Geranyl pyrophosphate

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Geranyl pyrophosphate
Skeletal formula
Ball-and-stick model
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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Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of farnesyl pyrophosphate and geranylgeranyl pyrophosphate.[1] These species are respectively precursors to sesquiterpenes and diterpenes.[2]

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.

Related compounds

See also

References

  1. ^ "Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes". Topics in Current Chemistry. 209: 53–95. 2000. doi:10.1007/3-540-48146-X_2. ISBN 978-3-540-66573-1. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  2. ^ "Old Substrates for New Enzymes of Terpenoid Biosynthesis". Proceedings of the National Academy of Sciences of the United States of America. 106 (26): 10402–10403. 2009. Bibcode:2009PNAS..10610402B. doi:10.1073/pnas.0905226106. PMC 2705528. PMID 19553206. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

Further reading

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