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Geranyl pyrophosphate





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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.

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

3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank

IUPHAR/BPS
MeSH Geranyl+pyrophosphate

PubChem CID

CompTox Dashboard (EPA)

  • 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).

☒N verify (what is checkY☒N ?)

Infobox references

Occurrence

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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

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Intracellularly produced GPP has been shown to be toxic to the bacteria E. coli at moderate doses.[3]

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See also

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References

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  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.
  • ^ 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

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    Last edited on 29 June 2024, at 19:47  





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    ●This page was last edited on 29 June 2024, at 19:47 (UTC).
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