2-Fluoroadenosine - Moligand™, 10 mM in DMSO , CAS No.146-78-1

CAS: 146-78-1 Cat. No.: F1500400 Formula: C₁₀H₁₂FN₅O₄ Molecular Weight: 285.23 Beilstein Registry Number: 26(3/4)3723 EC Number: 633-923-8

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

2-Fluoroadenosine (2FA) is a nucleoside analogue. 2-Fluoroadenosine has antibacterial activity with IC 50 value of 0.842 mM for Vibrio microvibrio.

Specifications

Specifications & Purity

Moligand™, 10 mM in DMSO

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Names and Identifiers

Isomeric SMILES

C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)F)N

WGK Germany

3

RTECS

AU7386000

Molecular Weight

285.23

Beilstein

26(3/4)3723

Reaxy-Rn

3038524

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3038524&ln=

Chemical and Physical Properties

• Specific Rotation[α]: -72° (C=0.1,EtOH)
• Melt Point(°C): 200 °C

Application Protocols

No validated, item‑specific application protocols are provided for this catalog entry. The following general preparations are commonly used for nucleoside analogs in research settings (not product specifications):

• Stock solution preparation (biochemical assays)

  • Dissolve in molecular‑biology‑grade water to 10–100 mM, or in DMSO if higher concentration or long‑term frozen storage is required. Gentle warming (≤30 °C) and vortexing can assist dissolution. Filter (0.22 µm) if needed.

• Working solutions

  • Dilute into assay buffer to the desired concentration, keeping DMSO ≤1% v/v for sensitive systems. Prepare fresh daily when possible to minimize hydrolysis.

• Oligonucleotide synthesis precursor workup (if derivatized)

  • After protection/phosphitylation, purify intermediates by silica or RP‑HPLC under anhydrous or low‑moisture conditions. Confirm identity by 1H/13C NMR and LC‑MS.

Always adapt conditions to your system and consult peer‑reviewed literature for detailed, validated protocols.

Biological Roles

• Context (literature/general; for research use only)

  • 2‑Fluoroadenosine is a base‑modified adenosine analog. Fluorination at C2 perturbs hydrogen‑bonding patterns on the adenine ring and can reduce susceptibility to adenosine deaminase–mediated deamination, extending lifetime in enzymatic systems used for mechanistic studies.
  • Cellular metabolism: Like other nucleosides, it may be phosphorylated by cellular kinases to the corresponding nucleotide forms, enabling studies of polymerase selectivity and nucleotide processing enzymes. Extent and efficiency depend on the enzyme and cell type (literature variability).
  • Nucleic acid interactions: Incorporation into oligonucleotides (via the corresponding phosphoramidite) can modulate duplex stability and base‑pairing energetics, aiding structure–function investigations of RNA/DNA.

• Biophysical considerations

  • The electron‑withdrawing F at C2 affects the pKa of ring nitrogens and the H‑bond donor/acceptor balance at the Watson–Crick face of adenine, often impacting A–U/T pairing thermodynamics (literature observations).
  • UV absorbance remains in the 250–280 nm region typical of purines; slight bathochromic/hypsochromic shifts vs adenosine may occur depending on environment.

• Notes

  • No medical or therapeutic claims are made. Use solely for in vitro or ex vivo research, assay development, and biophysical/biochemical studies.

Buffer Applications

This compound is not a buffering agent and is not typically used to set or maintain pH. However, it is commonly dissolved in buffers for biochemical assays.

• Practical guidance (general)
  • Prepare stocks in water or DMSO; dilute into assay buffers such as HEPES, Tris, or phosphate at pH 7.0–8.0, avoiding strong acids/bases which can compromise the glycosidic bond.
  • Filter sterilization (0.22 µm) may be applied for cell‑free systems if sterility is required. Minimize DMSO content in biological assays (≤1% v/v typical).
  • For ion‑exchange or HPLC prep, use volatile buffers (e.g., ammonium bicarbonate/acetate) to facilitate lyophilization.

Green Alternatives

Although 2‑Fluoroadenosine itself is a solid reagent, greener choices primarily concern solvent and reagent selection during handling and derivatization.

• Greener solvent choices (general guidance)

  • Prefer water as primary medium for biochemical assays and ion‑exchange purifications.
  • Use ethanol over methanol when feasible (lower toxicity) for precipitation/solubilization.
  • Replace DMF/DCM with MeCN or 2‑MeTHF/ethyl acetate in protection steps where compatible; validate reaction selectivity.

