Contents

Geranyl pyrophosphate

Geranyl pyrophosphate

Names
Preferred IUPAC name (2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphate
Identifiers
CAS Number	763-10-0 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17211 Y
ChEMBL	ChEMBL41342 Y
ChemSpider	393471 Y
DrugBank	DB02552 Y
IUPHAR/BPS	3051
MeSH	Geranyl+pyrophosphate
PubChem CID	445995
CompTox Dashboard (EPA)	DTXSID801315430
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+ Y Key: GVVPGTZRZFNKDS-JXMROGBWSA-N Y 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). N verify (what is YN ?) Infobox references

Chemical compound

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 natural products.

Occurrence[edit]

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.^[1] It can be prepared in the laboratory from geraniol.^[2]

Microbial toxicity[edit]

Intracellularly produced GPP has been shown to be toxic to the bacteria E. coli at moderate doses.^[3]

Related compounds[edit]

• Geraniol
• Farnesyl pyrophosphate
• Geranylgeranyl pyrophosphate

See also[edit]

• Dimethylallyltranstransferase

References[edit]

Further reading[edit]

• 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.