Metabolomics

Isoprene Biosynthesis

The 5-carbon isomers isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) are the fundamental building blocks used to synthesize key biological isoprenoids (terpenoids) including cholesterol and other steroids, carotenoids, saponins, and limonoids.

Two metabolic pathways exist for the biosynthesis of isopentenyl pyrophosphate and dimethylallyl pyrophosphate:

  • The mevalonate pathway, predominantly used by plants and in a few insect species
  • The non-mevalonate pathway or methyl D-erythritol 4-phosphate (MEP) pathway, which occurs in plant chloroplasts, algae, cyanobacteria, eubacteria, and important pathogens such as Mycobacterium tuberculosis and malaria parasites

Isoprene Biosynthesis

Mevalonate Pathway

The mevalonate pathway performs several key functions within cells and is an important central metabolic pathway in all higher eukaryotic cells. The key isomers dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP) are produced via the mevalonate pathway from (R)-mevalonate and its subsequent phosphorylated metabolites (R)-mevalonate-5-phosphate and (R)-mevalonate-pyrophosphate.

DMAPP and IPP are further utilized in condensation reactions for the biosynthesis of isoprenoids. These isoprenoids are transformed to more complex, cyclised structures through steroid and terpenoid biosynthesis and are involved in protein prenylation and protein anchoring. Mechanisms for feedback regulation of low-density lipoprotein receptors and enzymes involved in mevalonate biosynthesis ensure that sufficient mevalonate is available to generate the required quantity of DMAPP and IPP. The mevalonate pathway is of biomedical interest in certain types of cancer as well as heart disease, and a number of therapeutic drugs target this regulatory system.

Non-mevalonate (MEP) Pathway

The mevalonate-independent pathway for the biosynthesis of IPP and DMAPP was discovered in the 1990’s and consists of eight enzyme-catalyzed reactions. Synonyms for this pathway are the non-mevalonate pathway, the 1-deoxy-D-xylulose-5-phosphate pathway (DXP (or DOXP) pathway), and the 2C-methyl-D-erythritol-4-phosphate pathway, (MEP pathway).

The MEP pathway starts with the condensation of pyruvate and D-glyceraldehyde-3-phosphate to 1-deoxy-D-xylulose-5-phosphate (DXP or DOXP). The key isomers DMAPP and IPP are subsequently formed via a series of enzymatic steps starting with the conversion of DXP to 2C-methyl-D-erythritol-4-phosphate (MEP). Enzymes of this MEP pathway are attractive targets for the development of drugs targeting infectious diseases such as malaria and tuberculosis, because this pathway occurs in pathogenic prokaryotes but is absent in human metabolic pathways.

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Mevalonic Pathway Metabolites


