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Information on EC 3.6.1.27 - undecaprenyl-diphosphate phosphatase
for references in articles please use BRENDA:EC3.6.1.27
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EC Tree 3 Hydrolases
3.6 Acting on acid anhydrides
3.6.1 In phosphorus-containing anhydrides
3.6.1.27 undecaprenyl-diphosphate phosphatase
IUBMB Comments
Isolated from the bacteria Micrococcus lysodeikticus , Escherichia coli [2,3,5,6] and Bacillus subtilis . The product of the reaction, ditrans,octacis-undecaprenyl phosphate, is essential for cell wall polysaccharide biosynthesis in these strains.
The enzyme appears in viruses and cellular organisms
- 3.6.1.27
- peptidoglycan
- phosphatases
- bacitracin
-
phosphatidic
- vancomycin
-
cell-wall
- phosphatidylglycerol
- flippase
- pyrophosphatases
- undecaprenol
- pharmacology
Reaction Schemes
showSynonyms
undecaprenyl pyrophosphate phosphatase, upp phosphatase, smu.244, c55-pp phosphatase, undecaprenyl diphosphate phosphatase, c55-pp pyrophosphatase, undecaprenyl pyrophosphatase, hp0851, undecaprenyl-diphosphate phosphatase, undecaprenyl-pyrophosphate phosphatase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
bacA
BcrC
C55-isoprenyl diphosphatase
-
-
-
-
C55-isoprenyl pyrophosphatase
-
-
-
-
C55-PP phosphatase
C55-PP pyrophosphatase
Dolicholpyrophosphatase
-
-
-
-
HP0851
HupA
isoprenyl pyrophosphatase
-
-
-
-
PbrB
SMU.244
Und-pp phosphatase
undecaprenyl pyrophosphatase
undecaprenyl pyrophosphate phosphatase
undecaprenyl-pyrophosphate phosphatase
UPP phosphatase
Upp-P
UppP
additional information
-
the enzyme is a member of the type 2 phosphatidic acid phosphatase family
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ditrans,octacis-undecaprenyl diphosphate + H2O = ditrans,octacis-undecaprenyl phosphate + phosphate
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
phosphorous acid anhydride hydrolysis
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
di-trans,poly-cis-undecaprenyl phosphate biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
ditrans,octacis-undecaprenyl-diphosphate phosphohydrolase
Isolated from the bacteria Micrococcus lysodeikticus [1], Escherichia coli [2,3,5,6] and Bacillus subtilis [4]. The product of the reaction, ditrans,octacis-undecaprenyl phosphate, is essential for cell wall polysaccharide biosynthesis in these strains.
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CAS REGISTRY NUMBER
COMMENTARY
9077-80-9
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
diphosphate + H2O
phosphate + phosphate
-
Substrates: low activity
Products: -
Products: -
?
ditrans,octacis-undecaprenyl diphosphate + H2O
ditrans,octacis-undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
4-nitrophenyl phosphate + H2O
4-nitrophenol + phosphate
-
Substrates: low activity
Products: -
Products: -
?
4-nitrophenyl phosphate + H2O
4-nitrophenol + phosphate
-
Substrates: low activity
Products: -
Products: -
?
diacylglycerol diphosphate + H2O
diacylglycerol phosphate + phosphate
-
Substrates: low activity
Products: -
Products: -
?
diacylglycerol diphosphate + H2O
diacylglycerol phosphate + phosphate
-
Substrates: low activity
Products: -
Products: -
?
diacylglycerol diphosphate + H2O
diacylglycerol phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
diacylglycerol diphosphate + H2O
diacylglycerol phosphate + phosphate
-
Substrates: relatively good substrate
Products: -
Products: -
?
diacylglycerol diphosphate + H2O
diacylglycerol phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
diacylglycerol diphosphate + H2O
diacylglycerol phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
farnesyl diphosphate + H2O
farnesyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
farnesyl diphosphate + H2O
farnesyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
farnesyl diphosphate + H2O
farnesyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
farnesyl diphosphate + H2O
farnesyl phosphate + phosphate
Substrates: -
Products: -
Products: -
?
