Geranyl pyrophosphate

Geranyl pyrophosphate
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
  • 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+ Y
    Key: GVVPGTZRZFNKDS-JXMROGBWSA-N Y
  • 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
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 YN ?)
Infobox references

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]

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.[2] It can be prepared in the laboratory from geraniol.[3]

Microbial toxicity

Intracellularly produced GPP has been shown to be toxic to the bacteria E. coli at moderate doses.[4]

See also

References

  1. ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  2. ^ 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.
  3. ^ 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)
  4. ^ 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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