer system.

• Practical notes (general)
  • For aqueous work, dissolve in standard laboratory buffers (e.g., phosphate, HEPES, Tris) adjusted to maintain solubility and the desired ionization state. Typical assay pH ranges: 6.5–8.5.
  • Adjust pH cautiously when preparing concentrated aqueous stocks to avoid local precipitation; consider first preparing a DMSO stock.

Green Alternatives

This item is a solid amino acid derivative, not a bulk process solvent. “Green alternatives” pertain to how you use it in synthesis/assays.

• Greener handling strategies (general)
  • Prefer water or aqueous buffer as the final medium for assays; use minimal DMSO/DMF as co-solvents (≤1–2% v/v) to reduce organic solvent burden.
  • For peptide couplings, consider greener coupling reagents/conditions (e.g., water-compatible carbodiimide chemistry EDC/HOAt alternatives, or enzyme-mediated ligations) to reduce hazardous waste.
  • Replace DMF with safer polar aprotics where feasible (e.g., NBP, PC, Cyrene) after validating solubility and reaction performance.

Small comparison (general guidance; validate for your system)

• Conventional vs alternative media:

  • DMF/DMSO: Excellent solubility; regulatory and disposal footprint higher.
  • N-Butylpyrrolidone (NBP) or PolarClean: Safer profiles; may require longer reaction times or higher temperatures.
  • Aqueous-buffered ethanol or 2-propanol cosolvent systems: Reduce toxicity; ensure compatibility with targets/assays.

• Waste minimization

  • Use HPLC with aqueous-rich gradients to limit ACN/MeOH consumption.
  • Opt for solid-phase extraction with water-wettable sorbents to decrease chlorinated solvent use.

Pharmaceutical Uses

• Item-specific (from Product Data)
  • No pharmacopeial grade or excipient designation is provided.
  • Research use only; not for human or veterinary use.
• General
  • Naphthylamide-bearing amino acid derivatives are primarily analytical/biochemical reagents rather than formulation excipients. They may be employed as reference standards, assay substrates, or synthetic intermediates in discovery workflows but are not typically included in dosage forms.
  • If used in regulated environments, control documents should include full analytical characterization (identity/purity), stability data, and impurity profiles specific to the lot used.

Physical Properties

• Item-specific (from Product Data)
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • No item-specific BP/MP/solubility/logP/pKa/refractive index provided.
• Literature/computed values (context; not product specifications)
  • Approximate molecular formula and mass for the described structure: C16H18N2O4; Mr ≈ 302.33 g/mol (computed by atom summation).
  • Ionizable groups and typical pKa (amino acid analogs, literature):
    • γ-carboxylic acid pKa ~4.0–4.5 (carboxylates in water).
    • α-amine pKaH ~8.5–9.5 (protonated ammonium on amino acids).
    • Amide is non-basic, non-ionizable under physiological pH.
  • Solubility tendencies (general): cationic/anionic forms are water-soluble; the naphthylamide increases hydrophobicity. Practical dissolution often uses polar protic/aprotic solvents (water at adjusted pH, aqueous buffers, DMSO, DMF) before dilution.
  • UV/fluorescence (naphthylamide chromophore, literature): 4-methoxy-2-naphthylamide groups exhibit strong UV absorbance in the 230–330 nm region and show environment-dependent fluorescence; exact λmax/ε depend on substitution and medium.
• Practical notes
  • For assay work, prepare a concentrated stock in anhydrous DMSO or DMF, then dilute into aqueous buffer to minimize precipitation. Determine exact solubility empirically for your medium.

Quality and Grades

• Item-specific (from Product Data)
  • Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting grade (general guidance)
  • For reagents used in biochemical assays (chromogenic/fluorogenic amino acid derivatives), key quality attributes typically include high chemical purity, low residual solvents, and well-defined water content. When applicable, HPLC purity provides confidence for kinetic measurements.
  • If offered as “assay grade” or “≥98% (HPLC)”: indicates suitability for analytical/biochemical applications with minimal UV-active impurities that could interfere with detection. Low metal content is generally less critical for this class compared to catalysts, but trace acids/bases can affect stability.
• What to look for on the CoA (practical checklist)
  • Identification (NMR/IR/MS) consistent with the naphthylamide structure.
  • Purity by HPLC/GC and residual solvent content.
  • Water content (Karl Fischer) if hygroscopicity is a concern.
  • Appearance and UV profile of the chromophore.
  • If chiral: verification of L-configuration (e.g., optical rotation or chiral HPLC).