farnesyl diphosphate + H2O
farnesyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
farnesyl diphosphate + H2O
farnesyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
farnesyl diphosphate + H2O
farnesyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
farnesyl diphosphate + H2O
farnesyl phosphate + phosphate
Streptococcus mutans WT UA159
-
Substrates: -
Products: -
Products: -
?
farnesyl diphosphate + H2O
farnesyl phosphate + phosphate
Substrates: -
Products: -
Products: -
?
isopentenyl diphosphate + H2O
isopentenyl phosphate + phosphate
-
Substrates: low activity
Products: -
Products: -
?
isopentenyl diphosphate + H2O
isopentenyl phosphate + phosphate
-
Substrates: low activity
Products: -
Products: -
?
isopentenyl diphosphate + H2O
isopentenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
isopentenyl diphosphate + H2O
isopentenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
phosphatidylglycerol phosphate + H2O
phosphatidylglycerol + phosphate
-
Substrates: -
Products: -
Products: -
?
phosphatidylglycerol phosphate + H2O
phosphatidylglycerol + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: involved in cyclic peptidoglycan pathway
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: low activity
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: the dephosphorylation of Und-PP, from de novo synthesis, produces undecaprenyl phosphate, a universal lipid carrier of glycan biosynthetic intermediates for carbohydrate polymers that are exported to the bacterial cell envelope, YbjG and YeiU are implicated in the recycling of periplasmic Und-PP molecules
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: the synthesis of the lipid carrier undecaprenyl phosphate, C55-P, requires the dephosphorylation of its precursor, undecaprenyl pyrophosphate, C55-PP, the dephosphorylation involves four integral membrane proteins, BacA, and three members of the type 2 phosphatidic acid phosphatase family, PgpB, YbjG, and YeiU, overview
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: involved in cyclic peptidoglycan pathway
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
Staphylococcus aureus USA 400
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
Streptococcus mutans WT UA159
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: undecaprenyl phosphate is no substrate, no activity on monophosphate compounds is observed. PbrB cannot dephosphorylate phosphatidic acid or glucose-6-phosphate
Products: -
Products: -
?
additional information
?
-
-
Substrates: undecaprenyl phosphate is no substrate, no activity on monophosphate compounds is observed. PbrB cannot dephosphorylate phosphatidic acid or glucose-6-phosphate
Products: -
Products: -
?
additional information
?
-
-
Substrates: substrate specificity, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: no activity with isopentenyl diphosphate, phosphatidylglycerol phosphate and phosphatidic acid
Products: -
Products: -
-
additional information
?
-
-
Substrates: no activity with phosphatidic acid
Products: -
Products: -
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additional information
?
-
-
Substrates: no activity with phosphatidic acid
Products: -
Products: -
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
ditrans,octacis-undecaprenyl diphosphate + H2O
ditrans,octacis-undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: involved in cyclic peptidoglycan pathway
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: the dephosphorylation of Und-PP, from de novo synthesis, produces undecaprenyl phosphate, a universal lipid carrier of glycan biosynthetic intermediates for carbohydrate polymers that are exported to the bacterial cell envelope, YbjG and YeiU are implicated in the recycling of periplasmic Und-PP molecules
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: the synthesis of the lipid carrier undecaprenyl phosphate, C55-P, requires the dephosphorylation of its precursor, undecaprenyl pyrophosphate, C55-PP, the dephosphorylation involves four integral membrane proteins, BacA, and three members of the type 2 phosphatidic acid phosphatase family, PgpB, YbjG, and YeiU, overview
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: involved in cyclic peptidoglycan pathway
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
Staphylococcus aureus USA 400
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
Streptococcus mutans WT UA159
-
Substrates: -
Products: -
Products: -
?
