Farnesyl pyrophosphate

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Farnesyl pyrophosphate
Farnesylpyrophosphat.svg
Farnesyl-pyrophosphate-3D-balls.png
Names
Preferred IUPAC name
(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate
Identifiers
  • 13058-04-3 Yes check.svgY
ChemSpider
MeSH farnesyl+pyrophosphate
PubChem CID
UNII
Properties
C15H28O7P2
Molar mass 382.326
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

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).

Contents

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:

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Cholesterol-Synthesis-Reaction9.png

Pharmacology

The above reactions are inhibited by bisphosphonates (used for osteoporosis). [3] Farnesyl pyrophosphate is a selective agonist of TRPV3. [4]

Related Research Articles

Terpene Class of oily organic compounds found in plants

Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes are further classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), etc. A well known monoterpene is alpha-pinene, a major component of turpentine.

Dimethylallyl pyrophosphate Chemical compound

Dimethylallyl pyrophosphate is an isoprenoid precursor. It is a product of both the mevalonate pathway and the MEP pathway of isoprenoid precursor biosynthesis. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. The enzyme isopentenyl pyrophosphate isomerase catalyzes isomerization between DMAPP and IPP.

Sabinene Chemical compound

Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated from the essential oils of a variety of plants including holm oak (Quercus ilex) and Norway spruce (Picea abies). It has a strained ring system with a cyclopentane ring fused to a cyclopropane ring.

Isopentenyl pyrophosphate Chemical compound

Isopentenyl pyrophosphate is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway and in the non-mevalonate MEP pathway of isoprenoid precursor biosynthesis. Isoprenoid precursors such as IPP, and its isomer DMAPP, are used by organisms in the biosynthesis of terpenes and terpenoids.

Geranyl pyrophosphate Chemical compound

Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is an intermediate in the isoprenoid biosynthesis pathway that produces longer prenyl chains such as farnesyl pyrophosphate and geranylgeranyl pyrophosphate as well as terpenes. GPP is a precursor to monoterpenes.

Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and diterpenoids. It is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls.

Sesquiterpene

Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids.

In enzymology, a (+)-delta-cadinene synthase is an enzyme that catalyzes the chemical reaction

Farnesyl-diphosphate farnesyltransferase

Squalene synthase (SQS) or farnesyl-diphosphate:farnesyl-diphosphate farnesyl transferase is an enzyme localized to the membrane of the endoplasmic reticulum. SQS participates in the isoprenoid biosynthetic pathway, catalyzing a two-step reaction in which two identical molecules of farnesyl pyrophosphate (FPP) are converted into squalene, with the consumption of NADPH. Catalysis by SQS is the first committed step in sterol synthesis, since the squalene produced is converted exclusively into various sterols, such as cholesterol, via a complex, multi-step pathway. SQS belongs to squalene/phytoene synthase family of proteins.

Isopentenyl-diphosphate delta isomerase

Isopentenyl pyrophosphate isomerase, also known as Isopentenyl-diphosphate delta isomerase, is an isomerase that catalyzes the conversion of the relatively un-reactive isopentenyl pyrophosphate (IPP) to the more-reactive electrophile dimethylallyl pyrophosphate (DMAPP). This isomerization is a key step in the biosynthesis of isoprenoids through the mevalonate pathway and the MEP pathway.

Bornyl diphosphate synthase

In enzymology, bornyl diphosphate synthase (BPPS) is an enzyme that catalyzes the chemical reaction

In enzymology, a farnesyltranstransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a geranyltranstransferase is an enzyme that catalyzes the chemical reaction

Juvabione Chemical compound

Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid, both of which are sesquiterpenes (C15) found in the wood of true firs of the genus Abies. They occur naturally as part of a mixture of sesquiterpenes based upon the bisabolane scaffold. Sesquiterpenes of this family are known as insect juvenile hormone analogues (IJHA) because of their ability to mimic juvenile activity in order to stifle insect reproduction and growth. These compounds play important roles in conifers as the second line of defense against insect induced trauma and fungal pathogens.

Hexaprenyl-diphosphate synthase is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase . This enzyme catalyses the following chemical reaction

All-trans-nonaprenyl-diphosphate synthase is an enzyme with systematic name geranyl-diphosphate:isopentenyl-diphosphate transtransferase . This enzyme catalyses the following chemical reaction

(2Z,6Z)-farnesyl diphosphate synthase is an enzyme with systematic name dimethylallyl-diphosphate:isopentenyl-diphosphate cistransferase . This enzyme catalyses the following chemical reaction

(+)-car-3-ene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

(+)-camphene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

(+)-alpha-pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

References

  1. 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.
  2. 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.
  3. 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.
  4. 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.