8-Deazafolic acid , CAS No.51989-25-4

CAS: 51989-25-4 Cat. No.: D1418077 Summenformel: C₂₀H₂₀N₆O₆ Molekulargewicht: 440.41

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

8-Deazafolic acid is an antimicrobial drug for the folate-dependent bacteria, Streptococcus faecium (ATCC 8043) and Lactobacillus casei (ATCC 74691). 8-Deazafolic acid has activity against lymphoid leukemia L1210 in mice.

Specifications

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Aktionsart

INHIBITOR

Namen und Kennungen

Molekulargewicht

440.41

Application Protocols

No assay protocols are provided in the Product Data. The following general research-only guidance can help initiate work; adjust per your system.

• Stock preparation:
  • Weigh the solid quickly under low light.
  • Dissolve to 10–50 mM in anhydrous DMSO with gentle warming/sonication; protect from light.
  • Filter through 0.22 µm PTFE if particulate is observed.
• Enzyme binding/biochemical assays:
  • Dilute DMSO stock into assay buffer (e.g., 50 mM HEPES, pH 7.5, 100 mM NaCl, 1 mM DTT as needed), keeping final DMSO ≤ 1–2% v/v.
  • Include appropriate controls (vehicle, folic acid as reference) to interpret binding vs activity effects.
• Analytical standardization:
  • Prepare calibration solutions in DMSO:water (1:9) or buffer with small DMSO content.
  • Use amber vials; verify stability over the analytical run by bracketing QC samples.

These are non-binding starting points; consult the literature for system-specific parameters and validate in-house.

Biological Roles

General biochemical context (literature):

• Folates function as carriers of one-carbon units in cellular metabolism, enabling biosynthesis of purines, thymidylate, and certain amino acids via folate-dependent enzymes (e.g., DHFR, TS, SHMT, MTHFR). The active cofactor forms are reduced and polyglutamylated derivatives of folic acid.
• 8-Deazafolic acid modifies the electronic structure of the pteridine ring by replacing N8 with carbon, which can alter redox properties and hydrogen-bonding while maintaining the geometric presentation of the PABA–glutamate moiety.
• As a research tool, 8-deaza analogs help dissect binding interactions in folate transporters and enzymes by isolating contributions of the heteroaromatic ring nitrogen to catalysis versus affinity.
• Transport and cellular handling: Folates interact with reduced folate carriers, folate receptors, and proton-coupled folate transporters; deaza analogs can be used to probe selectivity and transport mechanisms in vitro.

Important notes:

• No medical or clinical claims are made. This product is supplied strictly for laboratory research.
• Biochemical behaviors of 8-deazafolic acid may differ from folic acid in reduction potential and enzymatic turnover; such differences are system- and assay-dependent and should be empirically determined.

Buffer Applications

This compound is not a conventional buffering agent. It contains ionizable groups but is not used to control pH in biochemical or analytical systems.

Practical guidance:

• If preparing solutions for biochemical assays, select an external buffer system appropriate for your enzyme or binding study (e.g., phosphate, HEPES, Tris, or MOPS) and dissolve 8-deazafolic acid in a compatible co-solvent (e.g., DMSO) before dilution into the buffer.
• For solubility, mildly basic buffers (e.g., carbonate, pH ≥ 9) can assist dissolution for preparative purposes; avoid large pH excursions if native-like conditions are required for your assay.

Green Alternatives

Primary environmental footprint here arises from solvent choice in dissolution, purification, and analytics rather than the compound itself. Greener strategies focus on solvent substitution and process minimization.

• Prefer aqueous systems when feasible: If assay tolerance allows, use mildly basic aqueous buffers to dissolve/handle the compound, reducing reliance on dipolar aprotics.
• Replace dipolar aprotics where possible:
  • Instead of DMF/NMP: explore aqueous bicarbonate, ethanol/water co-solvents, or propylene carbonate for certain processing steps.
  • DMSO: although not ideal, it is generally considered lower-toxicity and more biodegradable than DMF/NMP; keep volumes minimal and capture for waste treatment.
• Chromatography: Use volatile, low-toxicity buffers (ammonium bicarbonate/acetate) to enable water-rich mobile phases and facilitate solvent recovery.

Illustrative comparison (general):

• Aqueous basic buffer: renewable, low toxicity; may alter pH-sensitive assays or degrade sensitive motifs with prolonged exposure.
• DMSO: effective solubilizer with acceptable EHS profile; viscous and may complicate waste handling.
• DMF/NMP: strong solvency but higher hazard profiles; avoid when alternatives suffice.