undecaprenyl diphosphate + H2O
undecaprenyl phosphate + phosphate
Substrates: -
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
Cd2+
-
enhances inhibitory effect of bacitacin, slight inhibitory effect without bacitracin
Co2+
Fe2+
-
enhances inhibitory effect of bacitacin, slight inhibitory effect without bacitracin
Mg2+
Mn2+
additional information
Ca2+
-
the enzyme activity lost after treatment with 0.05 mM EDTA is not only fully recovered following addition of Ca2+ (1 mM) but also greatly enhanced by an about 9fold factor
Ca2+
the enzyme has a requirement for divalent cations and is most active with calcium
Co2+
-
enhances inhibitory effect of bacitacin, slight inhibitory effect without bacitracin
Mg2+
-
the enzyme activity lost after treatment with 0.05 mM EDTA is fully recovered following addition of Mg2+ (1 mM)
Mn2+
-
enhances inhibitory effect of bacitacin, slight inhibitory effect without bacitracin
Mn2+
-
the enzyme activity lost after treatment with 0.05 mM EDTA is partially recovered following addition of Mn2+ (1 mM)
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-[3-(octyloxy)benzamido]-5-(trifluoromethoxy)benzoic acid
-
most potent inhibitor
tripropeptin C
tripropeptin C can potentially inhibit C55-PP phosphatase activity, which plays a crucial role in the lipid cycle of peptidoglycan synthesis
bacitracin
-
complex formation with substrate + metal ion, reversed by addition of chelating agents
additional information
-
the enzyme is not inhibited by Pb2+ (0.0001-10 mM)
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
diacylglycerol diphosphate
-
increases the activity with undecaprenyl diphosphate by about 400%
Lauryldimethylamine oxide
-
the enzyme shows optimal activity at 0.1% (v/v) lauryldimethylamine oxide (4.3 mM)
n-dodecyl beta-D-maltoside
the enzyme presents high activity, greater than 90%, with 0.02-1% (v/v) n-dodecyl beta-D-maltoside
n-dodecyl-beta-D-maltopyranoside
-
the enzyme activity appears optimal at low n-dodecyl-beta-D-maltopyranoside concentrations around 0.050-15% (v/v) (1-3 mM)
additional information
-
significant rise in activity at high ionic strength
-
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Bacterial Infections
Molecular insights into substrate binding mechanism of undecaprenyl pyrophosphate with membrane integrated phosphatidyl glycerophosphate phosphatase B (PgpB) using molecular dynamics simulation approach.
Tuberculosis
Mycobacterium tuberculosis gene Rv2136c is dispensable for acid resistance and virulence in mice.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00846
farnesyl diphosphate
mutant enzyme S167A, at pH 7.5 and 37°C
0.0106
farnesyl diphosphate
wild type enzyme, at pH 7.5 and 37°C
0.01127
farnesyl diphosphate
mutant enzyme S23A, at pH 7.5 and 37°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.52
farnesyl diphosphate
mutant enzyme S167A, at pH 7.5 and 37°C
1.67
farnesyl diphosphate
mutant enzyme S23A, at pH 7.5 and 37°C
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0065
2-(N-methyl-3-(octyloxy)benzamido)phenylphosphonic acid
Escherichia coli
-
at pH 7.5 and 20°C
0.2
2-methoxy-6-[3-(octyloxy)benzamido]benzoic acid
Escherichia coli
-
IC50 above 0.2 mM, at pH 7.5 and 20°C
0.2
2-[3,4-bis(2-methoxyethoxy)benzamido]-5-bromobenzoic acid
Escherichia coli
-
IC50 above 0.2 mM, at pH 7.5 and 20°C
0.2
2-[methyl[3-(octyloxy)benzoyl]amino]benzoic acid
Escherichia coli
-
IC50 above 0.2 mM, at pH 7.5 and 20°C
0.2
3,4,5-trimethoxy-2-[3-(octyloxy)benzamido]benzoic acid
Escherichia coli
-
IC50 above 0.2 mM, at pH 7.5 and 20°C
0.031
3-[3-(hexyloxy)benzamido]-4-hydroxybenzoic acid
Escherichia coli
-
pH and temperature not specified in the publication, mutant enzyme Y246D
0.2
3-[3-(octyloxy)benzamido]benzene-1,2-dicarboxylic acid
Escherichia coli
-
IC50 above 0.2 mM, at pH 7.5 and 20°C
0.031
4-hydroxy-3-[3-(octyloxy)benzamido]benzoic acid
Escherichia coli
-
at pH 7.5 and 20°C