GRADE & PURITYMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.
This compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
External Descriptors
nucleoside triphosphate analogue
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.
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Application Protocols
Item-specific (from Product Data)
No tested applications, recommended dilutions, or validated protocols are provided.
Statement
Not specified for this item; refer to CoA/Spec Sheet. For general handling in biochemical assays, see the Reaction Conditions and Buffer Applications sections for literature-based guidance to design and optimize your own protocols.
Biological Roles
General biochemical context (literature; not item-specific claims)
ATP is the universal energy currency and a signaling molecule via P2X (ligand-gated ion channels) and P2Y (GPCR) receptors. β,γ-methylene ATP analogs are designed to resist hydrolysis at the β–γ bond, influencing their interactions with ATP-binding proteins and purinergic receptors.
L-βγ-meATP specifically features the L-ribose stereochemistry, which is rare in nature. Many ATP-binding proteins are stereoselective for the D-ribose configuration; consequently, L-analogs often display diminished binding or activity, making them valuable as negative controls or to probe stereochemical constraints.
In enzymology, nonhydrolyzable analogs can stabilize pre-catalytic conformations, allowing interrogation of binding events decoupled from phosphate transfer. The L-form further reduces unintended catalytic turnover by mismatching natural chirality.
In receptor pharmacology, β,γ-methylene ATP analogs have been used to study P2X/P2Y selectivity and desensitization kinetics. Activity of the L-form should be empirically determined, as potency can vary by receptor subtype and species.
Experimental considerations
Complexation with Mg2+ frequently modulates affinity/efficacy for ATP-dependent targets; define Mg2+ concentration in assays.
Nonspecific degradation (e.g., by phosphatases) can occur at terminal phosphates or via metal-catalyzed pathways; maintain clean, nuclease-/phosphatase-minimized conditions.
Employ matched controls (ATP, D-βγ-meATP, AMP-PNP) to parse binding vs hydrolysis and stereochemical effects.
Buffer Applications
Applicability
As a highly polar nucleotide analog, L-βγ-meATP is typically handled in aqueous buffers for biochemical and receptor/pharmacology assays. No classical “buffering” role is expected; instead, the compound is a buffered-solute component.
Practical buffer guidance (literature/general)
Stock solutions: 10–100 mM in nuclease-free water or buffer, pH 7.0–7.4. Adjust pH with NaOH/KOH if supplied as the free acid. Filter-sterilize (0.22 µm) if needed.
Assay buffers: HEPES (10–50 mM), Tris (20–50 mM), or phosphate-buffered saline; ionic strength 100–150 mM NaCl is common for protein targets. Add MgCl2 (0.5–5 mM) when mimicking MgATP binding states.
Stability considerations: Avoid pH <5 or >9 and elevated temperatures to limit phosphate migration/decomposition. Store working solutions cold and protected from microbial contamination.
Electrophysiology: For P2 receptor studies, prepare extracellular-like solutions (e.g., 10 mM HEPES, 140 mM NaCl, 2.5 mM KCl, 2 mM CaCl2, 1 mM MgCl2, pH 7.3–7.4). Verify activity of the L-form in your system.
Notes
Do not mix with strong chelators if Mg2+-dependent binding is required; conversely, include EDTA (0.1–1 mM) to suppress metal-catalyzed breakdown when Mg2+ is not needed.
Always confirm concentration via UV at 259–260 nm using an extinction coefficient appropriate for the specific salt/form (literature value; verify experimentally).
Green Alternatives
Context
For this highly polar nucleotide analog, environmental considerations revolve around aqueous media choice, minimizing hazardous additives, and waste reduction rather than solvent substitution in organic synthesis.
Greener practice recommendations (general guidance)
Use water-based buffers (HEPES, phosphate, TRIS) instead of organic cosolvents wherever possible.
Avoid chlorinated solvents entirely; they offer no solubility advantage for triphosphates and increase environmental burden.
Employ microplate-based screening to reduce reagent consumption (µL scale) and waste volume.
Buffer selection: choose zwitterionic buffers with benign ecotoxic profiles (e.g., HEPES) and avoid excessive concentrations of heavy metal cofactors.
Sterilization/clarification: prefer membrane filtration over azide preservatives when compatible with the assay to reduce hazardous waste.
Environmental impact: lower for purely aqueous systems.
Performance: better stability for polyphosphates in neat aqueous buffers at neutral pH; DMSO unnecessary in most nucleotide assays.
End-of-life
Collect phosphate-rich solutions separately if local regulations require; neutralize and dispose per institutional guidelines. Avoid mixing with halogenated solvent waste streams.