Operational tips:

• Maximize concentration to reduce solvent volume in stocks.
• Use amber glassware to reduce photodegradation, limiting the need for repeat preparations (waste reduction).

Pharmaceutical Uses

No therapeutic or clinical use is claimed. The following describes research/formulation-related roles observed in the literature and in R&D settings.

• Reference/analytical standard: Employed as a comparator or impurity standard in method development for folate-related compounds.
• Tool compound in preformulation: Evaluating transporter binding or enzyme affinity without redox turnover can guide early-stage screening and selectivity assays.
• Conjugation handle for delivery studies: The glutamate carboxylate(s) enable formation of esters or amide linkages to explore folate-receptor-mediated uptake of conjugates in cell models.
• Regulatory status: No pharmacopeial monograph is known for 8-deazafolic acid specifically; verify any compendial requirements for related substances if applicable. Not specified for this item; refer to CoA/Spec Sheet.

Formulation considerations (research only):

• Solubilization via DMSO stocks followed by dilution into isotonic buffers; maintain DMSO ≤ 1–2% v/v in biological media to limit vehicle effects.
• Light protection with amber containers; avoid prolonged exposure to elevated temperatures.

Physical Properties

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

Literature/general guidance (for method development only):

• Physical form: typically a yellow to orange solid for folate analogs; exact appearance for this lot is not specified.
• Acid–base behavior: polyfunctional acid/base with carboxylates (acidic) and an aromatic amine (basic). Zwitterionic around neutral pH; markedly more soluble in basic aqueous media and polar aprotic solvents (e.g., DMSO).
• Solubility trends (literature): sparingly soluble in water at neutral pH; increased solubility in alkaline buffers (e.g., pH > 8) and in DMSO/DMF; poor solubility in nonpolar solvents.
• Stability considerations: sensitive to prolonged light and oxidative conditions, similar to folate derivatives; solutions are best prepared fresh, protected from light, and stored cold.
• UV–Vis features (literature): folate chromophores exhibit characteristic bands near 280 nm and 350 nm depending on pH and conjugation state; exact λmax for 8-deaza variant may shift slightly from folic acid.
• Hygroscopicity: not generally considered strongly hygroscopic, but drying under vacuum is common practice before weighing for analytical work.

Note: Do not treat the above as product specifications; verify experimental parameters empirically and consult the CoA for any required numerical values.

Quality and Grades

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

General guidance on quality considerations for folate analogs:

• Analytical verification: Identity is typically confirmed by 1H/13C NMR, HRMS, and HPLC/UPLC purity. For polyacidic analytes, ion-pair or reversed-phase LC methods are common; UV detection near 280–360 nm is typical due to the conjugated chromophore.
• UV background: When used in analytical or biological assays, low-UV-impurity profiles are desirable to minimize baseline interferences.
• Residual solvents/metals: For sensitive enzymology, low residual metals and low peroxide/oxidants are preferred; verify via CoA if required. Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers: None indicated in Product Data. If stabilizers are present for some lots, they should be disclosed on CoA; confirm before quantitative UV work.
• Batch-to-batch consistency: For SAR or screening libraries, maintain the same lot to ensure reproducibility given potential polymorph/solvate effects in polyfunctional solids.

Recommendation: If assay-critical, request full analytical package (CoA with chromatogram, spectra, water content) specific to the lot you will receive.

Reaction and Applications

Applications (research/manufacturer context): Not provided in Product Data. The following are literature-informed research uses for 8-deaza folate analogs; do not construe as product specifications.

• Enzymology probes: 8-Deazafolic acid mimics folic acid while altering the electronic properties of the pteridine ring, enabling mechanistic studies of folate-dependent enzymes (e.g., dihydrofolate reductase, thymidylate synthase) in binding and turnover assays.
• Spectroscopic standards: The deaza modification can shift UV–Vis features slightly versus folic acid, useful for dissecting contributions of the heteroaromatic ring to spectral signatures.
• Affinity tools: The preserved PABA–glutamate framework allows conjugation (via γ- or α-carboxylate activation) to supports, dyes, or affinity tags for pull-downs of folate-binding proteins and transporters.
• SAR/ligand design: Serves as a reference point in structure–activity studies aimed at decoupling redox chemistry of the pteridine from binding interactions in the folate pocket.

