Geranyl pyrophosphate

Geranyl pyrophosphate
Skeletal formula
Ball-and-stick model
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 checkY
ChEMBL
  • ChEMBL41342 checkY
ChemSpider
  • 393471 checkY
DrugBank
  • DB02552 checkY
IUPHAR/BPS
  • 3051
MeSH Geranyl+pyrophosphate
PubChem CID
  • 445995
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+ checkY
    Key: GVVPGTZRZFNKDS-JXMROGBWSA-N checkY
  • 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
  • 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).
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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

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

  1. ^ 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.
  2. ^ 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)
  3. ^ 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

  • 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.
  • v
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Mevalonate pathway
to HMG-CoA
Ketone bodies
to DMAPP
Geranyl-
Carotenoid
Non-mevalonate pathway
To CholesterolFrom Cholesterol
to Steroid hormones
  • 22R-Hydroxycholesterol
  • 20α,22R-Dihydroxycholesterol
  • See here instead.
Nonhuman
To Sitosterol
To Ergocalciferol
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