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- Name help_outline isopentenyl diphosphate Identifier CHEBI:128769 Charge -3 Formula C5H9O7P2 InChIKeyhelp_outline NUHSROFQTUXZQQ-UHFFFAOYSA-K SMILEShelp_outline CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 38 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (2E,6E)-farnesyl diphosphate Identifier CHEBI:175763 Charge -3 Formula C15H25O7P2 InChIKeyhelp_outline VWFJDQUYCIWHTN-YFVJMOTDSA-K SMILEShelp_outline CC(C)=CCC\C(C)=C\CC\C(C)=C\COP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 183 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline all-trans-octaprenyl diphosphate Identifier CHEBI:57711 Charge -3 Formula C40H65O7P2 InChIKeyhelp_outline IKKLDISSULFFQO-DJMILUHSSA-K SMILEShelp_outline CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline diphosphate Identifier CHEBI:33019 (Beilstein: 185088) help_outline Charge -3 Formula HO7P2 InChIKeyhelp_outline XPPKVPWEQAFLFU-UHFFFAOYSA-K SMILEShelp_outline OP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,158 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:27798 | RHEA:27799 | RHEA:27800 | RHEA:27801 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Isoprenoid synthesis in Escherichia coli. Separation and partial purification of four enzymes involved in the synthesis.
Fujisaki S., Nishino T., Katsuki H.
Isopentenyl pyrophosphate (IPP) isomerase, farnesyl pyrophosphate (FPP) synthetase, octaprenyl pyrophosphate (OPP) synthetase and undecaprenyl pyrophosphate (UPP) synthetase were partially purified from Escherichia coli by DEAE-Toyopearl chromatography. FPP synthetase catalyzed the condensation of ... >> More
Isopentenyl pyrophosphate (IPP) isomerase, farnesyl pyrophosphate (FPP) synthetase, octaprenyl pyrophosphate (OPP) synthetase and undecaprenyl pyrophosphate (UPP) synthetase were partially purified from Escherichia coli by DEAE-Toyopearl chromatography. FPP synthetase catalyzed the condensation of IPP with dimethylallyl pyrophosphate (DPP) as well as with geranyl pyrophosphate (GPP) to yield FPP as final product. OPP synthetase and UPP synthetase catalyzed the condensation of IPP with FPP to yield OPP and cis,trans-polyprenyl pyrophosphates (the C45-, C50, and C55-compound), respectively. Neither DPP nor GPP acted as a priming substrate for either enzyme. These four enzymes required Mg2+ or Mn2+ for their activities. UPP synthetase required also Triton X-100 for its activity. The addition of Triton X-100 enhanced OPP synthetase, but it did not affect IPP isomerase and FPP synthetase. It seems possible that the combination of the four enzymes ensures the in vivo synthesis of long-chain isoprenoids in E. coli. << Less
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The identification of Escherichia coli ispB (cel) gene encoding the octaprenyl diphosphate synthase.
Asai K., Fujisaki S., Nishimura Y., Nishino T., Okada K., Nakagawa T., Kawamukai M., Matsuda H.
The gene located upstream of the nlp gene at min 69 on the chromosome of Escherichia coli was cloned from the plasmid pLC7-42 constructed by Clarke and Carbon. The extract of the strain harboring the plasmid containing this gene showed increased activity of the prenyltransferase. The product of th ... >> More
The gene located upstream of the nlp gene at min 69 on the chromosome of Escherichia coli was cloned from the plasmid pLC7-42 constructed by Clarke and Carbon. The extract of the strain harboring the plasmid containing this gene showed increased activity of the prenyltransferase. The product of the enzyme reaction was analyzed by two systems of the thin-layer chromatography and shown to be the phosphate ester of all-E-octaprenol. These results suggested that the gene was the structural gene for the octaprenyl diphosphate synthase which supplied the precursor of the side chain of the isoprenoid quinones. << Less
Biochem. Biophys. Res. Commun. 202:340-345(1994) [PubMed] [EuropePMC]