Adenosine:H20-C , CAS No.A1448011

CAS: A1448011 Cat. No.: A1448011 Fórmula: C₉₁₃CH₁₅N₅O₅ Peso molecular: 286.25

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

Adenosine:H20- 13 C is the 13 C labeled Adenosine:H20.

Specifications

Condições de armazenamento de armazenamento

Store at -20°C

Enviado em

Ice chest + Ice pads

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

Nomes e identificadores

Peso molecular

286.25

Application Protocols

Item-specific tested applications, recommended dilutions, and controls: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for common laboratory uses (literature/practice-based):

• Preparation of stock solutions:
  • Aqueous: dissolve to 10–100 mM in water or appropriate buffer (pH 7–8) with gentle warming and vortexing; filter through 0.22 μm for enzyme assays.
  • DMSO: prepare concentrated stocks (e.g., 100–500 mM) when higher solubility is required; dilute into assay buffer keeping final DMSO ≤1–2% v/v unless your system tolerates more.
• Spectrophotometric quantification: use absorbance at ~260 nm (literature) with an appropriate extinction coefficient specific to the solvent and pH; validate against a standard curve for your instrument.
• Enzyme assays (e.g., adenosine deaminase): run in phosphate or HEPES buffer at neutral pH; monitor disappearance of adenosine or formation of inosine by HPLC or UV.
• Sample handling for LC/LC–MS: avoid prolonged exposure to strong acids/bases; store autosampler vials at 4–8°C and minimize dwell time to prevent degradation.

These are general recommendations; optimize conditions for your specific system and refer to the item’s CoA for purity/identity confirmation.

Biological Roles

General/literature context for adenosine in biochemistry (no medical claims):

• Metabolic core: adenosine is the ribonucleoside precursor of adenine nucleotides (AMP, ADP, ATP) that mediate cellular energy transfer and serve as cofactors in numerous enzymatic processes.
• Signaling: extracellular adenosine modulates purinergic signaling via P1 receptors (A1, A2A, A2B, A3) influencing second messenger systems such as cAMP; intracellularly, adenosine contributes to nucleotide balance and RNA metabolism.
• Nucleic acids: adenosine is incorporated as adenosine monophosphate (A) into RNA; chemical modifications at the 2′ position or N6 (e.g., m6A) are important epitranscriptomic marks studied with synthetic adenosine analogs.
• Enzymatic pathways: formed by hydrolysis of AMP (5′-nucleotidases) and degraded by adenosine deaminase to inosine; salvaged by adenosine kinase to AMP. These enzymes are widely used in biochemical assays and pathway reconstitution studies.
• Analytical utility: strong absorbance near 260 nm enables spectrophotometric quantification and serves as an internal or external standard in chromatographic methods for nucleosides.

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

Note: All uses are for research and laboratory purposes only as per Product Data (For research use only).

Buffer Applications

Suitability: Adenosine itself is not a buffering agent. It does not constitute a conventional buffer system with a defined pKa/pH working range for maintaining solution pH.

Practical laboratory relevance (general/literature):

• Assay component: adenosine is frequently included as a substrate or standard within buffered systems (e.g., phosphate, Tris, HEPES) for enzyme assays (adenosine deaminase, kinases). The buffer controls pH; adenosine is the analyte/substrate.
• Stock preparation: prepare aqueous stocks in the assay buffer (commonly pH 7.0–8.0) or dissolve in DMSO and dilute into buffer. Filter-sterilize if required for cell-free enzymatic work.
• Compatibility: avoid strong basic buffers that could promote glycosidic hydrolysis over prolonged storage; maintain neutral pH for stability.

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

For maintaining pH, select an appropriate buffer (e.g., phosphate pH 6–8, HEPES pH 6.8–8.2, Tris pH 7–9) based on your enzyme or reaction system; adenosine does not replace these components.

Green Alternatives

When handling nucleosides like adenosine, solvent and reagent selection dominate environmental impact. Consider the following greener choices (literature/general guidance):

• Solvent substitution:
  • Replace DMF with safer polar aprotics where feasible (e.g., dimethyl carbonate, propylene carbonate, Cyrene). Note: solubility and reaction rates for phosphorylation/acylation may differ; pilot trials recommended.
  • Favor water or aqueous ethanol for purification and crystallization where possible.
  • Use ethanol or isopropanol over methanol for precipitations when compatible (lower toxicity).
• Energy efficiency:
  • Conduct dissolutions at ambient temperature with sonication before resorting to heating; consider microwave assistance for specific steps to reduce time.
• Reagent choices:
  • Enzymatic phosphorylation/derivatization (kinases, nucleoside phosphorylases) in aqueous media can reduce reliance on hazardous chlorophosphates and dehydrating agents.
• Waste minimization:
  • Implement miniaturized screening for protecting-group strategies to reduce solvent/reagent volumes.