Pharmaceutical Uses
Item-specific
No pharmacopeial status, excipient role, or manufacturing-grade details are provided for this item. Refer to CoA/Spec Sheet for any regulatory notes.
Literature/General, non-clinical context
Reference standard/control: Nonhydrolyzable nucleotides and stereochemical analogs (e.g., L-forms) are used as analytical reference materials in method development (HPLC/LC–MS), impurity profiling, and as controls in biochemical assays supporting discovery workflows.
Formulation science (research only): Nucleotide analogs can be incorporated into in vitro assay kits, lyophilized reagent pellets, or screening plates as positive/negative controls. Their high polarity typically necessitates aqueous formulations with stabilizing counterions and controlled pH.
Manufacturing process development: May serve as a model substrate analog to study ATP-dependent steps in biocatalytic processes without turnover, informing process parameters and enzyme selection.
Caveats
No therapeutic or clinical claims are made for this product. It is designated For research use only (per Product Data) and is not intended for human or animal use in vivo or for diagnostic procedures.
Physical Properties
Item-specific specifications
Appearance: 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.
Water content, residual solvents, metals, UV cutoff, RI, pKa: Not specified for this item; refer to CoA/Spec Sheet.
Literature/General properties for β,γ-methylene ATP analogs (context only)
Aggregation/state: typically provided as a solid (often as an alkali metal salt) or lyophilized powder; highly hygroscopic behavior is common for polyphosphates.
Solubility: high in water and aqueous buffers; negligible in aprotic organic solvents. Typical working stocks are 1–100 mM in water, PBS, or HEPES-based buffers (pH ~6.8–8.0), often with Mg2+ present.
pKa (phosphate groups, literature): multiprotic; apparent pKa values for triphosphates span roughly 1–7 across ionizations; exact values depend on ionic strength and counterions.
LogP: strongly negative (highly anionic); effectively non-partitioning into nonpolar media.
Thermal behavior: nucleotides decompose before boiling; thermal sensitivity increases with moisture and pH extremes.
Notes
The L-stereochemistry is expected to minimally affect bulk physicochemical properties (e.g., solubility) but can profoundly change biological recognition.
For any quantitative use (e.g., exact MW for solution prep), consult the item-specific CoA to retrieve the precise counterion form and formula.
Quality & Grades
Item-specific
Grade: Moligand™
Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Counterions: Not specified for this item; refer to CoA/Spec Sheet.
What Moligand™ typically implies (general information)
Screening-grade small-molecule/ligand library standard: Emphasis on identity confirmation, suitability for biochemical/target screening, and batch traceability.
QC elements commonly associated with ligand-library materials include identity verification by orthogonal methods (e.g., MS, NMR), assessment of gross purity sufficient for screening tiers, and documentation suitable for hit validation workflows. Exact tests and acceptance criteria are item-specific and provided on the CoA.
Practical implications for users
Verify the counterion/salt form on the CoA to calculate exact working concentrations (mM). Triphosphates may be supplied as alkali salts; the number of counter-cations affects formula weight.
UV background and inorganic impurities can impact spectrophotometric assays; if using absorbance at 259–260 nm to quantify, rely on an extinction coefficient appropriate to the exact salt/form and correct for ionic strength.
If your application requires analytical- or bioUltra-grade specifications (e.g., endotoxin limits, metal ion limits, or very low UV background), consult with Technical Support for the availability of tighter grades, or purify in-house (e.g., desalting, HPLC) as needed.
Documentation
For acceptance criteria, analytical methods, and batch-specific results, refer exclusively to the item’s CoA/Spec Sheet.
Reaction & Applications
Scope (general, literature-based; expand as applicable to ligand-screening use)
Biochemical probing: L-βγ-meATP serves as a nonhydrolyzable ATP analog with the β–γ bridging oxygen replaced by –CH2–, reducing susceptibility to enzymatic cleavage at that bond. The L-ribose configuration typically diminishes interaction with ATP-binding proteins relative to D-analogs, supporting its use as a stereochemical control or negative comparator in target validation.
Purinergic receptor studies: β,γ-methylene ATP analogs are established ligands for P2X/P2Y receptor families. The L-form may exhibit markedly altered potency/efficacy; it can be used to differentiate stereochemical requirements in binding assays and electrophysiology (literature context).
Enzyme assays: Investigations of kinases, ATPases, and motor proteins where prevention of γ-phosphate transfer is desired at the β–γ junction. Residual hydrolysis at other positions or by nonspecific phosphatases should still be considered.
