Chemistry:Geranyl pyrophosphate
From HandWiki
| |
| |
| 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
|
|
| |
| |
| 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). | |
 verify (what is   ?)
| |
| Infobox references | |
Tracking categories (test):
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
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]
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.
Microbial toxicity
Intracellularly produced GPP has been shown to be toxic to the bacteria E. coli at moderate doses.[3]
Related compounds
See also
References
- ↑ 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.
- ↑ Sarria, Stephen; Wong, Betty; Martín, Hector García; Keasling, Jay D.; Peralta-Yahya, Pamela (18 July 2014). "Microbial Synthesis of Pinene". ACS Synthetic Biology (American Chemical Society) 3 (7): 466–475. doi:10.1021/sb4001382. https://pubs.acs.org/doi/10.1021/sb4001382. Retrieved 3 April 2023.
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.
 |  |
