(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate

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(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate
Chemical structure of HMB-PP
Ball-and-stick model, shown here as a 3- ion
IUPAC name
(E)-4-hydroxy-3-methylbut-2-enoxy-oxidophosphoryl phosphate
Other names
(E)-4-hydroxy-dimethylallyl pyrophosphate
HDMAPP
(E)-4-Hydroxy-3-methyl-but-2-enyl diphosphate
HMBDP
Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate (HMBPP or HMB-PP) is an intermediate of the non-mevalonate pathway of isoprenoid biosynthesis.[1][2] The enzyme HMB-PP synthase (GcpE, IspG) catalyzes the conversion of 2-C-methyl-D-erythritol 2,4-cyclopyrophosphate (MEcPP) into HMB-PP, and HMB-PP is then converted further to isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) by HMB-PP reductase (LytB, IspH).

HMB-PP is an essential metabolite in most pathogenic bacteria including Mycobacterium tuberculosis as well as in malaria parasites, but is absent from the human host.[3]

HMB-PP is the physiological activator ("phosphoantigen") for human Vγ9/Vδ2 T cells, the major γδ T cell population in peripheral blood. With a bioactivity of 0.1 nM it is 10,000-10,000,000 times more potent than any other natural compound, such as IPP or alkyl amines.[4]

References

  1. Rohmer, M; Rohmer, Michel (1999). "The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants". Natural product reports. 16 (5): 565–74. doi:10.1039/a709175c. PMID 10584331.
  2. Fox, DT; Poulter, CD (2002). "Synthesis of (E)-4-hydroxydimethylallyl diphosphate. An intermediate in the methyl erythritol phosphate branch of the isoprenoid pathway". The Journal of Organic Chemistry. 67 (14): 5009–10. doi:10.1021/jo0258453. PMID 12098326.
  3. Eisenreich, W; Bacher, A; Arigoni, D; Rohdich, F (2004). "Biosynthesis of isoprenoids via the non-mevalonate pathway". Cellular and molecular life sciences : CMLS. 61 (12): 1401–26. doi:10.1007/s00018-004-3381-z. PMID 15197467.
  4. Eberl, M; Hintz, M; Reichenberg, A; Kollas, AK; Wiesner, J; Jomaa, H (2003). "Microbial isoprenoid biosynthesis and human gammadelta T cell activation". FEBS Letters. 544 (1–3): 4–10. doi:10.1016/S0014-5793(03)00483-6. PMID 12782281.
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