Practical notes:

• Solubility management: Prepare concentrated DMSO stocks; dilute into assay buffers with vigorous mixing to avoid precipitation.
• Light/oxidation: Work under reduced light; minimize air exposure for solutions. Include antioxidant (e.g., ascorbate) only if compatible with the assay.
• Purification: For synthetic derivatives, reversed-phase preparative HPLC with ammonium formate/acetate buffers is commonly used to manage strong polarity and ionization.

Reaction Conditions

General laboratory conditions for derivatizing 8-deazafolic acid (literature-informed; adjust empirically):

• Carboxyl activation and amide coupling:
  • Solvent: DMF or DMSO, sometimes with minimal water; for cleaner workups, use anhydrous conditions.
  • Reagents: EDC·HCl (1.1–1.5 equiv) with NHS (1.2–1.5 equiv) or HATU (1.1–1.3 equiv); base such as DIPEA (2–4 equiv).
  • Temperature/time: 0–25°C, 1–16 h; monitor by RP-HPLC.
  • Workup: Quench with aqueous buffer; purify by preparative RP-HPLC with water/acetonitrile + 0.1% formic or acetic acid (or ammonium acetate for MS).
• Selective esterification of γ-CO2H:
  • Use alcohol (MeOH/EtOH) with acidic catalysts (e.g., HCl in alcohol) at 0–25°C to form monoesters; control is substrate- and condition-dependent.
• Aromatic amine acylation:
  • Reagents: acyl chlorides or activated esters; solvent DCM/DMF mixtures; base pyridine or DIPEA; 0–25°C.

Chromatography and analysis:

• Mobile phases: water/acetonitrile or water/methanol with volatile buffers (ammonium formate/acetate, pH 4–7) to balance peak shape and ionization.
• Detection: UV at 280–360 nm; MS in negative or positive ESI depending on derivatization.

Note: The compound may be light-sensitive; perform reactions under reduced light and protect intermediates with amber glassware.

Safety and Handling

Authoritative safety data for this item are not specified in the Product Data. Always consult the product’s SDS for definitive guidance. The following are general best practices for folate analogs and heteroaromatic polyacids used in research.

• GHS/Classification: Not specified for this item; refer to SDS. In the absence of a classification, handle as a laboratory chemical of unknown hazard.
• Likely hazards (general): May cause irritation to eyes/skin/respiratory tract upon contact with dust. Avoid inhalation of powders and contact with eyes.
• PPE: laboratory coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use dust control measures and handle in a fume hood when weighing or dissolving.
• Storage incompatibilities: Avoid strong oxidizers and strong acids/bases during storage. Light-sensitive; protect solids and solutions from light.
• Handling tips: Prepare solutions under subdued light. Use amber vials/syringes for storage and transfer. Filter sterilize if sterility is required; avoid high temperatures and prolonged exposure to air.
• First aid (overview; defer to SDS): Eye/skin contact—rinse with water for several minutes; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical attention as appropriate.
• Waste: Dispose of according to local regulations for organic laboratory chemicals; avoid drain disposal.

Research use only: This material is provided strictly for laboratory research. No food, drug, cosmetic, or household use.

Solvent Selection

8-Deazafolic acid is a highly polar, polyfunctional molecule with multiple ionizable groups. Practical solvent choices depend strongly on the intended pH and use-case.

• Primary stock solutions (analytical/biochemical):
  • DMSO: often the most reliable for concentrated stocks (e.g., 10–50 mM), followed by dilution into buffer. Warm gently and vortex/sonicate. Protect from light.
  • DMF: alternative to DMSO when lower viscosity is desired; consider moisture control.
• Aqueous media:
  • Neutral pH water/buffer: limited solubility; expect turbidity or precipitation upon direct dissolution from solid.
  • Basic buffers (e.g., carbonate, borate, pH ≥ 9): markedly improved solubility due to carboxylate deprotonation (literature behavior for folates).
  • Acidic buffers: low solubility; avoid for concentrated stocks.
• Alcohols: Methanol/ethanol can assist in co-solvent systems, but complete dissolution may still require DMSO or base.
• Miscibility and polarity: As a charged/zwitterionic analyte, it is incompatible with nonpolar solvents (hexanes, toluene) except as minor components in chromatographic systems.

