(E)-C-HDMAPP (ammonium salt)

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.^2,3 (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

(E)-C-HDMAPP (Ammonium Salt) is a useful research chemical compound used in the preparation of phosphoantigen salts of organic bases and methods for their crystallization.

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3. 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).
4. Bo?dec, 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).