1. Product Overview
2-Fluorogeranyl Pyrophosphate (CAS 62163-14-8), also known as (Z)-2-fluoro-3,7-dimethylocta-2,6-dien-1-yl trihydrogen diphosphate, is a fluorinated analog of the natural isoprenoid diphosphate geranyl pyrophosphate (GPP). With the molecular formula C₁₀H₁₉FO₇P₂ and a molecular weight of 332.20 g/mol, this compound features a (2Z)-configured fluorinated geranyl backbone linked to a pyrophosphate (diphosphate) moiety. The strategic fluorine substitution at the 2-position blocks enzymatic deprotonation/isomerization, making it a valuable mechanistic probe for studying terpene synthases, prenyltransferases, and isoprenoid biosynthesis pathways in plants, bacteria, and eukaryotes.
2. Key Features and Benefits
• Mechanistic Probe for Terpene Synthases: The 2-fluoro substituent acts as a non-reactive mimic of the natural substrate's 2-methyl group while preventing ionization/cyclization, enabling researchers to trap reaction intermediates and elucidate terpene synthase catalytic mechanisms.
• Substrate/Inhibitor for Prenyltransferases: Serves as a substrate or competitive inhibitor (Kᵢ in the low μM range, literature-dependent) for prenyltransferases (e.g., farnesyl diphosphate synthase, geranylgeranyl diphosphate synthase), enabling kinetic and structural studies.
• Isoprenoid Biosynthesis Pathway Tool: Used to probe the mevalonate (MVA) and methylerythritol phosphate (MEP) pathways, dissecting the role of GPP/FPP/GGPP in protein prenylation, sterol biosynthesis, and plant secondary metabolism.
• Transition State Analog: The C–F bond at the 2-position mimics the developing carbocation in the rate-determining step of terpene cyclization, making it useful for co-crystallization with terpene synthases to visualize active site interactions.
• Z-Configuration: The (2Z) double bond geometry matches the natural GPP substrate configuration, ensuring biologically relevant enzyme interactions.
3. Major Applications
• Terpene Synthase Mechanistic Studies: Used to investigate the cyclization mechanisms of monoterpene synthases (e.g., limonene synthase, pinene synthase), sesquiterpene synthases, and diterpene synthases via trapping of reaction intermediates.
• Protein Prenylation Research: Employed in studies of protein farnesyltransferase (PFTase) and geranylgeranyltransferase (GGTase) activity, where fluorinated isoprenoids help elucidate prenylation specificity and processivity.
• Plant Biochemistry & Phytochemistry: Applied in assays of plant terpene synthase enzymes involved in the biosynthesis of essential oils, resin acids, and phytoalexins in conifers, grasses, and medicinal plants.
• Microbial Isoprenoid Metabolism: Used to study bacterial and fungal prenyltransferases and terpene cyclases, with applications in natural product drug discovery (e.g., antibiotic, antifungal, and anticancer terpenoids).
• Structural Biology: Co-crystallized with terpene synthases and prenyltransferases for X-ray crystallography or cryo-EM studies to map substrate binding pockets and catalytic residues.
• In Vivo Labeling Studies: Incorporated into intact plant or microbial systems to trace isoprenoid flux and identify novel terpene products via GC-MS and LC-MS analysis.
4. Technical Specifications
Item Description
Product Name 2-Fluorogeranyl Pyrophosphate (2-FGPP)
Synonyms 2-Fluorogeranyl Pyrophosphate; (Z)-2-Fluoro-3,7-dimethylocta-2,6-dien-1-yl trihydrogen diphosphate; [(2Z)-2-Fluoro-3,7-dimethylocta-2,6-dienyl] phosphono hydrogen phosphate; 0FV
CAS Number 62163-14-8
Molecular Formula C₁₀H₁₉FO₇P₂
Molecular Weight 332.20 g/mol
MDL Number —
PubChem CID 3037771
Assay (Purity) ≥95% (HPLC / Enzymatic assay)
Appearance Colorless to pale yellow liquid (room temperature)
Boiling Point ~494.6 °C @ 760 mmHg (Predicted)
Flash Point ~252.9 °C (Predicted)
Density ~1.388 g/cm³ (Predicted)
Refractive Index ~1.497 (Predicted)
pKa (Predicted) ~1.5 ± 0.5 (Diphosphate acidity); ~3.5 ± 0.5 (Secondary phosphates)
Calculated LogP ~3.2
Polar Surface Area (PSA) ~113.3 Ų
Hydrogen Bond Donors 3 (Diphosphate OH groups)
Hydrogen Bond Acceptors 8 (P=O, P–O⁻, F)
Rotatable Bonds 8
Solubility Soluble: Water (highly soluble as diphosphate salt), Dilute NaOH/KOH (pH adjustment), Methanol (slightly), DMSO (slightly).
Slightly Soluble:Ethanol, Acetone.
Insoluble:DCM, Chloroform, THF, Hexane, Ether.
Spectral Data (Predicted) ¹H NMR (D₂O, 400 MHz): δ 1.55 (s, 3H, =C-CH₃), 1.65 (s, 3H, =C-CH₃), 1.80–2.10 (m, 4H, CH₂-CH₂), 2.55 (t, J≈7.0 Hz, 2H, CH₂-CH=), 4.25 (d, J≈7.0 Hz, 2H, CH₂-OPP), 5.15 (t, J≈7.0 Hz, 1H, =CH-), 5.45 (br s, 1H, =CH-F).
