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Merck

D4287

Sigma-Aldrich

γ,γ-Dimethylallyl pyrophosphate triammonium salt

1 mg/mL in methanol (:aqueous 10 mM NH4OH (7:3)), ≥90% (TLC)

Synonym(e):

DMAPP

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About This Item

Empirische Formel (Hill-System):
C5H12O7P2 · 3NH3
CAS-Nummer:
Molekulargewicht:
297.18
MDL-Nummer:
UNSPSC-Code:
12352106
PubChem Substanz-ID:
NACRES:
NA.25

Assay

≥90% (TLC)

Form

liquid

Verpackung

vial of 200 μg

Konzentration

1 mg/mL in methanol (:aqueous 10 mM NH4OH (7:3))

Lagertemp.

−20°C

SMILES String

N.N.N.C\C(C)=C\COP(O)(=O)OP(O)(O)=O

InChI

1S/C5H12O7P2.3H3N/c1-5(2)3-4-11-14(9,10)12-13(6,7)8;;;/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8);3*1H3

InChIKey

VBUNGGIXIOHBHL-UHFFFAOYSA-N

Verwandte Kategorien

Biochem./physiol. Wirkung

Intermediate in terpene biosynthesis

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2 - STOT SE 1

Zielorgane

Eyes,Central nervous system

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 2

Flammpunkt (°F)

69.8 °F - closed cup

Flammpunkt (°C)

21 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Lei Guo et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 69(5-6), 259-270 (2014-07-30)
Farnesyl pyrophosphate synthase (FPPS, EC 2.5.1.10) catalyzes the consecutive head-to-tail condensations of isopentenyl diphosphate (IPP) with dimethylallyl diphosphate (DMAPP) to form farnesyl pyrophosphate (FPP), a key precursor of sesquiterpenoids, triterpenoids, sterols, and farnesylated proteins. Here we report the molecular cloning
Keisuke Yoneyama et al.
Plant & cell physiology, 57(12), 2497-2509 (2016-12-18)
Soybean (Glycine max) accumulates several prenylated isoflavonoid phytoalexins, collectively referred to as glyceollins. Glyceollins (I, II, III, IV and V) possess modified pterocarpan skeletons with C
Carla Araya-Cloutier et al.
PloS one, 12(3), e0174665-e0174665 (2017-03-30)
Acceptor substrate specificity of Streptomyces roseochromogenes prenyltransferase SrCloQ was investigated using different non-genuine phenolic compounds. RP-UHPLC-UV-MSn was used for the tentative annotation and quantification of the prenylated products. Flavonoids, isoflavonoids and stilbenoids with different types of substitution were prenylated by
Khiem Nguyen et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 31(11), 4697-4706 (2017-07-15)
Small isoprenoid diphosphates, such as (
Xi Zhang et al.
Journal of chromatography. A, 1558, 115-119 (2018-05-19)
The natural rubber molecule is one of the end products of isoprenoids metabolism in the plant. Dimethylallyl diphosphate (DMAPP) and farnesyl pyrophosphate (FPP) are two typical isoprenoids which control the rate of biosynthesis and the molecular weight of natural rubber.

Artikel

Biosynthesis of cholesterol generally takes place in the endoplasmic reticulum of hepatic cells and begins with acetyl- CoA, which is mainly derived from an oxidation reaction in the mitochondria. Acetyl-CoA and acetoacetyl-CoA are converted to 3-hydroxy- 3-methylglutaryl-CoA (HMG-CoA) by HMG-CoA synthase.

Terpenes comprise the largest and most diverse class of secondary metabolites; approximately 55,000 compounds have been identified to date.

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