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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Reaction: 2.5.1.39

Superclasses: Reactions Classified By Conversion Type Simple Reactions Chemical Reactions
Reactions Classified By Substrate Small-Molecule Reactions

EC Number: 2.5.1.39

Enzymes and Genes:
4-hydroxybenzoate-nonaprenyl transferase Inferred from experiment : plqA ( Synechocystis sp. PCC 6803 )
4-hydroxybenzoate polyprenyl diphosphate transferase Inferred from experiment : AT4G23660 ( Arabidopsis thaliana col )
4-hydroxybenzoate-polyprenyltransferase Inferred from experiment : ubiA ( Pseudomonas putida )
4-hydroxybenzoate polyprenyltransferase : PPT1 ( Arabidopsis thaliana )
4-hydroxybenzoate polyprenyltransferase : coq2 ( Schizosaccharomyces pombe 972h- )

In Pathway: ubiquinol-9 biosynthesis (eukaryotic) , ubiquinol-9 biosynthesis (prokaryotic) , plastoquinol-9 biosynthesis II

Note that this reaction equation differs from the official Enzyme Commission reaction equation for this EC number, which can be found here .

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

Mass balance status: Balanced.

Enzyme Commission Primary Name: 4-hydroxybenzoate polyprenyltransferase

Enzyme Commission Synonyms: nonaprenyl-4-hydroxybenzoate transferase, 4-hydroxybenzoate transferase, p-hydroxybenzoate dimethylallyltransferase, p-hydroxybenzoate polyprenyltransferase, p-hydroxybenzoic acid-polyprenyl transferase, p-hydroxybenzoic-polyprenyl transferase, 4-hydroxybenzoate nonaprenyltransferase

Standard Gibbs Free Energy (ΔrG in kcal/mol): -16.910004 Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary:
This enzyme, involved in the biosynthesis of ubiquinone, attaches a polyprenyl side chain to a 4-hydroxybenzoate ring, producing the first ubiquinone intermediate that is membrane bound. The number of isoprenoid subunits in the side chain varies in different species. The enzyme does not have any specificity concerning the length of the polyprenyl tail, and accepts tails of various lengths with similar efficiency [Melzer94, Forsgren04, Tran07a].

Citations: [Sadre11, Kalen90, Okada04a]

Gene-Reaction Schematic: ?

Instance reactions of [an isoprenoid diphosphate + 4-hydroxybenzoate = a 4-hydroxy-3-polyprenylbenzoate + diphosphate] (2.5.1.39):
i1: all-trans-heptaprenyl diphosphate + 4-hydroxybenzoate → 3-heptaprenyl-4-hydroxybenzoate + diphosphate (2.5.1.39)

i2: all-trans-hexaprenyl diphosphate + 4-hydroxybenzoate → 3-hexaprenyl-4-hydroxybenzoate + diphosphate (2.5.1.39)

i3: geranyl diphosphate + 4-hydroxybenzoate → 3-geranyl-4-hydroxybenzoate + diphosphate (2.5.1.93)

i4: all-trans-decaprenyl diphosphate + 4-hydroxybenzoate → 3-decaprenyl-4-hydroxybenzoate + diphosphate (2.5.1.39)

i5: all-trans-octaprenyl diphosphate + 4-hydroxybenzoate → 3-octaprenyl-4-hydroxybenzoate + diphosphate (2.5.1.39)

i6: all-trans-nonaprenyl diphosphate + 4-hydroxybenzoate → 3-nonaprenyl-4-hydroxybenzoate + diphosphate (2.5.1.39)

Unification Links: KEGG:R07273 , Rhea:17709

Relationship Links: BRENDA:EC:2.5.1.39 , ENZYME:EC:2.5.1.39 , IUBMB-ExplorEnz:EC:2.5.1.39

Credits:
Created 11-Jan-2012 by Caspi R , SRI International


References

Forsgren04: Forsgren M, Attersand A, Lake S, Grunler J, Swiezewska E, Dallner G, Climent I (2004). "Isolation and functional expression of human COQ2, a gene encoding a polyprenyl transferase involved in the synthesis of CoQ." Biochem J 382(Pt 2);519-26. PMID: 15153069

Kalen90: Kalen A, Appelkvist EL, Chojnacki T, Dallner G (1990). "Nonaprenyl-4-hydroxybenzoate transferase, an enzyme involved in ubiquinone biosynthesis, in the endoplasmic reticulum-Golgi system of rat liver." J Biol Chem 265(2);1158-64. PMID: 2295606

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

Melzer94: Melzer M, Heide L (1994). "Characterization of polyprenyldiphosphate: 4-hydroxybenzoate polyprenyltransferase from Escherichia coli." Biochim Biophys Acta 1994;1212(1);93-102. PMID: 8155731

Okada04a: Okada K, Ohara K, Yazaki K, Nozaki K, Uchida N, Kawamukai M, Nojiri H, Yamane H (2004). "The AtPPT1 gene encoding 4-hydroxybenzoate polyprenyl diphosphate transferase in ubiquinone biosynthesis is required for embryo development in Arabidopsis thaliana." Plant Mol Biol 55(4);567-77. PMID: 15604701

Sadre11: Sadre R, Pfaff C, Buchkremer S (2011). "Plastoquinone-9 biosynthesis in cyanobacteria differs from that in plants and involves a novel 4-hydroxybenzoate solanesyltransferase." Biochem J. PMID: 22166075

Tran07a: Tran UC, Clarke CF (2007). "Endogenous synthesis of coenzyme Q in eukaryotes." Mitochondrion 7 Suppl;S62-71. PMID: 17482885


Report Errors or Provide Feedback
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 18.5 on Wed Dec 17, 2014, biocyc13.