• Greener reagents/conditions

  • Enzymatic phosphorylation (kinases) can substitute for P(V)/P(III) chemical methods, reducing hazardous phosphorus reagents and chlorinating agents.
  • Solid‑phase synthesis using greener activators and minimal solvent volumes (microflow or high‑efficiency columns) reduces waste.

• Comparison snapshot (general, literature)

  • Conventional: DCM, DMF, pyridine, chlorophosphoramidites → high EHS concerns.
  • Greener: MeCN/EtOAc/2‑MeTHF, aqueous biocatalysis, ethanol washes → lower toxicity/volatility; may require longer times or optimization.

• Trade‑offs

  • Greener solvents can alter solubility and selectivity; pilot reactions and in‑process analytics (HPLC) are essential to ensure comparable yields and impurity profiles.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item. It is supplied strictly for research use only.

• Research/manufacturing context (general)

  • May serve as a reference standard or analytical control for impurity profiling or method development in nucleoside‑related research programs.
  • Can be used to generate modified oligonucleotide intermediates for preclinical discovery chemistry, with all handling restricted to non‑clinical laboratories.

• Compliance note

  • Not manufactured to GMP and not intended for human or veterinary use. For regulated applications, obtain appropriate grade and documentation.

Physical Properties

Item-specific physico-chemical specifications have not been provided for this catalog entry. For lot-specific values, consult the CoA/Spec Sheet.

• Item-specific values

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting point: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility (spec): Not specified for this item; refer to CoA/Spec Sheet.
  • Water/peroxide/metal limits, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general properties (for context; not product specifications)

  • Physical state: Solid, polar nucleoside analog; typically highly soluble in water and polar aprotic solvents such as DMSO.
  • pKa (qualitative): Multiple basic/acidic sites on the purine and ribose; overall neutral at physiological pH; N6 amine is weakly basic; ring nitrogens weakly basic (literature, qualitative).
  • LogP: Expected very low/negative due to polyhydroxy ribose (literature, qualitative).
  • Hygroscopicity: Nucleosides can absorb moisture; handle quickly in ambient air and recap promptly (general guidance).

• Practical handling implications

  • Favor aqueous or DMSO stock solutions for assay use; filter sterilize if required for biological assays.
  • Avoid prolonged heating; nucleosides can undergo glycosidic cleavage and base modification under strong acid/base.

Quality & Grades

• Item-specific quality

  • Grade: Moligand™ (Aladdin small‑molecule/compound‑library grade). Intended for research screening, hit validation, and medicinal chemistry exploration. Not for clinical use.

• What Moligand™ signifies (general explanation)

  • Emphasis on identity and suitability for high‑throughput screening and SAR work. Typically supplied with analytical identity confirmation (e.g., HPLC/LC‑MS/NMR) appropriate for library compounds.
  • UV background and trace impurity limits are not inherently standardized under this library grade; consult the CoA for lot‑specific purity and analytical methods.

• Stabilizers/additives

  • None stated for this item. If stabilizers or salt forms are required for your application (e.g., hydrochloride salt for enhanced solubility), contact Technical Support.

• Documentation

  • For chromatography trace specs (e.g., residual solvents, inorganic ions, UV profile) and exact purity, defer to the item’s CoA/Spec Sheet. Where a particular analytical threshold is critical (e.g., oligo synthesis), verify against your internal acceptance criteria.

Reaction & Applications

• General application domains (literature/general)

  • Probe for adenosine‑processing enzymes: The 2‑fluoro substituent reduces susceptibility to adenosine deaminase (ADA) deamination, enabling kinetic and mechanistic studies of nucleoside metabolism.
  • Precursor to phosphorylated derivatives: Enzymatic or chemical synthesis of 5′‑mono/di/tri‑phosphates for biochemical assays (e.g., kinase, polymerase tolerance studies).
  • Oligonucleotide chemistry: After protection and conversion to the 3′‑cyanoethyl N,N‑diisopropyl phosphoramidite, it can be incorporated into RNA/DNA strands to modulate base‑pairing and stability (literature practice).

