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

From Wikipedia, the free encyclopedia

You have new messages (last change).
Chemical structure of HMB-PP
Chemical structure of HMB-PP

(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP) is an intermediate of the non-mevalonate pathway of isoprenoid biosynthesis. 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.

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 more potent than any other natural compound, such as IPP or alkyl amines.

[edit] References

  1. Rohmer M. The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants. Nat Prod Rep. 1999;16:565–74. PMID 10584331.
  2. Eberl M, Hintz M, Reichenberg A, Kollas AK, Wiesner J, Jomaa H. Microbial isoprenoid biosynthesis and human γδ T cell activation. FEBS Lett. 2003;544:4–10. PMID 12782281.
  3. Eisenreich W, Bacher A, Arigoni D, Rohdich F. Biosynthesis of isoprenoids via the non-mevalonate pathway. Cell Mol Life Sci. 2004;61:1401–26. PMID 15197467.
Retrieved from "http://en.wikipedia.org../../../%28/e/%29/%28E%29-4-Hydroxy-3-methyl-but-2-enyl_pyrophosphate_82a3.html"