Comparison (general):

• DMSO vs DMF: DMSO offers broader solubilization but higher viscosity; DMF is easier to pipette but may extract plasticizers—use glassware.
• Aqueous base vs DMSO: Aqueous base avoids organic aprotics but may not be suitable for pH-sensitive assays; DMSO allows neutral-buffer dilutions if kept below 1–2% v/v in the final assay.

Tip: Filter warm solutions through 0.22 µm PTFE/nylon to remove particulates before analytical injections.

Storage and Reconstitution

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

• Storage Conditions: Store at -20°C.
• Shipped In: Ice chest + Ice pads.
• Research Use Note: For research use only.

General storage guidance:

• Solid: Keep tightly capped in original amber container at -20°C, protected from light and moisture. Allow vial to warm to room temperature in a desiccator before opening to reduce condensation.
• Solutions: For short-term use, store aliquots at -20°C (or 4°C for very short periods) in amber vials, under inert atmosphere if possible. Avoid repeated freeze–thaw cycles; prepare single-use aliquots.

Reconstitution suggestions (research only):

• Prepare concentrated stocks in anhydrous DMSO (e.g., 10–50 mM). Vortex/sonicate and warm gently (≤40°C) to aid dissolution. Alternatively, dissolve in minimal 0.1 M Na2CO3, then adjust to desired buffer conditions.
• Upon dilution into aqueous buffers, add slowly with vigorous mixing to minimize precipitation. If necessary, include a modest co-solvent fraction (≤2% DMSO) in the final solution.
• Always protect from light during preparation and storage (foil wrap or amber ware).

Stability notes:

• Exact shelf-life and solution stability are not specified for this item; refer to CoA/Spec Sheet and verify experimentally by HPLC/UV before critical use.

Structure and Identity

Overview: 8-Deazafolic acid is a deaza analog of folic acid in which the N at the 8-position of the pteridine (pterin) ring is replaced by carbon. It retains the classical folate triad: pteridine-like heteroaromatic, p-aminobenzoate (PABA) spacer, and L-glutamate tail.

Item-specific identifiers from Product Data:

• CAS: 51989-25-4
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• 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/structural description (general, non-spec):

• Common name: 8-Deazafolic acid (8-deaza analog of folic acid)
• Structural features: heteroaromatic bicyclic “pteridine-like” system fused to an anilide (p-aminobenzoate), amide linkage to L-glutamate bearing α- and γ-carboxylates.
• Functional groups: heteroaromatic ring system, anilide, primary aromatic amino (para to amide), one or more amide bonds, dicarboxylic acid (glutamate), potential zwitterionic character depending on pH.
• Stereochemistry: one chiral center at the α-carbon of L-glutamate (L-configuration, literature).
• 2D structure (described): a bicyclic aromatic core (deazapteridine) attached at C-6 to a para-aminobenzoate; the benzoate is amide-coupled through its carboxylate to the α-amino of L-glutamic acid; the glutamate γ-carboxylate remains free (diacid).

Synthetic Utility

As a functionalized folate analog, 8-deazafolic acid serves more as a ligand/probe framework than as a general building block. Nonetheless, several synthetic manipulations are practical in a research context:

• Carboxylate derivatization: Activation of the γ- (and/or α-) carboxylate of the glutamate tail allows amide coupling to labels, linkers, and solid supports (EDC/HOBt, HATU, or carbonyldiimidazole methods). Selectivity strategies may involve temporary esterification of one carboxylate.
• Aromatic amine modification: The para-amine on the PABA moiety can be acylated, sulfonylated, or diazotized (with care) to generate reporter-bearing derivatives while largely preserving the folate recognition motif.
• Heteroaromatic core functionalization: The 8-deaza pteridine-like ring is less nucleophilic at N8 (now C) and may exhibit altered reactivity toward electrophiles vs folic acid; direct core functionalization typically requires protecting-group strategies and carefully chosen electrophiles.
• Conjugation chemistry: NHS esters or active carbonates derived from the carboxylates enable bioconjugation to amines on peptides/proteins for receptor-targeting studies.

Analytical development:

• The chromophore facilitates UV monitoring during coupling/purification (RP-HPLC). Buffer systems with volatile ammonium salts aid MS compatibility.

Target Specificity

No antibody or biologic targeting information is applicable to this small-molecule folate analog. Target specificity data (clone, isotype, species reactivity, etc.) are not relevant to this product type.

Häufig gestellte Fragen

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 51989-25-4, the molecular formula is C20H20N6O6, and the molecular weight is 440.41 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.