A phosphoantigen for Vγ9Vδ2 T cells
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HDMAPP (ammonium salt)

Item No. 13580

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
diphosphoric acid, mono[(2E)-4-hydroxy-3-methyl-2-butenyl] ester, triammonium salt
CAS Number
443892-56-6
Synonyms
  • HMBPP
Molecular Formula
C5H9O8P2 • 3NH4
Formula Weight
313.2
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
[O-]P(OP([O-])(OC/C=C(CO)\C)=O)([O-])=O.[NH4+].[NH4+].[NH4+]
InChi Code
InChI=1S/C5H12O8P2.3H3N/c1-5(4-6)2-3-12-15(10,11)13-14(7,8)9;;;/h2,6H,3-4H2,1H3,(H,10,11)(H2,7,8,9);3*1H3/b5-2+;;;
InChi Key
YPBALCNFFTVQJJ-JZWSQSCTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $84

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    1 mg

    $157

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    5 mg

    $653

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    10 mg

    $1,141

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    Product Description

    HDMAPP is a metabolite of the microbial dioxyxylulose-phosphate pathway, which is analogous to the isopentenyl pyrophosphate pathway in mammals. It is a protease-resistant and phosphatase-sensitive pyrophosphate produced by bacteria and plants.1,2 HDMAPP is a non-peptide ligand, also called a phosphoantigen, that binds the T cell receptor on Vγ9Vδ2 peripheral blood lymphocytes with high affinity (EC50 = 0.39 nM).3 It induces the expansion of human memory Vγ9Vδ2 T cells, but does not increase their ability to inhibit intracellular mycobacterial growth.4,5 Neonatal Vγ9Vδ2 T cells require micromolar concentrations of HDMAPP to drive expansion.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Poupot, M., and Fournié, J.J. Non-peptide antigens activating human Vγ9/Vδ2 T lymphocytes. Immunol. Lett. 95(2), 129-138 (2004).

    2. Tanaka, Y., Morita, C.T., Tanaka, Y., et al. Natural and synthetic non-peptide antigens recognized by human γδ T cells. Nature 375(6527), 155-158 (1995).

    3. 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(6), 1747-1754 (2008).

    4. DeBarros, A., Chevas-Ferreira, M., d'Orey, F., et al. CD70-CD27 interactions provide survival and proliferative signals that regulate T cell receptor-driven activation of human γδ peripheral blood lymphocytes. Eur. J. Immunol. 41(1), 195-201 (2011).

    5. Spencer, C.T., Abate, G., Blazevic, A., et al. Only a subset of phosphoantigen-responsive γ9δ2 T cells mediate protective TB immunity. J. Immunol. 181(7), 4471-4484 (2008).

    6. Moens, E., Brouwer, M., Dimova, T., et al. IL-23R and TCR signaling drives the generation of neonatal Vγ9Vδ2 T cells expressing high levels of cytotoxic mediators and producing IFN-γ and IL-17. J. Leukoc. Biol. 89(5), 743-752 (2011).