Geranyl pyrophosphate
{{chembox
| Verifiedfields = changed
| verifiedrevid = 461119902
| ImageFile = Geranylpyrophosphat.svg
| ImageSize = 220px
| ImageName = Skeletal formula
| ImageFile1 = Geranyl-pyrophosphate-3D-balls.png
| ImageSize1 = 240px
| ImageName1 = Ball-and-stick model
| PIN = (2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphate
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 3051
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 393471
| 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+
| InChIKey = GVVPGTZRZFNKDS-JXMROGBWBE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GVVPGTZRZFNKDS-JXMROGBWSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo=763-10-0
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 41342
| PubChem=445995
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02552
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17211
| SMILES = O=P(O)(O)OP(=O)(OC/C=C(/CC\C=C(/C)C)C)O
| MeSHName=Geranyl+pyrophosphate
}}
|Section2={{Chembox Properties
| Formula=C10H17O7P2
| MolarMass=311.19
}}
}}
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.{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }}
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.{{cite journal|title=Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes|author1=Davis, Edward M. |author2=Croteau, Rodney |journal=Topics in Current Chemistry|year=2000|volume=209|pages=53–95|doi=10.1007/3-540-48146-X_2|isbn=978-3-540-66573-1}} It can be prepared in the laboratory from geraniol.{{cite journal |doi=10.15227/orgsyn.066.0211|title=Trisammonium Geranyl Diphosphate |journal=Organic Syntheses |year=1988 |volume=66 |page=211|author=Andrew B. Woodside, Zheng Huang, C. Dale Poulter
}}
File:Synthesis of geranyl pyrophosphate.png (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.{{cite journal |last1=Sarria |first1=Stephen |last2=Wong |first2=Betty |last3=Martín |first3=Hector García |last4=Keasling |first4=Jay D. |last5=Peralta-Yahya |first5=Pamela |title=Microbial Synthesis of Pinene |url=https://pubs.acs.org/doi/10.1021/sb4001382 |journal=ACS Synthetic Biology |publisher=American Chemical Society |access-date=3 April 2023 |pages=466–475 |doi=10.1021/sb4001382 |date=18 July 2014|volume=3 |issue=7 |pmid=24679043 |doi-access=free }}
Related compounds
See also
References
{{reflist}}
==Further reading==
- Kulkarni RS, Pandit SS, Chidley HG, Nagel R, Schmidt A, Gershenzon J, Pujari KH, Giri AP and Gupta VS, 2013, [http://www.sciencedirect.com/science/article/pii/S0981942813002684 Characterization of three novel isoprenyl diphosphate synthases from the terpenoid rich mango fruit]. Plant Physiology and Biochemistry, 71, 121–131.
{{Cholesterol metabolism intermediates}}