Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Dimethylallyl pyrophosphate (DMAPP; or alternatively, dimethylallyl diphosphate (DMADP); also isoprenyl 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.[1]
In the mevalonate pathway DMAPP is synthesised from mevalonic acid. In contrast, DMAPP is synthesised from HMBPP in the MEP 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 pathwaySimplified 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.
^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 (17): 4294–4310. doi:10.1002/anie.201306712. PMC 3997630. PMID 24481599.
and 26 Related for: Dimethylallyl pyrophosphate information
Dimethylallylpyrophosphate (DMAPP; or alternatively, dimethylallyl diphosphate (DMADP); also isoprenyl pyrophosphate) is an isoprenoid precursor. It...
phosphorylated biological compound with inorganic phosphate, as for dimethylallylpyrophosphate. This bond is also referred to as a high-energy phosphate bond...
"upstream" part), and then is isomerized to dimethylallylpyrophosphate by the enzyme isopentenyl pyrophosphate isomerase. IPP can be synthesised via an...
isoprene units are provided in the form of dimethylallylpyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). DMAPP and IPP are structural isomers...
of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate, as is shown in the following two steps: Dimethylallylpyrophosphate reacts with 3-isopentenyl...
into dimethylallylpyrophosphate. This is then condensed with three molecules of isopentenyl pyrophosphate (an isomer of dimethylallylpyrophosphate), to...
ketone-containing carvone. In nature, limonene is formed from geranyl pyrophosphate, via cyclization of a neryl carbocation or its equivalent as shown....
chloroplasts of plants. One of the two end-products of MEP pathway, dimethylallylpyrophosphate (DMAPP), is cleaved by the enzyme isoprene synthase to form isoprene...
starts with three molecules of isopentenyl pyrophosphate (IPP) and one molecule of dimethylallylpyrophosphate (DMAPP) that are combined by IPP isomerase...
two five-carbon building blocks called isopentenyl pyrophosphate (IPP) and dimethylallylpyrophosphate (DMAPP), which are used to make isoprenoids, a diverse...
intermediates produced from geranyl pyrophosphate. Analogously hydrolysis of intermediates from farnesyl pyrophosphate gives sesquiterpenoids, and hydrolysis...
Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It...
biosynthesized through the head-to-head condensation of two farnesyl pyrophosphate units. This coupling converts a pair of C15 components into a C30 product...
units donated from the reactive precursors isopentenyl pyrophosphate and dimethylallylpyrophosphate. These precursors can be made in different ways. In...
isopentenyl pyrophosphate isomerase. Geranyl pyrophosphate is the precursor to monoterpenes (and hence monoterpenoids). Elimination of the pyrophosphate group...
atmosphere. The reaction of geranyl pyrophosphate with isopentenyl pyrophosphate results in the 15-carbon farnesyl pyrophosphate (FPP), which is an intermediate...
linalool are referred to as linalyl, e.g. linalyl pyrophosphate, an isomer of geranyl pyrophosphate. The word linalool is based on linaloe (a type of...
common a terpene synthase N terminal domain (protein domain) Activated isoprene forms Isopentenyl pyrophosphate (IPP) Dimethylallylpyrophosphate (DMAPP)...
common a terpene synthase N terminal domain (protein domain) Activated isoprene forms Isopentenyl pyrophosphate (IPP) Dimethylallylpyrophosphate (DMAPP)...
converts three monomers of isopentenyl pyrophosphate into farnesyl pyrophosphate. The farnesyl pyrophosphate can bind to rubber transferase to elongate...
elements, synthesized by living organisms from dimethylallylpyrophosphate (DMAPP) and/or isopentenyl pyrophosphate (IPP): Non-isoprenoid: Simple derivatives...
Archaea. Squalene is biosynthesised by coupling two molecules of farnesyl pyrophosphate. The condensation requires NADPH and the enzyme squalene synthase. Click...
building blocks of carotenoids are isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). These two isoprene isomers are used to create various...
the mevalonate pathway, which uses acetyl-CoA as building blocks for dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP).[better source needed]...
dimethylallylpyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP) into farnesylpyrophosphate (FPP). Pyrophosphate is also involved, as both a reactant and...
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