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]
| |
| |
| 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 |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| 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).
| |
Occurrence
editGPP 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
editIntracellularly produced GPP has been shown to be toxic to the bacteria E. coli at moderate doses.[4]
Related compounds
editSee also
editReferences
edit- ^ 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.
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.