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Farnesyl pyrophosphate
Names
Preferred IUPAC name
(2E ,6E )-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate
Identifiers
ChemSpider
MeSH
farnesyl+pyrophosphate
UNII
InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
Key: VWFJDQUYCIWHTN-YFVJMOTDSA-N
CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)C
Properties
C 15 H 28 O 7 P 2
Molar mass
382.330 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Farnesyl pyrophosphate (FPP ), also known as farnesyl diphosphate (FDP ), is an intermediate in the biosynthesis of
terpenes and
terpenoids such as
sterols and
carotenoids .
[1] It is also used in the synthesis of
CoQ (part of the electron transport chain), as well as dehydrodolichol diphosphate (a precursor of
dolichol , which transports proteins to the
ER lumen for
N -glycosylation ).
Biosynthesis
Farnesyl pyrophosphate synthase (a
prenyl transferase )
[2] catalyzes sequential condensation reactions of
dimethylallyl pyrophosphate with 2 units of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate, as is shown in the following two steps:
Geranyl pyrophosphate then reacts with another molecule of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate
Pharmacology
The above reactions are inhibited by
bisphosphonates (used for
osteoporosis ).
[3] Farnesyl pyrophosphate is a
selective agonist of
TRPV3 .
[4]
Related compounds
References
^ Davis EM, Croteau R (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 .
S2CID
53419212 .
^ Kulkarni RS, Pandit SS, Chidley HG, Nagel R, Schmidt A, Gershenzon J, et al. (October 2013). "Characterization of three novel isoprenyl diphosphate synthases from the terpenoid rich mango fruit". Plant Physiology and Biochemistry . 71 : 121–131.
doi :
10.1016/j.plaphy.2013.07.006 .
PMID
23911730 .
^ Russell RG (April 2006). "Bisphosphonates: from bench to bedside". Annals of the New York Academy of Sciences . 1068 (April 2006): 367–401.
Bibcode :
2006NYASA1068..367R .
doi :
10.1196/annals.1346.041 .
PMID
16831938 .
S2CID
20706956 .
^ Bang S, Yoo S, Yang TJ, Cho H, Hwang SW (June 2010).
"Farnesyl pyrophosphate is a novel pain-producing molecule via specific activation of TRPV3" . The Journal of Biological Chemistry . 285 (25): 19362–71.
doi :
10.1074/jbc.M109.087742 .
PMC
2885216 .
PMID
20395302 .