(E)-C-HDMAPP (ammonium salt)

Synthetic and natural alkyl phosphates, also known as phosphoantigens, stimulate the proliferation of gammadelta-T lymphocytes. Isopentenyl pyrophosphate, and related derivatives including (E)-hydroxy-dimethyl-allyl pyrophosphate ((E)-HDMAPP), are particularly effective activators of gammadelta-T cells. (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. (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-alpha) by gammadelta-T lymphocytes with an IC50 value of 0.91 nM. (E)-C-HDMAPP also significantly increases the number of circulating gammadelta-T cells in vivo, in cynomolgus monkeys.Formal Name: P'-[(3E)-5-hydroxy-4-methyl-3-penten-1-yl]-isohypophosphoric acid, triammonium salt. CAS Number: 933030-60-5. Synonyms: (E)-5-hydroxy-4-methylpent-3-enyl pyrophosphate. Molecular Formula: C6H14O7P2 . 3NH4. Formula Weight: 311.2. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: PBS (pH 7.2): 10 mg/ml. SMILES: [O-]P(OP([O-])(CC/C=C(CO)\C)=O)([O-])=O.[NH4+].[NH4+].[NH4+]. InChi Code: InChI=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: VLHWKNAWRGFXCI-LESCHLGKSA-N.