Comparison snapshot (general):

• DMF vs Cyrene: Cyrene offers lower toxicity and improved biodegradability but may have higher viscosity and limited availability; nucleoside solubility acceptable for some reactions but not all.
• DMSO vs water: DMSO provides superior solubility; water is greener but may suppress moisture-sensitive reactions. Mixed aqueous–DMSO systems can balance both.

Item-specific green metrics (E-factor, solvent guidance): Not specified for this item; refer to CoA/Spec Sheet.

Pharmaceutical Uses

Scope of this section: Formulation/excipient and manufacturing context only. No therapeutic claims.

General/literature context:

• Adenosine is primarily known as a bioactive nucleoside; it is not commonly employed as an excipient. In pharmaceutical research and QC, adenosine can serve as a reference standard for analytical method development (e.g., HPLC assay of nucleosides) and as a process control material in bioprocess analytics.
• In biomanufacturing analytics, nucleosides (including adenosine) are used as system suitability standards for chromatographic systems monitoring nucleotide/nucleoside impurities and degradation products.
• Stabilization and compatibility: when included as a reference material in aqueous formulations, maintain neutral pH and minimize exposure to strong oxidants to prevent degradation.

Item-specific pharmacopeial status, excipient grade, and specifications: Not specified for this item; refer to CoA/Spec Sheet.

Regulatory note: This product is for research use only per Product Data and is not intended for human or animal use in drug products or diagnostics.

Physical Properties

Item-specific physical properties (BP, MP, density, solubility, logP, pKa, refractive index): Not specified for this item; refer to CoA/Spec Sheet.

General/literature characteristics for adenosine (for context only):

• Physical state: typically a white to off-white crystalline solid (literature).
• Thermal behavior: nonvolatile; decomposes before boiling; high melting or decomposition range typical of nucleosides (literature).
• Polarity/solubility: polar and hydrogen-bonding; soluble in water and aqueous buffers to varying degrees depending on pH and ionic strength; increased solubility in polar aprotic solvents (DMSO, DMF, formamide) (literature).
• Acid–base: weakly basic at the exocyclic amine; nucleoside hydroxyls are not appreciably acidic in water (literature).
• UV absorbance: purine chromophore with strong absorbance around 259–260 nm (literature), useful for spectrophotometric quantification in biochemical assays.

Practical notes:

• Hygroscopicity/solvate formation: many nucleosides can retain bound water or form hydrates; drying under high vacuum at mild temperatures may be used when anhydrous material is required (general guidance).
• Solution preparation: prepare aqueous or DMSO stock solutions using gentle warming and sonication if needed; filter-sterilize (0.22 μm) for enzymatic assays to remove particulates.

Always defer to the item’s CoA/SDS for definitive physical property limits for this SKU.

Quality and Grades

Item-specific grade/purity, stabilizers, and analytical specifications: Not specified for this item; refer to CoA/Spec Sheet.

General guidance on grades relevant to nucleosides:

• Research grade: typically suitable for biochemical assays, enzymology, and synthetic transformations, with QC by NMR, HPLC/UPLC, and UV purity at 260 nm. Trace water/solvent content may be reported by Karl Fischer and residual solvent testing (literature practice). Not for clinical use.
• HPLC/LC–MS grade materials (when specified): emphasize low UV background and low non-volatile residues, beneficial for analytical workflows and oligonucleotide synthesis quality control.
• Biochemical/Enzymology grade (when specified): may include tighter control of inorganic ions and heavy metals that can inhibit enzymes; often accompanied by activity-interference testing.

What to check on the CoA for this SKU:

• Identity confirmation: 1H/13C NMR, HRMS, and chromatographic purity trace (e.g., HPLC at 260 nm), water content, and specific counter-ions or hydrates.
• Residual solvents and inorganic impurities: important for sensitive enzymatic or polymerase reactions.
• Lot-specific notes: hydrate state, polymorph, or particle size, which can influence solubility and handling.

If your application requires defined purity thresholds (e.g., ≥98% HPLC, metal limits, endotoxin/bioburden), please verify against the item-specific CoA before use.

Reaction and Applications

Manufacturer applications: Not specified for this item; refer to CoA/Spec Sheet.

General/literature applications for adenosine in research and synthesis:

• Biochemical substrate/standard: used as a reference compound for UV-quantified assays at 260 nm, enzyme kinetics (e.g., adenosine deaminase), and calibration of HPLC methods for nucleosides.
• Phosphorylation chemistry: conversion to 5′-monophosphate (AMP), 5′-diphosphate (ADP), or 5′-triphosphate (ATP) via chemical methods (e.g., POCl3 activation, phosphoromorpholidates, or Ludwig–Eckstein procedures) or enzymatic kinase cascades.
• Protecting-group chemistry: per-silylation (e.g., TMS, TBDMS) to mask 2′/3′/5′-OH groups, enabling selective transformations; N6 acylation or alkylation for base modification.
• Glycosylation/assembly: adenosine is the ribosylated form of adenine; in synthesis, protected adenine is coupled to protected ribose via Vorbrüggen-type glycosylation to form the nucleoside framework.
• Derivatization for probes: introduction of 2′-azido, 2′-fluoro, or 8-substitutions to tune biochemical properties; conjugation handles (e.g., amine linkers at 5′ via phosphoramidites) for immobilization or labeling.