Product No. Name   Biochemical/Physicological Actions
A2056 Acetyl coenzyme A sodium salt ≥93% (HPLC) Acetyl-CoA is an essential cofactor and carrier of acyl groups in enzymatic acetyl transfer reactions. It is formed either by the oxidative decarboxylation of pyruvate in mitochondria, by the oxidation of long-chain fatty acids, or by the oxidative degradation of certain amino acids. Acetyl-CoA is the starting compound for the citric acid cycle (Kreb's cycle). It is also a key precursor in lipid biosynthesis, and the source of all fatty acid carbons. Acetyl-CoA positively regulates the activity pyruvate carboxylase. It is a precursor of the neurotransmitter acetylcholine. Histone acetylases (HAT) use Acetyl-CoA as the donor for the acetyl group use in the post-translational acetylation reactions of histone and non-histone proteins.
A2181 Acetyl coenzyme A trilithium salt ~95% (HPLC) Acetyl-CoA is an essential cofactor and carrier of acyl groups in enzymatic acetyl transfer reactions. It is formed either by the oxidative decarboxylation of pyruvate in mitochondria, by the oxidation of long-chain fatty acids, or by the oxidative degradation of certain amino acids. Acetyl-CoA is the starting compound for the citric acid cycle (Kreb's cycle). It is also a key precursor in lipid biosynthesis, and the source of all fatty acid carbons. Acetyl-CoA positively regulates the activity pyruvate carboxylase. It is a precursor of the neurotransmitter acetylcholine. Histone acetylases (HAT) use Acetyl-CoA as the donor for the acetyl group use in the post-translational acetylation reactions of histone and non-histone proteins.
658650 Acetyl-1,2-13C2 coenzyme A lithium salt 99 atom % 13C, 95% (CP)  
54747 γ,γ-Dimethylallyl phosphate ammonium salt ≥93.0% (TLC)  
69579 γ,γ-Dimethylallyl pyrophosphate ammonium salt ≥93.0% (TLC) Intermediate in terpene biosynthesis
D4287 γ,γ-Dimethylallyl pyrophosphate triammonium salt 1 mg/mL in methanol (:aqueous 10 mM NH4OH (7:3)), ≥90% (TLC) Intermediate in terpene biosynthesis
H6132 DL-3-Hydroxy-3-methyl-glutaryl coenzyme A sodium salt ≥90% (HPLC) Key intermediate in the biosynthesis of terpenes, cholesterol, and ketone bodies.
18629 Isopentenyl phosphate dilithium salt ≥95.0% (TLC  
I0503 Isopentenyl pyrophosphate triammonium salt solution 1 mg/mL in methanol : aqueous 10 mM NH4OH (7:3), ≥95% (TLC) Intermediate in terpene biosynthesis.
00297 Isopentenyl pyrophosphate trilithium salt ≥95.0% (TLC) Intermediate in terpene biosynthesis.
41288 (R)-Mevalonic acid sodium salt ≥96.0% (qNMR)  
50838 (R)-Mevalonic acid lithium salt ≥93.0% (qNMR)  
79849 (±)-Mevalonic acid 5 phosphate trilithium salt hydrate 95% (TLC) Metabolite of the mevalonate pathway, which plays a key role in the biosynthesis of sterols, dolichol, heme and ubiquinone. Of interest for research in the disease areas oncology, autoimmune diseases, artherosclerosis and Alzheimer disease, as well as for inherited deficiencies of mevalonate kinase.
94259 (±)-Mevalonic acid 5 pyrophosphate tetralithium salt ≥80% (qNMR)  
77631 (R)-Mevalonic acid 5 pyrophosphate tetralithium salt ≥90% (qNMR)  
68519 (R)-(-)-Mevalonolactone ≥90.0% (GC) Classical enantiomerically pure metabolite in biosynthetic pathways leading to sterols, terpenes, carotenoids, and other natural products.
M4667 (±)-Mevalonolactone ~97% (titration)  
492469 Mevalonolactone-1-13C 99 atom % 13C, 98% (CP)  
486604 Mevalonolactone-2-13C 99 atom % 13C, 98% (CP)  
591270 Mevalonolactone-methyl-13C1 99 atom % 13C  
 
Non-Mevalonate Pathway Metabolites
Product No. Name   Biochemical/Physicological Actions
14764 1-Deoxy-D-xylulose ≥80% (TLC)  
13368 1-Deoxy-D-xylulose 5 phosphate sodium salt ≥99.0% (TLC) Metabolite of the non-mevalonate pathway, generally found in prokaryotes, as precursor to isoprenoids as well as non-isoprenoids like vitamins. As this pathway is not present in humans, it is of interest for the development of bacterium-specific drugs in the search for treatments of infectious diseases.
G5251 DL-Glyceraldehyde 3 phosphate solution 45-55 mg/mL in H2O  
18629 Isopentenyl phosphate dilithium salt ≥95.0% (TLC)  
I0503 Isopentenyl pyrophosphate triammonium salt solution 1 mg/mL in methanol : aqueous 10 mM NH4OH (7:3), ≥95% (TLC) Intermediate in terpene biosynthesis.
00297 Isopentenyl pyrophosphate trilithium salt ≥95.0% (TLC)  
41707 2-C-Methyl-D-erythritol ≥90% (GC)  
52131 2-C-Methyl-D-erythritol 4 phosphate lithium salt ≥98%  
107360 Pyruvic acid 98%  
P2256 Sodium pyruvate ReagentPlus® ≥99%  
490725 Sodium pyruvate-2-13C 99 atom % 13C  
490717 Sodium pyruvate-13C3 99 atom % 13C  

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