Geranyl pyrophosphate

Chemical compound From Wikipedia, the free encyclopedia

Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It is a precursor to many thousands of natural products.[1]

Quick facts Names, Identifiers ...
Geranyl pyrophosphate
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
(2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
MeSH Geranyl+pyrophosphate
  • InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+ checkY
    Key: GVVPGTZRZFNKDS-JXMROGBWSA-N checkY
  • InChI=1/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+
    Key: GVVPGTZRZFNKDS-JXMROGBWBE
  • O=P(O)(O)OP(=O)(OC/C=C(/CC\C=C(/C)C)C)O
Properties
C10H17O7P2
Molar mass 311.19
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Occurrence

GPP is an intermediate in the isoprenoid biosynthesis pathway that produces longer prenyl chains such as farnesyl pyrophosphate and geranylgeranyl pyrophosphate as well as many terpenes.[2] It can be prepared in the laboratory from geraniol.[3]

Isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) are condensed by geranyl pyrophosphate synthase (dimethylallyltranstransferase) to produce geranyl pyrophosphate (GPP) and pyrophosphate. The carbon skeletons of DMAPP and IPP have been colored to indicate their location in GPP.

Microbial toxicity

Intracellularly produced GPP has been shown to be toxic to the bacteria E. coli at moderate doses.[4]

Related compounds

See also

References

Further reading

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