Geranyl pyrophosphate

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.

Geranyl pyrophosphate

Identifiers
CAS Number	763-10-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17211
ChEMBL	ChEMBL41342
ChemSpider	393471
DrugBank	DB02552
IUPHAR/BPS	3051
MeSH	Geranyl+pyrophosphate
PubChem CID	445995
InChI 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+ Key: GVVPGTZRZFNKDS-JXMROGBWSA-N 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
SMILES O=P(O)(O)OP(=O)(OC/C=C(/CC\C=C(/C)C)C)O
Properties
Chemical formula	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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Infobox references

Related compounds

• Geraniol
• Farnesyl pyrophosphate
• Geranylgeranyl pyrophosphate

See also

• Dimethylallyltranstransferase

References

1. Davis, Edward M.; Croteau, Rodney (2000). "Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes". Topics in Current Chemistry. 209: 53–95. doi:10.1007/3-540-48146-X_2. ISBN 978-3-540-66573-1.CS1 maint: uses authors parameter (link)
2. Bohlmann, Jorg; Gershenzon, Jonathan (2009). "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. Bibcode:2009PNAS..10610402B. doi:10.1073/pnas.0905226106. PMC 2705528. PMID 19553206.CS1 maint: uses authors parameter (link)

Further reading

• Kulkarni RS, Pandit SS, Chidley HG, Nagel R, Schmidt A, Gershenzon J, Pujari KH, Giri AP and Gupta VS, 2013, Characterization of three novel isoprenyl diphosphate synthases from the terpenoid rich mango fruit. Plant Physiology and Biochemistry, 71, 121–131.