Reaction and Applications

• Item-specific applications (from Product Data)
  • Manufacturer applications: Not specified in the listing beyond “For research use only.”
• Literature/practice (context for this class of compounds)
  • Naphthylamide-tagged amino acids are widely used as chromogenic/fluorogenic building blocks and as components of enzyme substrates. The 4-methoxy-2-naphthylamide (MNA) group provides strong UV absorbance and modest fluorescence, facilitating spectroscopic tracking of reactions.
  • Example applications:
    • Synthesis of γ-glutamyl conjugates and peptidomimetics where the α-carboxyl is capped as an anilide; the free α-amine can be coupled to protect/unprotect sequences or immobilize on resins.
    • Preparation of fluorometric substrates after further elaboration (e.g., linking the γ-carboxyl to leaving groups or donors) for studying glutamyl-processing enzymes. MNA-tagged amides enable HPLC/UV quantification.
    • Use as a reporter-bearing amino acid in peptide coupling studies, providing built-in UV detection during purification.
  • Practical notes:
    • Maintain anhydrous conditions for coupling steps (HATU/HBTU/EDC protocols) to minimize hydrolysis.
    • Monitor reactions by HPLC at 260–320 nm where the naphthyl chromophore absorbs strongly.
    • If chiral integrity is critical, use mild bases (DIPEA, NMM) and avoid prolonged exposure to high pH/temperature to mitigate racemization at Cα.

Reaction Conditions

• General coupling conditions (literature guidance; optimize per system)
  • Solvents: DMF, DCM, NMP, or mixtures; for greener choices, consider NBP or aqueous DMF with surfactants.
  • Bases: DIPEA, NMM; mild conditions help preserve stereochemistry at Cα.
  • Activators: HATU, HBTU, PyBOP, EDC (with HOAt/HOBt or OxymaPure). Typical temperatures: 0–25 °C. Times: 0.5–16 h depending on sterics.
  • Protecting groups: Boc/Fmoc on the α-amine when selectivity is required; benzyl or tert-butyl esters for temporary masking of the γ-CO2H.
• Hydrolysis/derivatization
  • The α-naphthylamide is generally stable to neutral aqueous conditions but can hydrolyze under strong base or acid with heat. If enzymatic studies require intact amide, avoid extremes of pH and elevated temperatures.
• Analytical monitoring
  • HPLC with UV detection at 260–320 nm is effective due to the naphthyl chromophore; MS (ESI) readily detects [M+H]+ around m/z ~303 for C16H18N2O4-type compositions (context only).
• Expected outcomes (examples from analogous systems)
  • Amidations/esterifications of the γ-CO2H with unhindered partners often proceed in 60–90% isolated yield under HATU/DIPEA at rt. Sterically hindered or poorly nucleophilic partners may require gentle heating or longer times.

Safety and Handling

• Item-specific (from Product Data)
  • GHS classification: Not specified for this item; refer to SDS.
  • Signal word: Not specified for this item; refer to SDS.
  • H-statements / Pictograms: Not specified for this item; refer to SDS.
  • Storage conditions: Room temperature.
• General laboratory safety guidance (literature/practice; not a substitute for SDS)
  • Likely hazards: Aromatic amides and naphthalene derivatives may cause skin/eye irritation; dust can be a respiratory irritant. Avoid inhalation and contact.
  • PPE: Lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood when weighing powders or preparing concentrated solutions.
  • Incompatibilities: Strong oxidizers (risk of oxidation of the aromatic moiety), strong acids/bases may hydrolyze the amide under forcing conditions; avoid prolonged exposure to strong oxidants and extremes of pH/heat.
  • First aid (overview):
    • Skin/eye contact: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
    • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
  • Handling tips: Minimize moisture uptake and light exposure to preserve chromophore integrity. Keep container tightly closed; avoid generating dust. Always consult the product SDS for authoritative hazards and response measures.

