Dimethylallyl pyrophosphate

Dimethylallyl pyrophosphate
Names


IUPAC name (hydroxy-(3-methylbut-2-enoxy) phosphoryl) oxyphosphonic acid
Other names Dimethylallyl diphosphate; isoprenyl pyrophosphate; isoprenyl diphosphate
Identifiers
CAS Number	358-72-5^Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	19951350^Y
MeSH	3,3-dimethylallyl+pyrophosphate
PubChem CID	647
InChI InChI=1S/C20H36O7P2/c1-13-17(5,6)23-28(21,24-18(7,8)14-2)27-29(22,25-19(9,10)15-3)26-20(11,12)16-4/h13-16H,1-4H2,5-12H3^Y Key: WTLAYXVNIWTZJI-UHFFFAOYSA-N^Y InChI=1/C20H36O7P2/c1-13-17(5,6)23-28(21,24-18(7,8)14-2)27-29(22,25-19(9,10)15-3)26-20(11,12)16-4/h13-16H,1-4H2,5-12H3 Key: WTLAYXVNIWTZJI-UHFFFAOYAD
SMILES CC(=CCOP(=O)(O)OP(=O)(O)O)C O=P(OP(=O)(OC(C)(C)C=C)OC(C)(C)C=C)(OC(C)(C)C=C)OC(C)(C)C=C
Properties
Chemical formula	C₅H₁₂O₇P₂
Molar mass	246.092
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Dimethylallyl pyrophosphate (DMAPP; or alternatively, -diphosphate (DMADP); also isoprenyl pyrophosphate) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. The enzyme isopentenyl pyrophosphate isomerase catalyzes the isomerization of DMAPP from IPP.^[1]

Precursor of DMAPP in the MVA pathway is mevalonic acid, and HMBPP in the MEP/DOXP pathway.

At present, it is believed that there is crossover between the two pathways in organisms that use both pathways to create terpenes and terpenoids, such as in plants, and that DMAPP is the crossover product.

Mevalonate pathway

Simplified version of the steroid synthesis pathway with the intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP) and squalene shown. Some intermediates are omitted.

References

↑ Wang, W.; Oldfield, E. (2014). "Bioorganometallic Chemistry with Ispg and Isph: Structure, Function, and Inhibition of the [Fe4s4] Proteins Involved in Isoprenoid Biosynthesis". Angew. Chem., Int. Ed. 53: 4294–4310. doi:10.1002/anie.201306712.

External links

Cholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA
Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid
to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate
Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate
Carotenoid	Prephytoene diphosphate Phytoene

Non-mevalonate pathway

To Cholesterol

From Cholesterol
(to steroids)

Steroid hormones

See here instead.

Nonhuman

Phytosterols	Stigmasterol Brassicasterol
Ergosterols	Ergosterol Ergocalciferol

Types of Terpenes and Terpenoids (# of isoprene units)

Basic forms:

Acyclic (linear, cis and trans forms)
Monocyclic (single ring)
Bicyclic (2 rings)
Iridoids (cyclopentane ring)
Iridoid glycosides (iridoids bound to a sugar)
Steroids (4 rings)

Hemiterpenoids (1)

Monoterpene (C₁₀H₁₆)(2)

Acyclic	Ocimene Myrcenes
Monocyclic	Limonene Terpinene Phellandrene Umbellulone
Bicyclic	Pinene (β and α Camphene Thujene Sabinene Carene

Monoterpenoids (2,modified)

Acyclic	Linalool Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate
Monocyclic	Grapefruit mercaptan menthol p-Cymene thymol Perillyl alcohol Carvacrol
Bicyclic	Camphor Borneol Eucalyptol Halomon Eucalyptol Pinene Ascaridole

Sesquiterpenoids (3)

Diterpenoids (4)

Sesterterpenoids (5)

geranylfarnesol

Triterpenoids (6)

Steroids	Phytosterols Campesterol beta Sitosterol gamma sitosterol Stigmasterol Tocopherols Cholesterol Testosterone Cholecalciferol (Vit D) Ecdysones
Other	Saponins Squalane Lanosterol Acids Oleanolic acid Ursolic acid Betulinic acid Moronic acid

Sesquarterpenes/oids (7)

ferrugicadiol
tetraprenylcurcumene

Tetraterpenoids
(Carotenoids) (8)

Carotenes	Alpha-Carotene Beta-Carotene Gamma-Carotene Delta-Carotene Lycopene Neurosporene Phytofluene Phytoene
Xanthophylls:	Canthaxanthin Cryptoxanthin Zeaxanthin Astaxanthin Lutein Rubixanthin

Polyterpenoids (many)

sap, resins, latex of many plants, e.g. rubber

Norisoprenoids (modified)

3-oxo-α-ionol
7,8-dihydroionone

Synthesis

Terpene synthase enzymes (many), having in common a Terpene synthase N terminal domain (protein domain)

Activated isoprene forms

Isopentenyl pyrophosphate (IPP)
Dimethylallyl pyrophosphate (DMAPP)

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