Practical tips:

• Moisture control is critical in phosphorylation and amidite chemistry; dry solvents and glassware.
• Monitor reactions by HPLC at 260 nm and TLC with UV254 plates; nucleosides often show strong UV response.
• Workups: avoid strong base/acid that can cleave the N9-glycosidic bond or cause ribose isomerization; employ buffered aqueous extractions.

Reaction Conditions

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

General/literature guidance for common adenosine transformations:

• Per-silylation (to enable selective acylation/activation): HMDS or BSA with catalytic TMSCl, refluxing in anhydrous acetonitrile or DMF; exclude moisture. Typical times: 2–6 h depending on scale and solvent.
• 5′-Phosphorylation (Ludwig–Eckstein-type): activation with POCl3 in trimethyl phosphate or in DMF, followed by pyrophosphate trapping to form 5′-triphosphates; strict anhydrous conditions at 0–25°C; rapid quench into buffered media to avoid hydrolysis (literature).
• 5′-Phosphoramidite formation: conversion of 5′-OH to 2-cyanoethyl N,N-diisopropyl phosphoramidite using chlorophosphoramidite in dry DCM/DMF with DIPEA at 0–25°C; protect 2′/3′ with silyl groups (literature).
• N6-acylation: acyl chlorides/anhydrides (e.g., benzoylation) in pyridine or DMF at 0–25°C; base protection patterns influence regioselectivity.
• 2′-Modifications: activation via sulfonates (e.g., 2′-O-tosyl on suitably protected nucleosides) followed by substitution (F−, N3−) in polar aprotic solvents at 0–80°C (literature).
• Enzymatic routes: adenosine kinase for AMP formation; nucleoside phosphorylases for transglycosylation under aqueous buffered conditions (pH 6–8, 25–50°C), often with equilibrium control via phosphate concentration.

Always confirm compatibility of solvents/bases/acids with the glycosidic bond and purine stability; monitor by HPLC at 260 nm.

Safety and Handling

Item-specific GHS classification, signal word, hazard statements, and pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance (non-authoritative; follow your institutional EHS and SDS):

• Personal protective equipment: lab coat, safety glasses, and appropriate chemical-resistant gloves. Avoid inhalation of dust and contact with skin/eyes. Use in a fume hood when handling powders or preparing concentrated solutions.
• Incompatibilities: strong oxidizers may degrade nucleosides; strong acids/bases can hydrolyze the glycosidic bond or promote sugar/base modifications. Avoid elevated temperatures that can cause decomposition.
• First aid overview: in case of skin/eye contact, rinse with copious water for at least 15 minutes. If inhaled, move to fresh air; if ingested, rinse mouth. Seek medical attention according to SDS guidance.
• Spill/cleanup: avoid aerosolization; sweep/collect solid carefully; wipe area with water/compatible solvent and dispose of waste per local regulations.
• Fire safety: organic solids are combustible; use water spray, CO2, dry chemical, or foam as appropriate. Combustion may produce nitrogen oxides and carbon oxides.
• Special risks: none specific provided for this SKU. Nucleosides are generally of low volatility but may present dust hazards; minimize dust formation.

Storage per Product Data:

• Store at −20°C. Keep tightly closed in the original container. Protect from moisture and prolonged exposure to light. Shipments: Ice chest + ice pads (as provided). Always consult the SDS for authoritative safety information.

Solvent Selection

Applicability: Adenosine and related nucleosides are polar, hydrogen-bonding molecules; solvent choice strongly affects solubility, reaction efficiency, and analytical detection.

General/literature guidance:

• Aqueous systems: water and buffered solutions (pH 6–8) are typical for biochemical assays and enzymatic conversions. Heating gently (≤40–50°C) and adjusting ionic strength can aid dissolution.
• Polar aprotic solvents: DMSO, DMF, and formamide offer high solubilizing power for stock solutions and for chemical transformations (e.g., phosphorylation, acylation). DMSO is often preferred for biological stock solutions due to miscibility with water and relative inertness.
• Alcohols: methanol and ethanol can dissolve nucleosides to a moderate extent and are frequently used in chromatography mobile phases.
• Nonpolar solvents: generally poor solubility; use only when nucleoside is protected (e.g., per-silylated forms) to increase organic solubility.

