Geranyl pyrophosphate

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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

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]

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]

Microbial toxicity

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

Related compounds

References

^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
^ 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.
^ Andrew B. Woodside, Zheng Huang, C. Dale Poulter (1988). "Trisammonium Geranyl Diphosphate". Organic Syntheses. 66: 211. doi:10.15227/orgsyn.066.0211.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Sarria, Stephen; Wong, Betty; Martín, Hector García; Keasling, Jay D.; Peralta-Yahya, Pamela (18 July 2014). "Microbial Synthesis of Pinene". ACS Synthetic Biology. 3 (7). American Chemical Society: 466–475. doi:10.1021/sb4001382. PMID 24679043. Retrieved 3 April 2023.

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA
Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid
to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate
Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate
Carotenoid	Prephytoene diphosphate Phytoene

Non-mevalonate pathway

To Cholesterol

From Cholesterol
to Steroid hormones

Nonhuman

To Sitosterol	Cycloartenol Cycloeucalenol Obtusifoliol 4α-methylfecosterol Isofucosterol 24-Methylenelophenol Sitosterol More Phytosterols see here instead.
To Ergocalciferol	Fecosterol Episterol Ergostatrienol Ergostatetraenol Ergosterol Ergocalciferol

Categories:

Hidden categories:

Occurrence

Microbial toxicity

Related compounds

See also

References

Further reading