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MetaCyc Reaction: 2.5.1.39

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number: 2.5.1.39

Enzymes and Genes:

Arabidopsis thaliana: 4-hydroxybenzoate polyprenyltransferaseInferred from experiment: PPT1
Schizosaccharomyces pombe 972h-: 4-hydroxybenzoate polyprenyltransferaseInferred from experiment: coq2

The direction shown, i.e. which substrates are on the left and right sides, is in accordance with the Enzyme Commission system.

Mass balance status: Balance undetermined; a substrate lacks a chemical formula

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

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

all-trans-heptaprenyl diphosphate + 4-hydroxybenzoate → 3-heptaprenyl-4-hydroxybenzoate + diphosphate (2.5.1.39)

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

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

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

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

Taxonomic Range: Viridiplantae, Fungi, Metazoa

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, Tran07].

Citations: [Kalen90, Okada04]

Gene-Reaction Schematic

Gene-Reaction Schematic

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

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

i3: all-trans-heptaprenyl diphosphate + 4-hydroxybenzoate → 3-heptaprenyl-4-hydroxybenzoate + diphosphate (2.5.1.39)

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

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

i6: geranyl diphosphate + 4-hydroxybenzoate → 3-geranyl-4-hydroxybenzoate + diphosphate (2.5.1.93)

Unification Links: KEGG:R05000

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

Credits:
Created 07-Apr-2010 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

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

Okada04: 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

Tran07: 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 Pathway Tools version 19.5 (software by SRI International) on Wed Feb 10, 2016, biocyc14.