MetaCyc Pathway: heptaprenyl diphosphate biosynthesis

Enzyme View:

Pathway diagram: heptaprenyl diphosphate biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Biosynthesis Cofactors, Prosthetic Groups, Electron Carriers Biosynthesis Polyprenyl Biosynthesis

Some taxa known to possess this pathway include ? : Allochromatium vinosum , Bacillus alcalophilus , Bacillus amyloliquefaciens , Bacillus badius , Bacillus cereus , Bacillus circulans , Bacillus coagulans , Bacillus firmus , Bacillus licheniformis , Bacillus megaterium , Bacillus psychrosaccharolyticus , Bacillus pumilus , Bacillus racemilacticus , Bacillus subtilis , Bacillus thuringiensis , Brochothrix thermosphacta , Chlorobaculum thiosulfatiphilum , Desulfotomaculum nigrificans , Desulfuromonas acetoxidans , Exiguobacterium acetylicum , Flexibacter elegans , Geobacillus stearothermophilus , Listeria grayi , Pimelobacter simplex , Psychrobacillus insolitus , Sporolactobacillus inulinus , Sporosarcina ureae , Staphylococcus aureus , Staphylococcus capitis , Staphylococcus cohnii , Staphylococcus epidermidis , Staphylococcus haemolyticus , Staphylococcus hominis , Staphylococcus saprophyticus , Staphylococcus simulans , Staphylococcus warneri , Thermoplasma acidophilum , [Bacillus] aminovorans , [Brevibacterium] halotolerans

Expected Taxonomic Range: Archaea , Bacteria , Eukaryota

In this pathway multiple units of isopentenyl diphosphate (IPP) undergo a series of polymerizations to form a polyisoprenoid chain.

The sequential addition of isoprenyl units to (2E,6E)-farnesyl diphosphate is performed by polyprenyl diphosphate synthase enzymes such as the Escherichia coli enzyme octaprenyl diphosphate synthase.

Additional isoprenoid units are added to a maximal length that is determined by the specific enzyme. Most organisms generate polyprenyl chains of predominantly one length. Once completed, the polyprenyl chain is incorporated into other molecules, such as quinones. The enzyme that attaches the polyprenyl chain to the quinone precursor molecule does not have a preference towards a particular length. Thus, the length of the polyprenyl chain in the mature quinone molecule is determined by the predominant polyprenyl diphosphate synthase enzyme of the organism.

In most organisms there is one type of a predominant quinone, with a specific polyprenyl chain length. However, most organisms also have minor amounts of quinones with a different polyprenyl chain length.

Organisms whose main quinone contains a chain of 7 isoprenyl units include some Gram-negative bacteria (for example, the gliding bacterium Flexibacter elegans and the phototroph Allochromatium vinosum strain D), but mostly Gram-positive bacteria, such as many members of the Bacillus , Staphylococcus and Listeria genera. For a review detailing the polyprenyl chain length in different bacteria, see [Collins81].

Superpathways: superpathway of menaquinol-7 biosynthesis

Created 13-Feb-2008 by Caspi R , SRI International


Collins81: Collins MD, Jones D (1981). "Distribution of isoprenoid quinone structural types in bacteria and their taxonomic implication." Microbiol Rev 45(2);316-54. PMID: 7022156

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Sagami85: Sagami I, Fujii H, Koyama T, Ogura K (1985). "Heptaprenylpyrophosphate synthetase from Bacillus subtilis." Methods Enzymol 110;199-205. PMID: 3927112

Takahashi80: Takahashi I, Ogura K, Seto S (1980). "Heptaprenyl pyrophosphate synthetase from Bacillus subtilis." J Biol Chem 255(10);4539-43. PMID: 6768722

Yazdi90: Yazdi MA, Moir A (1990). "Characterization and cloning of the gerC locus of Bacillus subtilis 168." J Gen Microbiol 136(7);1335-42. PMID: 2121900

Zhang98a: Zhang YW, Koyama T, Marecak DM, Prestwich GD, Maki Y, Ogura K (1998). "Two subunits of heptaprenyl diphosphate synthase of Bacillus subtilis form a catalytically active complex." Biochemistry 37(38);13411-20. PMID: 9748348

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Wed Apr 1, 2015, biocyc14.