Structural biology: Useful in stabilizing ATP-bound conformations without turnover for cryo-EM or crystallography, often in presence of Mg2+ and protein of interest; the L-form can minimize native binding, helping to assess nonspecific interactions.
Practical considerations
Prepare fresh aqueous stocks; maintain pH near neutrality. Include Mg2+ to mimic physiological complexes if the target requires MgATP.
Validate functional activity in your specific system; L-stereochemistry can lead to weak or negligible activity at many ATP-binding sites.
Control experiments: Compare against ATP, D-βγ-meATP, or non-hydrolyzable analogs (e.g., AMP-PNP) to interpret binding vs turnover effects.
Reaction Conditions
Scope
This section summarizes typical assay/experiment conditions for ATP analogs like L-βγ-meATP. Values are literature-based general guidance and must be optimized per target.
Typical conditions
Stock preparation: 10–100 mM in water or buffer, pH 7.0–7.4; filter-sterilize. Store aliquots to minimize freeze–thaw.
Binding/enzymology assays:
Buffer: 20–50 mM HEPES or Tris, 100–150 mM NaCl, pH 7.2–7.6.
Cofactor: 0.5–5 mM MgCl2 where MgATP is physiologically relevant; omit or reduce Mg2+ if it promotes unwanted interactions.
Temperature: 4–25°C for binding; up to 30°C possible with monitoring for stability.
Concentration range: 0.1 µM to 1 mM depending on target affinity; perform titrations to determine KD or functional EC50/IC50 (if any).
Electrophysiology (P2 receptors):
External solution: ~10 mM HEPES, 140 mM NaCl, 2.5 mM KCl, 2 mM CaCl2, 1 mM MgCl2, pH 7.3–7.4.
Application: rapid perfusion; start at 1–100 µM and adjust based on response. The L-form may have reduced efficacy.
Structural biology:
Incubate protein with 1–10 mM L-βγ-meATP plus Mg2+ and any required co-ligands before grid prep/crystallization.
Controls
Include ATP, D-βγ-meATP, and/or AMP-PNP to benchmark binding vs hydrolysis and stereochemical dependencies.
Note
These are literature-style conditions, not item-specific specifications. Optimize empirically for your system.
Safety & Handling
Item-specific hazard information (from Product Data)
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
Hazard (H) statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General laboratory safety guidance (literature/standard practice)
Expected hazards: Nucleotides are generally of low acute toxicity but may cause irritation to eyes, skin, or respiratory tract as dust or solution.
PPE: lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Avoid inhalation of powders; handle in a clean area or fume hood if aerosol/dust may form.
Incompatibilities: Strong acids/bases (hydrolysis), strong oxidizers, and enzymes (apyrases/ATPases) which can degrade nucleotide stocks (less so at the β–γ linkage here, but terminal phosphates remain susceptible to metal-catalyzed breakdown).
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin contact: wash with soap and water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; remove contact lenses if easy; seek attention if irritation continues.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Handling tips: Use clean, nuclease-free water/buffers. Minimize repeated freeze–thaw of aqueous stocks. Protect from microbial contamination (filter-sterilize and store appropriately). Avoid prolonged exposure to elevated temperatures.
Always consult the product’s SDS for authoritative safety, spill, and disposal guidance.
Solvent Selection
Applicability
L-βγ-meATP is a highly polar, poly-anionic nucleotide analog; selection focuses on aqueous systems rather than organic solvents.
General solvent behavior (literature)
Polarity class: strongly polar/ionic; practically insoluble in aprotic organics (e.g., DCM, Et2O, hexanes) and only sparingly soluble in alcohols.
Preferred media: ultrapure water, physiological buffers (HEPES, Tris, phosphate-buffered saline), and assay buffers with controlled pH (typically 6.8–8.0).
Counterion effects: Solubility and pH of stock solutions depend on the salt form (e.g., Na+, K+). Free acids may require neutralization with NaOH/KOH to reach high concentrations.
Additives: Mg2+ often included (0.5–5 mM) in ATP-sensitive enzyme assays; chelators (EDTA) can modulate metal-catalyzed degradation.
When to choose vs alternatives
Choose L-βγ-meATP when a nonhydrolyzable β–γ linkage is desired to limit hydrolysis at that position and when the L-ribose stereochemistry is required (e.g., as a stereochemical control vs D-βγ-meATP or native ATP).
Alternatives:
D-βγ-meATP: similar nonhydrolyzable analog with natural D-ribose stereochemistry; typically higher biological recognition.
