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Literature summary extracted from

  • Chen, A.P.; Chang, S.Y.; Lin, Y.C.; Sun, Y.S.; Chen, C.T.; Wang, A.H.; Liang, P.H.
    Substrate and product specificities of cis-type undecaprenyl pyrophosphate synthase (2005), Biochem. J., 386, 169-176.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.5.1.31 overexpression of His-tagged wild-type and mutant enzymes in strain BL21(DE3) Escherichia coli

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.5.1.31 co-crystal structure of UPPS in complex with (2E,6E)-farnesyl diphosphate Escherichia coli

Protein Variants

EC Number Protein Variants Comment Organism
2.5.1.31 F89A site-directed mutagenesis, mutant shows highly increased Km for isopentenyl diphosphate with farnesyl diphosphate and slightly with geranylgeranyl diphosphate compared to the wild-type enzyme Escherichia coli
2.5.1.31 F89A mutation increases (2E,6E)-farnesyl diphosphate and geranylgeranyl diphosphate Km values, indicating that these amino acids are important for substrate binding, but do not determine substrate specificity Escherichia coli
2.5.1.31 L85A site-directed mutagenesis, mutant shows highly increased Km for isopentenyl diphosphate with farnesyl diphosphate and slightly with geranylgeranyl diphosphate compared to the wild-type enzyme Escherichia coli
2.5.1.31 L85A mutation increases (2E,6E)-farnesyl diphosphate and geranylgeranyl diphosphate Km values, indicating that these amino acids are important for substrate binding, but do not determine substrate specificity Escherichia coli
2.5.1.31 L88A site-directed mutagenesis, mutant shows highly increased Km for isopentenyl diphosphate with farnesyl diphosphate and slightly with geranylgeranyl diphosphate compared to the wild-type enzyme Escherichia coli
2.5.1.31 L88A mutation increases (2E,6E)-farnesyl diphosphate and geranylgeranyl diphosphate Km values, indicating that these amino acids are important for substrate binding, but do not determine substrate specificity Escherichia coli

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.5.1.31 additional information farnesol (1 mM) lacking the diphosphate does not inhibit the UPPS reaction; no inhibition by farnesol Escherichia coli

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.5.1.31 additional information
-
 additional information steady-state kinetics, single turnover measurements with substrate geranylgeranyl diphosphate Escherichia coli
2.5.1.31 0.0003
-
 geranylgeranyl diphosphate pH 7.5, 25°C, wild-type enzyme Escherichia coli
2.5.1.31 0.0003
-
 geranylgeranyl diphosphate wild type, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.0004
-
 farnesyl diphosphate pH 7.5, 25°C, wild-type enzyme Escherichia coli
2.5.1.31 0.0004
-
 (2E,6E)-farnesyl diphosphate wild type, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.0007
-
 geranylgeranyl diphosphate pH 7.5, 25°C, mutant L88A Escherichia coli
2.5.1.31 0.0007
-
 geranylgeranyl diphosphate L88A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.001
-
 geranylgeranyl diphosphate pH 7.5, 25°C, mutant F89A Escherichia coli
2.5.1.31 0.001
-
 geranylgeranyl diphosphate F89A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.0012
-
 geranylgeranyl diphosphate pH 7.5, 25°C, mutant L85A Escherichia coli
2.5.1.31 0.0012
-
 geranylgeranyl diphosphate L85A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.0016
-
 farnesyl diphosphate pH 7.5, 25°C, mutant L85A Escherichia coli
2.5.1.31 0.0016
-
 (2E,6E)-farnesyl diphosphate L85A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.0021
-
 farnesyl diphosphate pH 7.5, 25°C, mutant L88A Escherichia coli
2.5.1.31 0.0021
-
 (2E,6E)-farnesyl diphosphate L88A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.0026
-
 farnesyl diphosphate pH 7.5, 25°C, mutant F89A Escherichia coli
2.5.1.31 0.0026
-
 (2E,6E)-farnesyl diphosphate F89A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.0041
-
 isopentenyl diphosphate pH 7.5, 25°C, wild-type enzyme, with farnesyl diphosphate Escherichia coli
2.5.1.31 0.0041
-
 isopentenyl diphosphate wild type, with (2E,6E)-farnesyl diphosphate, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.013
-
 isopentenyl diphosphate pH 7.5, 25°C, wild-type enzyme, with geranylgeranyl diphosphate Escherichia coli
2.5.1.31 0.013
-
 isopentenyl diphosphate wild type, with geranylgeranyl diphosphate, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.018
-
 isopentenyl diphosphate pH 7.5, 25°C, mutant F89A, with geranylgeranyl diphosphate Escherichia coli
2.5.1.31 0.018
-
 isopentenyl diphosphate F89A mutant, with geranylgeranyl diphosphate, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.036
-
 geranyl diphosphate 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.042
-
 isopentenyl diphosphate pH 7.5, 25°C, mutant L88A, with geranylgeranyl diphosphate Escherichia coli
2.5.1.31 0.042
-
 isopentenyl diphosphate L88A mutant, with geranylgeranyl diphosphate, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.06
-
 isopentenyl diphosphate pH 7.5, 25°C, mutant L85A, with geranylgeranyl diphosphate Escherichia coli
2.5.1.31 0.06
-
 isopentenyl diphosphate L85A mutant, with geranylgeranyl diphosphate, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.084
-
 isopentenyl diphosphate pH 7.5, 25°C, mutant F89A, with farnesyl diphosphate Escherichia coli
2.5.1.31 0.084
-
 isopentenyl diphosphate F89A mutant, with (2E,6E)-farnesyl diphosphate, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.173
-
 isopentenyl diphosphate pH 7.5, 25°C, mutant L88A, with farnesyl diphosphate Escherichia coli
2.5.1.31 0.173
-
 isopentenyl diphosphate L88A mutant, with (2E,6E)-farnesyl diphosphate, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.617
-
 isopentenyl diphosphate pH 7.5, 25°C, mutant L85A, with farnesyl diphosphate Escherichia coli
2.5.1.31 0.617
-
 isopentenyl diphosphate L85A mutant, with (2E,6E)-farnesyl diphosphate, 25°C, pH 7.5 Escherichia coli