• Reaction families and considerations (general guidance)

  • Protection strategies: 5′‑OH typically protected as DMTr ether; 2′/3′‑OH protected (e.g., TBDMS, TOM, ACE) depending on RNA/DNA route. N6‑amine protected (e.g., benzoyl, isobutyryl) to control base reactivity.
  • Phosphorylation/phosphitylation: 5′‑OH activation with POCl3 or via phosphoramidite chemistry (2‑cyanoethyl diisopropylchlorophosphoramidite) under base (DIPEA) in dry ACN; water rigorously excluded.
  • Glycosidic stability: Avoid strong acid and prolonged heating; the N9‑glycosidic bond is acid‑labile. Maintain neutral to slightly basic conditions during workup.

• Practical tips

  • Use anhydrous solvents and molecular sieves for protection/phosphitylation steps.
  • Monitor reactions by RP‑HPLC with UV at 254–280 nm; the 2‑F substitution may slightly shift λmax relative to adenosine (literature observation).
  • For biochemistry, prepare fresh aqueous solutions and store aliquots at −80 °C to limit hydrolysis/degradation.

Reaction Conditions

The following are literature‑based, general guidelines for common manipulations of ribonucleosides and are not product specifications.

• Protection and phosphitylation (oligonucleotide building blocks)

  • 5′‑O‑DMTr protection: DMTrCl (1.2–1.5 eq) in dry pyridine or DCM with catalytic DMAP, 0–25 °C, 1–4 h; monitor by TLC/HPLC.
  • 2′/3′ protection (RNA): TBDMS‑Cl (2–3 eq) with imidazole in dry DMF, 25–50 °C; or TOM‑Cl under analogous conditions. Regioselectivity managed by solvent/base and temporary protecting groups.
  • Phosphitylation: 2‑cyanoethyl N,N‑diisopropylchlorophosphoramidite (1.5–2 eq), DIPEA (3–5 eq) in dry MeCN, 0–25 °C, 0.5–2 h; oxidation with mCPBA or t‑BuOOH.

• Aqueous phosphorylation (nucleotide synthesis)

  • POCl3 in trimethyl phosphate at 0–5 °C for 5′‑monophosphate formation; quench into buffered aqueous media and purify by ion‑exchange HPLC (literature protocols). Enzymatic kinase routes operate at pH 7–8, Mg2+ present, 25–37 °C.

• Stability notes

  • Avoid strong acid and prolonged heating; the N9‑glycosidic bond is acid‑labile. Maintain anhydrous conditions for P(III) chemistry; water <50 ppm is typically targeted in solvents (general practice).

• Analytical control

  • Use RP‑HPLC (C18) with water/MeCN + volatile buffer (e.g., ammonium acetate) for monitoring; detect at 254–280 nm. Mass spectrometry (ESI) readily confirms molecular ions due to polarity.

Safety & Handling

Safety data for this specific item have not been provided. Always review the SDS before use.

• GHS information (item-specific)

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements (H‑codes): Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General laboratory precautions (applicable to nucleoside analogs)

  • PPE: Laboratory coat, nitrile gloves, and safety glasses as minimum. Avoid inhalation of dust and contact with skin/eyes.
  • Engineering controls: Work in a fume hood or ventilated enclosure when weighing powders. Use closed containers for solutions.
  • Incompatibilities: Strong acids/bases (risk of glycosidic bond cleavage or amine protonation/deamination chemistry). Powerful oxidants may degrade the ribose moiety.
  • Thermal/light sensitivity: Protect from light as specified; avoid elevated temperatures.
  • First aid (overview): If inhaled—move to fresh air; skin/eye contact—rinse with water for several minutes; ingestion—rinse mouth. Seek medical attention as appropriate. Defer to SDS for authoritative instructions.

• Waste disposal

  • Collect aqueous/organic solutions of nucleosides as non-halogenated organic or aqueous lab waste per institutional and local regulations. Do not discharge to drain without approval.

Solvent Selection

2‑Fluoroadenosine is a highly polar, hydrogen‑bonding nucleoside. Choice of solvent influences stability (glycosidic bond), solubility, and downstream processing.

• Polarity/miscibility (general)

  • Aqueous buffers: Typically high solubility; compatible with neutral to mildly basic pH. Avoid strong acid/base.
  • Polar aprotic: DMSO and DMF dissolve nucleosides well; DMSO is generally preferred for biological stocks.
  • Alcohols: Methanol/ethanol can dissolve modestly to well; isopropanol less so.
  • Nonpolar solvents: Poor solubility in ethers, hexanes, chlorinated solvents without derivatization.