ATP (MgATP): fully native substrate; hydrolyzable at β–γ.
α,β-methylene ATP (α,β-meATP): methylene substitution at α–β; different receptor/enzymatic profiles.
Practical tips
Prepare concentrated stocks (e.g., 10–100 mM) in nuclease-free water or buffer; adjust pH to ~7.0–7.4 if needed. Filter-sterilize through 0.22 µm for cell-free biochemical assays.
Storage & Reconstitution
Item-specific (from Product Data)
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature; complement to item-specific info)
Solid form: Keep tightly closed in the original container, protected from moisture and light. Desiccation is recommended for hygroscopic polyphosphates. If long-term storage is planned, many users store nucleotides at 2–8°C as a precaution, but follow the item label and CoA.
Reconstitution: Use nuclease-/pyrogen-free water or buffer. Typical stock concentrations are 10–100 mM; adjust pH to 7.0–7.4 if necessary (counterion-dependent). Filter-sterilize (0.22 µm) for sensitive assays.
Aliquoting: Prepare single-use aliquots to avoid repeated freeze–thaw. Aqueous aliquots are commonly stored at −20°C or −80°C for extended periods; verify stability for your application.
Compatibility: Include Mg2+ only if required by the target; otherwise, store without divalent cations to limit precipitation or unintended interactions.
Notes
Always consult the batch-specific CoA/SDS for definitive storage and stability details. This product is designated For research use only.
Structure & Identity
Item-specific (from Product Data)
Product name: L-βγ-meATP (SKU: L611466)
CAS: L611466 (catalog identifier; not a standard CAS Registry Number)
PubChem CID: 91532
InChIKey: 358942
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Grade: Moligand™
Literature/General structural description (for context; not item specification)
Common name expansion: L-β,γ-methyleneadenosine 5′-triphosphate (L-β,γ-meATP) is an ATP analog in which the β–γ bridging oxygen is replaced by a methylene (–CH2–) group, and the ribose is the L-enantiomer (mirror image of the naturally occurring D-ribose nucleoside).
Core features: purine adenine base (6-aminopurine) N9-glycosidically linked to L-ribofuranose; 5′-O-triphosphate chain with a β–CH2–γ non-hydrolyzable linkage.
Typical molecular formula (literature, for the neutral free acid): approximately C11H18N5O12P3 (ATP is C10H16N5O13P3; β,γ-CH2 adds C1H2 and removes one O).
Adenine base attached at N9 to the anomeric carbon (C1′) of L-ribose.
The sugar bears a triphosphate at the 5′-oxygen; the terminal (γ) phosphate is connected to the β phosphate via –CH2– rather than an oxygen bridge, making the β–γ bond resistant to hydrolysis.
Stereochemistry: sugar ring is the L-configuration; anomeric configuration typically β at the glycosidic bond.
Synthetic Utility
Applicability
L-βγ-meATP is primarily a biochemical probe rather than a synthetic building block in classical organic synthesis.
Literature/General utility
Mechanistic enzymology: Functions as a nonhydrolyzable ATP surrogate to interrogate binding events in ATP-dependent enzymes (kinases, ATPases, chaperones) without progressing through γ-phosphate transfer. The L-ribose configuration further limits catalytic competence, helping isolate binding phenomena.
Structural stabilization: Used to lock proteins in ATP-bound-like conformations for structural studies (cryo-EM/X-ray), often in complex with Mg2+ and other cofactors. The β–CH2–γ substitution increases resistance to cleavage at that junction.
Selectivity probing: Contrasting L- vs D-analogs informs stereochemical stringency of nucleotide recognition sites; valuable in receptor pharmacology (P2X/P2Y) and nucleotide-binding domain (NBD) analyses.
Not typically applicable
The compound is not generally employed as a reagent for C–C/C–X bond formation, cross-coupling, or protecting-group chemistry. For such purposes, refer to conventional reagents and solvents.
Practical notes
Ensure accurate concentration determination due to salt form variability. Control Mg2+ and pH to match target protein requirements. Consider desalting (spin columns) to exchange buffers before sensitive biophysical measurements.
Target Specificity
Item-specific (from Product Data)
No target specificity, antigen, clone, isotype, or species reactivity information is provided for this product.
Statement
Not specified for this item; refer to CoA/Spec Sheet or contact Technical Support if this material is part of a targeted screening set with defined primary targets.
Need help choosing the grade?
Our grade selection guide covers purity, stabilizer status, and application suitability for all variants in our catalog.
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