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
2.5.1.31 Mg2+
-
 Escherichia coli

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.31 farnesyl diphosphate + isopentenyl diphosphate Escherichia coli consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis, the final product has C55-C60 chain length, molecular 3D-structural modeling of the reaction product diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.31 Escherichia coli
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.31 (2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
-
 Escherichia coli 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
 ?
2.5.1.31 farnesyl diphosphate + isopentenyl diphosphate consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis, the final product has C55-C60 chain length, molecular 3D-structural modeling of the reaction product Escherichia coli diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
 ?
2.5.1.31 farnesyl diphosphate + isopentenyl diphosphate the phosphate head group of farnesyl diphosphate is bound to the positively charged Arg residues and the hydrocarbon moiety interacts with hydrophobic amino acids including L85, L88, and F89, located on the alpha3-helix of the enzyme Escherichia coli diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
 ?
2.5.1.31 farnesyl phosphate + isopentenyl diphosphate low activity Escherichia coli phosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
 ?
2.5.1.31 geranyl diphosphate + isopentenyl diphosphate less effective than farnesyl diphosphate Escherichia coli diphosphate + ?
-
 ?
2.5.1.31 geranyl diphosphate + isopentenyl diphosphate C10 GPP displays a 90fold larger Km value compared with (2E,6E)-farnesyl diphosphate Escherichia coli ?
-
 ?
2.5.1.31 geranylgeranyl diphosphate + isopentenyl diphosphate as effective as farnesyl diphosphate Escherichia coli diphosphate + ?
-
 ?
2.5.1.31 geranylgeranyl diphosphate + isopentenyl diphosphate containing a larger C20 hydrocarbon tail, is an equally good substrate Escherichia coli ?
-
 ?
2.5.1.31 isopentenyl diphosphate + isopentenyl diphosphate
-
 Escherichia coli ?
-
 ?
2.5.1.31 additional information role of the hydrocarbon moiety of the allylic substrate in the reaction Escherichia coli ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.5.1.31 cis-type undecaprenyl pyrophosphate synthase
-
 Escherichia coli
2.5.1.31 More cis-type enzyme Escherichia coli
2.5.1.31 undecaprenyl pyrophosphate synthase
-
 Escherichia coli
2.5.1.31 UPPs
-
 Escherichia coli

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.5.1.31 25
-
 assay at Escherichia coli

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.5.1.31 0.095
-
 farnesyl diphosphate pH 7.5, 25°C, mutant L85A Escherichia coli
2.5.1.31 0.095
-
 (2E,6E)-farnesyl diphosphate L85A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.18
-
 geranylgeranyl diphosphate pH 7.5, 25°C, mutant L85A Escherichia coli
2.5.1.31 0.18
-
 geranylgeranyl diphosphate L85A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.23
-
 farnesyl diphosphate pH 7.5, 25°C, mutant L88A Escherichia coli
2.5.1.31 0.23
-
 (2E,6E)-farnesyl diphosphate L88A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.32
-
 geranylgeranyl diphosphate pH 7.5, 25°C, mutant L88A Escherichia coli
2.5.1.31 0.32
-
 geranylgeranyl diphosphate L88A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.61
-
 farnesyl diphosphate pH 7.5, 25°C, mutant F89A Escherichia coli
2.5.1.31 0.61
-
 (2E,6E)-farnesyl diphosphate F89A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 0.7
-
 geranylgeranyl diphosphate pH 7.5, 25°C, mutant F89A Escherichia coli
2.5.1.31 0.7
-
 geranylgeranyl diphosphate F89A mutant, 25°C, pH 7.5 Escherichia coli
2.5.1.31 1.7
-
 geranyl diphosphate 25°C, pH 7.5 Escherichia coli
2.5.1.31 2.1
-
 geranylgeranyl diphosphate pH 7.5, 25°C, wild-type enzyme Escherichia coli
2.5.1.31 2.1
-
 geranylgeranyl diphosphate wild type, 25°C, pH 7.5 Escherichia coli
2.5.1.31 2.5
-
 farnesyl diphosphate pH 7.5, 25°C, wild-type enzyme Escherichia coli
2.5.1.31 2.5
-
 (2E,6E)-farnesyl diphosphate wild type, 25°C, pH 7.5 Escherichia coli

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.5.1.31 7.5
-
 assay at Escherichia coli