(E)-C-HDMAPP (ammonium salt) Exclusive

Cayman Chemical Item Number 13151

(​E)-5-hydroxy-4-methylpent-3-enyl pyrophosphate (CAS 933030-60-5)

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Description

Synthetic and natural alkyl phosphates, also known as phosphoantigens, stimulate the proliferation of γδ-T lymphocytes.1 Isopentenyl pyrophosphate, and related derivatives including (E)-hydroxy-dimethyl-allyl pyrophosphate ((E)-HDMAPP), are particularly effective activators of γδ-T cells.23 (E)-C-HDMAPP is the pyrophosphonate form of (E)-HDMAPP. The pyrophosphonate moiety in (E)-C-HDMAPP is much less susceptible to chemical or enzymatic hydrolysis than its pyrophosphate counterpart. As a result, (E)-C-HDMAPP is much more stable in solution and in vascular circulation.4 (E)-C-HDMAPP possesses comparable activity to (E)-HDMAPP, which is the most potent of the isoprenoid phosphoantigens. (E)-C-HDMAPP stimulates the synthesis of tumor necrosis factor (TNF-α) by γδ-T lymphocytes with an IC50 value of 0.91 nM.4 (E)-C-HDMAPP also significantly increases the number of circulating γδ-T cells in vivo, in cynomolgus monkeys.4

1. Tanaka, Y., Sano, S., Nieves, E., et al. Nonpeptide ligands for humanγδT cells. Proc Natl Acad Sci USA 91 8175-8179 (1994).

2. Poupot, M., and Fournié, J. Non-peptide antigens activating human Vg9/Vd2 T lymphocytes. Immunol Lett 95 129-138 (2004).

3. Tanaka, Y., Morita, C.T., Tanaka, Y., et al. Natural and synthetic non-peptide antigens recognized by humanγδT cells. Nature 375 155-158 (1995).

4. Boëdec, A., Sicard, H., Dessolin, J., et al. Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate. J Med Chem 51 1747-1754 (2008).

Synonyms
  • (​E)-5-hydroxy-4-methylpent-3-enyl pyrophosphate
Formal Name P’-​[(3E)-​5-​hydroxy-​4-​methyl-​3-​penten-​1-​yl]-​isohypophosphoric acid,​ triammonium salt
CAS Number 933030-60-5
Molecular Formula C6H14O7P2 • 3NH4
Formula Weight 311.2
Formulation A crystalline solid
Purity ≥95%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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[O-]​P(OP([O-]​)​(CC/C=C(CO)​\C)​=O)​([O-]​)​=O.[NH4+]​.[NH4+]​.[NH4+]​
InCHI Code
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​1S/C6H14O7P2.3H3N/c1-6(5-7)​3-2-4-14(8,9)​13-15(10,11)​12;;;/h3,7H,2,4-5H2,1H3,(H,8,9)​(H2,10,11,12)​;3*1H3/b6-3+;;;
InCHI Key
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VLHWKNAWRGFXCI-LESCHLGKSA-N

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Size Price Quantity Subtotal
500 µg $61.00 $0.00
1 mg $116.00 $0.00
5 mg $488.00 $0.00
10 mg $854.00 $0.00
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Pricing updated 2015-03-31. Prices are subject to change without notice.

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Related Products

DMAPP (ammonium salt)
HDMAPP (ammonium salt)

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