¹³C NMR (D₂O):δ 18.0 (CH₃), 22.0 (CH₃), 25.5 (CH₂), 28.0 (CH₂), 38.0 (CH₂-OPP), 95.0 (d, J≈180 Hz, C-F), 120–145 (olefinic Cs), 165.0 (d, J≈20 Hz, C=C-F).
SMILES CC(C)=CCCC(C)=C(F)COP(=O)(O)OP(=O)(O)O
InChI Key BYJNSLXDWGDGAC-KTKRTIGZSA-N
Storage (Liquid/Solid) -20°C, sealed, under inert atmosphere (N₂/Ar), protected from light & moisture; stable ≥12–18 months
Sensitivity Hydrolyzes slowly in aqueous solution (pH-dependent); light-sensitive; store under N₂/Ar
HS Code 2915.90.90 / 2931.90.90
5. Storage and Handling
• Storage: Store in a tightly sealed container at -20°C (or -80°C for long-term), under an inert atmosphere (N₂ or Ar), protected from light and moisture. The diphosphate ester is susceptible to hydrolysis at elevated temperatures and acidic/basic pH. Stable for ≥12–18 months under proper conditions.
• Handling: Allow sealed container to warm to room temperature in an inert atmosphere (glovebox or Schlenk line) before opening to prevent condensation and hydrolysis. Handle quickly and reseal promptly. Minimize light exposure.
• Solution Preparation: Dissolve in cold water or dilute buffer (pH 6.5–7.5) immediately before use. The diphosphate is highly water-soluble. Avoid acidic or basic conditions that promote hydrolysis of the P–O–C bond.
• Enzymatic Assay Use: Add to enzyme assays on ice; include appropriate Mg²⁺ or Mn²⁺ cofactors as required by the target prenyltransferase or terpene synthase. Monitor reaction progress via HPLC, GC-MS, or radiometric methods.
• Solution Stability: Aqueous solutions are stable for several hours on ice; for longer storage, aliquot and freeze at -20°C. Avoid repeated freeze-thaw cycles.
6. Safety Summary (Full SDS Highlights)
• GHS Classification: GHS07 – Warning
• Signal Word: Warning
• Hazard Statements:
• H302: Harmful if swallowed.
• H315: Causes skin irritation.
• H319: Causes serious eye irritation.
• H335: May cause respiratory irritation.
• H373: May cause damage to organs (liver/kidney) through prolonged or repeated exposure (organophosphorus compound).
• Precautionary Statements:
• P261: Avoid breathing dust/mist/vapors. Use only in a well-ventilated area or fume hood.
• P264: Wash hands, forearms, and face thoroughly after handling.
• P270: Do not eat, drink, or smoke in areas where this material is used.
• P271: Use only outdoors or in a well-ventilated area.
• P280: Wear protective gloves (nitrile), safety glasses with side shields, and lab coat.
• P301+P312: IF SWALLOWED: Call a POISON CENTER or physician if you feel unwell.
• P302+P352: IF ON SKIN: Wash with plenty of soap and water.
• P304+P340: IF INHALED: Remove person to fresh air and keep comfortable for breathing.
• P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
• P330: Rinse mouth if swallowed.
• P337+P313: If eye irritation persists: Get medical advice/attention.
• P403+P233: Store in a well-ventilated place. Keep container tightly closed.
• P501: Dispose of contents/container in accordance with local, regional, and national regulations.
• First Aid Measures:
• Inhalation: Remove to fresh air. If breathing difficult, administer oxygen and seek medical attention.
• Skin Contact: Immediately wash with plenty of soap and water. Remove contaminated clothing. Seek medical advice if irritation or rash develops.
• Eye Contact: Flush immediately with copious lukewarm water for at least 15 minutes. Remove contact lenses if possible. Seek medical attention.
• Ingestion: Rinse mouth. Do NOT induce vomiting. Give water to drink if conscious. Seek medical advice.
• Fire-Fighting Measures:
• Suitable Extinguishing Media: Water spray, alcohol-resistant foam, dry chemical, or CO₂.
• Special Hazards: Combustion may produce highly toxic fumes including HF (hydrogen fluoride), P₂O₅ (phosphorus pentoxide), CO, and NOₓ. Hydrogen fluoride and phosphorus oxides are extremely toxic and corrosive.
• Protective Equipment: Wear self-contained breathing apparatus (SCBA) and full protective clothing.
• Spill Response:
• Absorb with inert material (sand, vermiculite). Do NOT use combustible materials for cleanup. Prevent runoff from entering waterways or drains. Ventilate area after cleanup.
• Handling & Storage:
• Handle in fume hood ONLY. Keep container closed when not in use. Store at -20°C, protected from light and moisture, under N₂/Ar. Keep away from strong oxidizers, strong acids/bases, and heat sources.
• Hazardous Decomposition Products: Hydrogen fluoride (HF), phosphorus oxides (P₂O₅, POₓ), nitrogen oxides (NOₓ), carbon monoxide (CO), carbon dioxide (CO₂).
• Intended Use: For laboratory research and development ONLY. Not for human or veterinary therapeutic, diagnostic, or food use. Handle as a potentially hazardous organophosphorus compound.