Selection tips:

• For biochemical assays: prepare concentrated stocks in water or DMSO, then dilute into buffer; final DMSO ≤1–2% v/v is commonly tolerated by many enzymes (check your specific system).
• For synthetic steps requiring anhydrous conditions: use dry DMF, DMSO, or acetonitrile with molecular sieves; water suppresses many activation chemistries.
• Analytical considerations: UV detection at 260 nm is standard; ensure solvent cutoffs do not interfere.

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

Storage and Reconstitution

Item-specific storage conditions (from Product Data):

• Store at −20°C.
• Shipped in ice chest + ice pads.
• Research Use Only.

General handling and reconstitution guidance for nucleosides:

• Upon receipt: allow the sealed container to equilibrate to room temperature before opening to minimize moisture condensation. Open quickly in a low-humidity environment and reseal promptly.
• Aliquoting: if repeated use is anticipated, prepare single-use aliquots of solid (under dry atmosphere if possible) or solution stocks to reduce freeze–thaw and moisture exposure.
• Solution stability: aqueous solutions are best stored at 2–8°C for short term (hours–days) and at −20°C for longer term; avoid repeated freeze–thaw cycles. Protect from light when feasible.
• Drying: if anhydrous material is required, dry under high vacuum at ambient to mild temperature; verify water content by KF where critical (item-specific limits: Not specified for this item; refer to CoA/Spec Sheet).
• Compatibility: avoid strong acids/bases and oxidants during storage; maintain neutral pH in solution.

Disposal: dispose of unused material and solutions according to institutional and local regulations for organic laboratory chemicals.

For definitive stability, reconstitution solvent, and shelf-life specifications, consult the lot-specific CoA and SDS for SKU A1448011.

Structure and Identity

Item-specific identifiers (SMILES, InChIKey, CAS, molecular formula, molecular weight): Not specified for this item; refer to CoA/Spec Sheet.

General/literature description (for the common nucleoside adenosine):

• Adenosine is a ribonucleoside composed of the purine base adenine N9-glycosidically linked to β-D-ribofuranose.
• Structural features:
  • Heteroaromatic purine ring (6-5 fused ring) with an exocyclic amine at C6 (adenine) and ring nitrogens at positions 1, 3, 7, and 9.
  • β-D-ribofuranose (five-membered sugar) bearing three vicinal hydroxyls at 2′, 3′, and 5′.
  • One anomeric C–N glycosidic bond at N9 of adenine to the C1′ of ribose; natural stereochemistry at the ribose centers (2′R,3′R,4′S,5′R in conventional descriptors).
• 2D structure in words: a bicyclic purine ring with –NH2 substituent on the six-membered ring, attached through N9 to a five-membered sugar ring bearing primary CH2OH at 5′ and secondary OH at 2′ and 3′.

Important note: The product name “Adenosine:H20-C” suggests a specific variant or lot designation. Because defining identifiers are not provided here, treat all structural details above as general/literature information for adenosine; consult the product CoA to confirm exact identity and any isotopic/stabilizer content for this SKU.

Synthetic Utility

General/literature synthetic value of adenosine:

• Functional group manifold: exocyclic N6-amine (nucleophilic), three ribose hydroxyls (2′, 3′ secondary; 5′ primary), and a purine heteroaromatic core amenable to electrophilic/nucleophilic substitution at defined positions (e.g., C2, C8 after activation).
• Protecting group strategies:
  • Sugar OHs: silyl (TBDMS/TBS, TIPS) or acyl (Ac, Bz) protections; 5′-selective protection enables 2′/3′ differentiation (acyclic boronate, silylation, or cyclic acetal strategies).
  • Base: N6 protection (Bz, isobutyryl) to control reactivity and solubility in nucleoside synthesis.
• Key transformations:
  • 5′-Phosphorylation to AMP/ADP/ATP (chemical or enzymatic), and 5′-phosphoramidite formation for solid-phase RNA synthesis and 5′-labeling.
  • 2′-modifications (e.g., 2′-F, 2′-OMe, 2′-NH2) to modulate hybridization and nuclease resistance; often require temporary 3′,5′ protections and selective activation at 2′.
  • N6-derivatization to introduce probes, linkers, or affinity tags; reductive amination or acylation under mild conditions.
  • C8 functionalization via lithiation or electrophilic substitution on protected derivatives to access reporter-modified nucleosides.
• Analytical leverage: robust UV absorbance (≈260 nm, literature) allows reaction monitoring by HPLC/TLC.

Relevance to retrosynthesis: adenosine serves as a convergent node for assembling a wide array of adenosine analogs used in chemical biology, enzymology, and nucleic acid technology.

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

Target Specificity

Not applicable. This product is a small-molecule nucleoside, not an antibody or targeted biologic. No antigen/epitope, clone, isotype, or species reactivity information applies.

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