α-hydroxy Farnesyl Phosphonic Acid

Cayman Chemical Item Number 63420

Hydroxyfarnesyl Phosphate (CAS 148796-53-6)

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Description

α-hydroxy Farnesyl phosphonic acid is a nonhydrolyzable analog of farnesyl pyrophosphate which acts as a competitive inhibitor of farnesyl protein transferase (FPTase).1,2 At concentrations greater than 1 µM, α-hydroxy farnesyl phosphonic acid inhibits the processing of Ras in Ha-ras-transformed NIH3T3 cells.3

1. Pompliano, D.L., Rands, E., Schaber, M.D., et al. Steady-state kinetic mechanism of ras farnesyl: Protein transferase. Biochemistry 31 3800-3807 (1992).

2. Hohl, R.J., Lewis, K.A., Cermak, D.M., et al. Stereochemistry-dependent inhibition of Ras farnesylation by farnesylphosphonic acids. Lipids 33 39-46 (1998).

3. Gibbs, J.B., Pompliano, D.L., Mosser, S.D., et al. Selective inhibition of farnesyl-protein transferase blocks ras processing in vivo. J Biol Chem 268(11) 7617-7620 (1993).

Synonyms
  • Hydroxyfarnesyl Phosphate
Formal Name (±)-​1-​hydroxy-​3,​7,​11-​trimethyl-​2E,​6E,​10-​dodecatriene-​1-​phosphonic acid
CAS Number 148796-53-6
Molecular Formula C15H27O4P
Formula Weight 302.4
Formulation A crystalline solid
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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C/C(=C\CC\C(=C\C(O)​P(=O)​(O)​O)​\C)​/CCC=C(C)​C
InCHI Code
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​1S/C15H27O4P/c1-12(2)​7-5-8-13(3)​9-6-10-14(4)​11-15(16)​20(17,18)​19/h7,9,11,15-16H,5-6,8,10H2,1-4H3,(H2,17,18,19)​/b13-9+,14-11+
InCHI Key
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MONZTFSZTWQCKH-IJFRVEDASA-N

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α-hydroxy Farnesyl Phosphonic Acid is available in the following screening library:

Size Price Quantity Subtotal
1 mg $99.00 $0.00
5 mg $446.00 $0.00
10 mg $792.00 $0.00
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