(E)-C-HDMAPP (ammonium salt) • (E)-1-Hydroxy-2-Methylbut-2-enyl 4-Diphosphate (ammonium salt) (CAS 933030-60-5) || Cayman Chemical

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

Cayman Chemical Item Number 13151

(E)-1-Hydroxy-2-Methylbut-2-enyl 4-Diphosphate (ammonium salt) (CAS 933030-60-5)

(E)-C-HDMAPP (ammonium salt) (CAS 933030-60-5)

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)-1-Hydroxy-2-Methylbut-2-enyl 4-Diphosphate (ammonium salt)

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

Room temperature in continental US; may vary elsewhere

SMILES

Copy SMILES to clipboard

[O-]P(OP([O-])(CC/C=C(CO)\C)=O)([O-])=O.[NH4+].[NH4+].[NH4+]

Background Reading

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

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

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

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).

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500 µg 
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1 mg 
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10 mg 
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(E)-C-HDMAPP (ammonium salt) Exclusive

(E)-C-HDMAPP (ammonium salt) (CAS 933030-60-5)

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

(E)-C-HDMAPP (ammonium salt) (CAS 933030-60-5)

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