Solvent Selection

• Compound type and polarity (general)
  • Amphoteric amino acid derivative with one free carboxylic acid, one primary amine, and a hydrophobic 4-methoxynaphthyl amide. Exhibits pH-dependent solubility in water; enhanced solubility in polar aprotic solvents.
• Practical solvent choices (literature/practice)
  • Stock solutions: Anhydrous DMSO or DMF are preferred for preparing concentrated stocks (e.g., 10–100 mM), then dilute into buffered aqueous media while mixing to avoid precipitation.
  • Aqueous systems: Solubility increases at pH > pKa of the carboxyl (formation of carboxylate) and may decrease near the isoelectric point. Adjust pH with minimal base (e.g., NaOH) or acid to achieve dissolution, then back-titrate as required.
  • Alcohols: Methanol/ethanol can assist as co-solvents for analytical sample prep but may affect enzyme assays; validate compatibility.
• Small comparison (general)
  • Water/buffer: Best for biological assays; may require pH adjustment.
  • DMSO: Strong solvating power; low volatility; good for stocks, but limit final v/v% (commonly ≤1–2% in enzyme assays).
  • DMF: Similar to DMSO; consider cytotoxicity and background absorbance in UV.
• Tips
  • Filter or centrifuge after dilution if microprecipitates form.
  • Pre-wet glassware/filters with solvent to minimize adsorption of hydrophobic chromophores.

Storage and Reconstitution

• Item-specific (from Product Data)
  • Storage conditions: Room temperature.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
  • Reconstitution: Not specified for this item; refer to CoA/Spec Sheet.
• General guidance (for this class of compounds)
  • Storage: Keep tightly closed in a dry, room-temperature environment away from direct light. If long-term storage is required, consider desiccation and inert atmosphere to minimize hydrolysis/oxidation of the chromophore.
  • Reconstitution: Prepare concentrated stocks in anhydrous DMSO or DMF (e.g., 10–50 mM). For aqueous use, dilute the organic stock into buffer with vigorous mixing; adjust pH if needed to maintain solubility. Avoid repeated freeze–thaw cycles by aliquoting stocks.
  • Stability: Monitor by HPLC/UV for any degradation over time, especially in basic or strongly acidic media. Follow the lot-specific CoA/SDS for definitive instructions.

Structure and Identity

• Item-specific (from Product Data)
  • Product name: L-Glutamic acid alpha-(4-methoxy-beta-naphthylamide)
  • CAS: 74938-90-2
  • CID: 7015691
  • InChIKey: 162794
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed (for context; not item specifications)
  • Likely gross structure: L-glutamic acid in which the α-carboxyl is converted to an amide with 4-methoxy-2-naphthylamine, leaving the side-chain (γ) carboxyl free and the α-amine intact (L-configuration at Cα).
  • Functional groups: primary amine (α-NH2), carboxylic acid (γ-CO2H), aromatic amide (α-CONH–naphthyl), methoxy-substituted naphthalene chromophore.
  • Stereochemistry: one stereogenic center at Cα, L-configuration (S at the α-carbon under standard amino acid CIP conventions).
  • 2D description in words: An α-amino acid backbone (NH2–CH(R)–CO–NH–Ar) where R = –CH2–CH2–CO2H and Ar = 4-methoxy-2-naphthyl. The α-carboxyl is part of an anilide linkage to the substituted naphthalene; the side-chain terminates in a free acid.

Synthetic Utility

• Functional handles inherent to this molecule (general)
  • Free α-amine: amenable to acylation, carbamate formation, or peptide coupling to yield N-acyl derivatives while retaining the α-CONH–Ar cap.
  • Free γ-carboxylic acid: can be esterified, amidated, or coupled to form γ-glutamyl linkages; useful for constructing peptidomimetics or attaching to solid supports.
  • Aromatic naphthylamide: provides a spectroscopic handle (UV/fluorescence) to monitor transformations and purifications.
• Representative transformations (literature)
  • Coupling at the γ-CO2H with amines/alcohols using EDC/HOBt, HATU/DIPEA, or mixed anhydrides to furnish γ-amides/esters (potential enzyme substrates or conjugates).
  • Selective protection of the α-NH2 (e.g., Boc, Fmoc) to enable orthogonal chemistry at the side chain, followed by deprotection under standard conditions (Boc: acidolysis; Fmoc: base).
  • Activation of the γ-CO2H as NHS esters for bioconjugation to lysine residues on proteins/peptides, providing fluorescent readouts via the naphthyl tag.
• Retrosynthetic value
  • Disconnection at the α-amide suggests assembly from L-glutamic acid (or a protected derivative) and 4-methoxy-2-naphthylamine under peptide-coupling conditions, highlighting modular late-stage diversification.

Target Specificity

• Item-specific
  • No target, antigen, or enzyme specificity is provided for this product. It is supplied as a chemical reagent for research use only.
• Context
  • Naphthylamide-bearing amino acid derivatives are often incorporated into enzyme substrates, but specificity arises from the full substrate structure, not from the amino acid derivative alone. Any target claims must be established by the end user’s design and validation.