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Isopentenyl pyrophosphate
Isopentenyl pyrophosphate
(IPP, isopentenyl diphosphate, or IDP)[1] is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway
HMG-CoA reductase pathway
(commonly called the mevalonate pathway) and in the non-mevalonate MEP pathway
MEP pathway
of isoprenoid precursor biosynthesis. Isoprenoid
Isoprenoid
precursors such as IPP, and its isomer DMAPP, are used by organisms in the biosynthesis of terpenes and terpenoids. Biosynthesis[edit] IPP is formed from acetyl-CoA via the mevalonate pathway (the "upstream" part), and then is isomerized to dimethylallyl pyrophosphate by the enzyme isopentenyl pyrophosphate isomerase.[2]

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. Please note the color scheme is for illustration only and does not correctly represent the origins of the isoprene units of GPP.

IPP can be synthesised via an alternative non-mevalonate pathway of isoprenoid precursor biosynthesis, the MEP pathway, where it is formed from (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP) by the enzyme HMB-PP reductase (LytB, IspH). The MEP pathway
MEP pathway
is present in many bacteria, apicomplexan protozoa such as malaria parasites, and in the plastids of higher plants.[3] See also[edit]

Dimethylallyltranstransferase

References[edit]

^ Banerjee, A.; Sharkey, T. D. (9 July 2014). "Methylerythritol 4-phosphate (MEP) pathway metabolic regulation". Natural Product Reports. 31 (8): 1043–1055. doi:10.1039/C3NP70124G.  ^ Chang, Wei-chen; Song, Heng; Liu, Hung-wen; Liu, Pinghua (2013). "Current development in isoprenoid precursor biosynthesis and regulation". Current Opinion in Chemical Biology. 17 (4): 571–579. doi:10.1016/j.cbpa.2013.06.020.  ^ Wiemer, AJ; Hsiao, CH; Wiemer, DF (2010). " Isoprenoid
Isoprenoid
metabolism as a therapeutic target in gram-negative pathogens". Current topics in medicinal chemistry. 10 (18): 1858–71. doi:10.2174/156802610793176602. PMID 20615187. 

v t e

Cholesterol
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

DOXP MEP CDP-ME CDP-MEP MEcPP HMB-PP IPP DMAPP

To Cholesterol

Farnesyl pyrophosphate Squalene 2,3-Oxidosqualene Lanosterol

Lanosterol Lathosterol 7-Dehydrocholesterol Cholesterol

Lanosterol Zymosterol 7-Dehydrodesmosterol Desmosterol Cholesterol

From Cholesterol (to steroids)

22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol

Steroid
Steroid
hormones

See here instead.

Nonhuman

Phytosterols

Stigmasterol Brassicasterol

Ergosterols

Ergosterol Ergocalciferol

v t e

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
Iridoid
glycosides (iridoids bound to a sugar) Steroids (4 rings)

Hemiterpenoids (1)

Isoprene
Isoprene
(C5H8) Prenol Isovaleric acid

Monoterpene
Monoterpene
(C10H16)(2)

Acyclic

Ocimene Myrcenes

Monocyclic

Limonene Terpinene Phellandrene Umbellulone

Bicyclic

Pinene
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
Sesquiterpenoids
(3)

Farnesyl pyrophosphate Artemisinin Bisabolol

Diterpenoids (4)

Geranylgeranyl pyrophosphate Gibberellin Retinol Retinal Phytol Taxol Forskolin Aphidicolin Salvinorin A

Sesterterpenoids (5)

geranylfarnesol

Triterpenoids (6)

Steroids

Phytosterols

Campesterol beta Sitosterol gamma sitosterol Stigmasterol

Tocopherols Cholesterol Testosterone Cholecalciferol
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
Terpene
synthase enzymes (many), having in common a Terpene
Terpene
synthase N terminal domain (protein domain)

Activated isoprene forms

Isopentenyl pyrophosphate
Isopentenyl pyrophosphate
(IPP) Dimethylallyl pyrophosphate
Dimethylallyl pyrophosphate
(DMAPP)

.