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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 polyprenyltransferase Inferred from experiment : coq2 ( Schizosaccharomyces pombe 972h- )
4-hydroxybenzoate polyprenyltransferase Inferred from experiment : PPT1 ( Arabidopsis thaliana )

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: Undetermined; a substrate lacks a chemical formula

Instance reactions:
all-trans-heptaprenyl diphosphate + 4-hydroxybenzoate → 3-heptaprenyl-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)

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

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

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

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

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: [Kalen90, Okada04]

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: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

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 Mon Dec 22, 2014, biocyc12.