|Superclasses:||Reactions Classified By Conversion Type → Simple Reactions → Chemical Reactions|
|Reactions Classified By Substrate → Small-Molecule Reactions|
EC Number: 18.104.22.168
Enzymes and Genes:
4-hydroxybenzoate-nonaprenyl transferase : plqA ( Synechocystis sp. PCC 6803 )
4-hydroxybenzoate polyprenyl diphosphate transferase : AT4G23660 ( Arabidopsis thaliana col )
4-hydroxybenzoate-polyprenyltransferase : ubiA ( Pseudomonas putida )
4-hydroxybenzoate polyprenyltransferase : PPT1 ( Arabidopsis thaliana )
4-hydroxybenzoate polyprenyltransferase : coq2 ( Schizosaccharomyces pombe 972h- )
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 [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].
Instance reactions of [an isoprenoid diphosphate + 4-hydroxybenzoate = a 4-hydroxy-3-polyprenylbenzoate + diphosphate] (22.214.171.124):
i1: geranyl diphosphate + 4-hydroxybenzoate → 3-geranyl-4-hydroxybenzoate + diphosphate (126.96.36.199)
i2: all-trans-heptaprenyl diphosphate + 4-hydroxybenzoate → 3-heptaprenyl-4-hydroxybenzoate + diphosphate (188.8.131.52)
i3: all-trans-hexaprenyl diphosphate + 4-hydroxybenzoate → 3-hexaprenyl-4-hydroxybenzoate + diphosphate (184.108.40.206)
i4: all-trans-decaprenyl diphosphate + 4-hydroxybenzoate → 3-decaprenyl-4-hydroxybenzoate + diphosphate (220.127.116.11)
i5: all-trans-octaprenyl diphosphate + 4-hydroxybenzoate → 3-octaprenyl-4-hydroxybenzoate + diphosphate (18.104.22.168)
i6: all-trans-nonaprenyl diphosphate + 4-hydroxybenzoate → 3-nonaprenyl-4-hydroxybenzoate + diphosphate (22.214.171.124)
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
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
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
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