• Practical selection by use case

  • Screening assays: Prepare concentrated stocks (e.g., 10–100 mM) in DMSO; dilute into aqueous media ≤1% DMSO final to minimize vehicle effects (general guidance).
  • Enzymology: Use aqueous buffer (e.g., 10–50 mM HEPES/Tris, pH 7–8) with Mg2+/cofactors as required; pre-wet containers to minimize adsorption.
  • Synthetic transformations (protection/phosphorylation): Use dry DMF/DCM/ACN systems after appropriate protection; trace water strongly affects phosphitylation reactions.

• Comparison (general)

  • DMSO vs water: DMSO offers high solubility and freeze–thaw stability; water is preferred when DMSO is incompatible with the assay. Co-solvent systems (water/ACN) aid handling for lyophilization.

Storage & Reconstitution

• Item-specific storage/shipping

  • Storage conditions: Protected from light; Store at −80 °C (as provided in Product Data).
  • Shipped in: Dry ice packs + Cold packs (as provided in Product Data).

• Handling and aliquoting

  • Upon receipt, keep at −80 °C. Allow container to equilibrate to room temperature in a desiccator before opening to prevent condensation.
  • If frequent access is expected, prepare single‑use aliquots of solid (under dry atmosphere) or concentrated solution (e.g., in water or DMSO) and refreeze promptly.
  • Minimize freeze–thaw cycles; repeated cycling can promote hydrolysis/oxidation of nucleosides in solution.

• Reconstitution (general guidance)

  • Solvents: Water or DMSO are typical. Start with small volumes, vortex, and, if necessary, sonicate briefly. Adjust pH only with mild buffers; avoid strong acids/bases.
  • Sterile use: Pass through a 0.22 µm filter into sterile vials if sterility is required for cell‑free biochemical assays.

• Stability notes

  • Aqueous solutions are best stored as frozen aliquots at −80 °C, protected from light. For short‑term use, 2–8 °C for ≤24–48 h may be acceptable; verify by HPLC.

For exact shelf‑life and lot‑specific stability data, consult the CoA/Spec Sheet. For research use only.

Structure & Identity

Brief overview: 2‑Fluoroadenosine is a fluorinated ribonucleoside in which the adenine base bears a fluorine substituent at the C2 position. It retains the β-D-ribofuranose linked via an N9‑glycosidic bond to a 6‑aminopurine ring.

• Item-specific identifiers (from Product Data)

  • SKU: F1500400
  • Product name: 2‑Fluoroadenosine
  • CAS: 146-78-1
  • PubChem CID: 8975
  • Grade: Moligand™
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/reference identity (for context; not item-specific specifications)

  • Molecular formula (literature): C10H12FN5O4
  • Molecular weight (literature): ~285.24 g/mol
  • Common synonyms (literature): 2‑F‑Ado; 2‑Fluoro‑9‑β‑D‑ribofuranosyl‑6‑aminopurine

• Structural features (general description)

  • Heteroaromatic purine ring (adenine scaffold) bearing exocyclic N6‑amine and a ring fluorine at C2.
  • β‑D‑ribofuranose with three free hydroxyls (2′, 3′, 5′) in the unprotected nucleoside.
  • Key functional groups: primary alcohol (5′‑OH), vicinal diols (2′/3′‑OH), primary amine (N6), heteroaromatic N‑sites (N1, N3, N7, N9). Stereochemistry defined at ribose centers (D‑configuration).

Synthetic Utility

• Functional groups and reactivity (general)

  • Three alcohols (5′ primary; 2′/3′ secondary) enable selective protection, phosphorylation, and conjugation. The N6‑amine on adenine permits acylation/carbamate formation. The 2‑F substituent modulates base electronics and directs regioselectivity in electrophilic substitution on the purine.

• Key transformations (literature)

  • 5′‑O‑Phosphorylation to mono/di/tri‑phosphates (POCl3/trimethyl phosphate; or phosphoramidite followed by oxidation).
  • 5′‑O‑DMTr protection, 2′/3′‑O silyl protection (TBDMS, TOM) for RNA routes; subsequent conversion to 3′‑phosphoramidites for solid‑phase synthesis.
  • N6 protection (benzoyl/isobutyryl) to suppress base side reactions during phosphitylation.
  • Formation of conjugates at 5′‑OH (e.g., carbonate/carbamate/ester linkers) for probe development.

• Retrosynthetic value

  • Provides direct access to a base‑modified adenosine framework without requiring late‑stage electrophilic fluorination of purines or Vorbrüggen glycosylation, simplifying routes to 2‑F‑adenosine‑containing nucleotides/oligos.

Target Specificity

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