4.6.1.13: phosphatidylinositol diacylglycerol-lyase
This is an abbreviated version!
For detailed information about phosphatidylinositol diacylglycerol-lyase, go to the full flat file.
Word Map on EC 4.6.1.13
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4.6.1.13
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11beta-hydroxysteroid
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cortisone
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phosphatidylcholine-specific
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11beta-hsd2
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pc-plc
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molecular biology
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analysis
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medicine
- 4.6.1.13
- 11beta-hydroxysteroid
- cortisone
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phosphatidylcholine-specific
- 11beta-hsd2
- pc-plc
- molecular biology
- analysis
- medicine
Reaction
Synonyms
1-phosphatidyl-D-myo-inositol inositolphosphohydrolase (cyclic-phosphate-forming), 1-phosphatidylinositol phosphodiesterase, EC 3.1.4.10, monophosphatidylinositol phosphodiesterase, More, Phosphatidylinositol diacylglycerol-lyase, phosphatidylinositol phosphodiesterase, phosphatidylinositol phospholipase C, phosphatidylinositol-specific phospholipase C, phosphatidylinositol-specific PLC, phosphatidylinositolphospholipase C, PI-phospholipase C, PI-PLC, PLC, PLC1, PLC2, PLC3, PLC4, PLC5, PLC6
ECTree
4.6.1.13 phosphatidylinositol diacylglycerol-lyaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 4.6.1.13 - phosphatidylinositol diacylglycerol-lyase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + 1,2-diacyl-sn-glycerol
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + sn-1,2-diacylglycerol
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natural aggregate substrate, two-site enzyme model with interfacial cooperativity between the active site and a lipid-binding subsite, presumably adjacent to the active site
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?
butyl-fluorescein myo-inositol phosphate
D-myo-inositol 1,2-cyclic phosphate + butyl-fluorescein
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two substrate molecules bind to enzyme, one at the active site and one at a subsite, causing an increase in activity, subsite interactions of PI-PLC
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?
dibutyrylphosphatidylinositol
1D-myo-inositol 1,2-(cyclic)-phosphate + 1,2-dibutyryl-sn-glycerol
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is a poor substrate, necessitating long incubation times (2 to 5 h) if the same enzyme concentration is to be used in the absence and presence of salts and amphiphiles
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?
dihexanoylphosphorothioyl-myo-inositol
myo-inositol cis(2-OH,S)-1,6-cyclic phosphorothioate + 1,2-dihexanoyl-sn-glycerol
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?
methyl-fluorescein myo-inositol phosphate
D-myo-inositol 1,2-cyclic phosphate + methyl-fluorescein
phosphatidylinositol + H2O
diacylglycerol + myo-inositol 1,2-cyclic phosphate + D-myo-inositol 1-phosphate
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at first the enzyme catalyzes phosphate transfer within the molecule of phosphatidylinositol from glycerol OH to 2-OH of myo-inositol, resulting in diacylglycerol and myo-inositol 1,2-cyclic phosphate. Next myo-inositol 1,2-cyclic phosphate is hydrolyzed by the enzyme to inositol 1-phosphate. Since the reaction rate of the first step (phosphotransferase) is 1000 times as much as that of the second step (cyclic phosphodiesterase) myo-inositol 1,2-cyclic phosphate accumulates as one of the major products during enzyme action
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?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + 1,2-diacyl-sn-glycerol
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?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + 1,2-diacyl-sn-glycerol
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?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + 1,2-diacyl-sn-glycerol
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?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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natural substrate
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?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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a catalytic diad at the active site composed of Asp-274 and His-32 is involved in substrate-assisted catalysis, its function is to hydrogen-bond with the 2-OH of phosphatidylinositol to form a catalytic triad, catalytic mechanism
PI-PLC catalyzes in a second step the slow hydrolysis of 1D-myo-inositol 1,2-cyclic phosphate to form myo-inositol 1-phosphate
?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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cleaves phosphatidylinositol in a rapid intramolecular transphosphorylation reaction forming the products, in a second reaction the cyclic phosphorylase activity of PI-PLC catalyzes the slow hydrolysis of 1D-myo-inositol 1,2-cyclic phosphate to D-myo-inositol 1-phosphate, utilizes His-32 and His-82 in a general acid catalysis mechanism
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?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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catalytic mechanism, role of Arg-69, the bidentate nature of Arg-69 is the origin of the large thio effects and stereoselectivity in PI-PLC, its function is to bring the phosphate group and the 2-OH group of inositol into proximity and to induce proper alignment for nucleophilic attack, and possibly to lower the pKa of the 2-OH
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?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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PLC accepts only nonphosphorylated phosphatidylinositol substrates and produces cyclic inositol phosphate as final product, which is hydrolyzed at a 1000fold lower rate, catalytic mechanism, uses a guanidinium group of Arg-69 during catalysis
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?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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aggregated substrate is preferred over monomeric substrate
a cyclic phosphodiesterase activity of PI-PLC converts 1D-myo-inositol 1,2-cyclic phosphate to inositol 1-phosphate
?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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catalyzes the cleavage of the phosphorus-oxygen bond in phosphatidylinositol, catalytic role of aspartate in a short strong hydrogen bond of the Asp274-His32 catalytic dyad, catalytic mechanism, active site structure
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?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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general acid/general base mechanism, enhanced activity when phosphatidylinositol is present in an interface compared to monomeric substrate
PI-PLC catalyzes the hydrolysis of myo-inositol 1,2-cyclic phosphate to myo-inositol 1-phosphate
?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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the active site is located at the C-terminal side
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?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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Trp-47 and Trp-242 residues are important for enzyme to bind to interfaces, both activating zwitterionic and substrate anionic surfaces, micellar phosphatidylinositol is a better substrate than monomeric phosphatidylinositol
a cyclic phosphodiesterase activity of PI-PLC converts 1D-myo-inositol 1,2-cyclic phosphate to inositol 1-phosphate
?
1-phosphatidyl-1D-myo-inositol
1D-myo-inositol 1,2-cyclic phosphate + diacylglycerol
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natural aggregate substrate, PI-PLC is a virulence factor of the animal and human pathogen
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?
methyl-fluorescein myo-inositol phosphate
D-myo-inositol 1,2-cyclic phosphate + methyl-fluorescein
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substrate binds only to the active site and not to the activator site
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?
methyl-fluorescein myo-inositol phosphate
D-myo-inositol 1,2-cyclic phosphate + methyl-fluorescein
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monomeric substrate, only the D-enantiomer is active
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?
phosphatidylinositol
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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?
phosphatidylinositol
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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?
phosphatidylinositol
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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?
phosphatidylinositol + H2O
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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?
phosphatidylinositol + H2O
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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diacylglycerol and a mixture of myo-inositol 1-phosphate and myo-inositol 1,2-cyclic phosphate
?
phosphatidylinositol + H2O
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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?
phosphatidylinositol + H2O
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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myo-inositol-1,2-cyclic phosphate appears as sole product
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phosphatidylinositol + H2O
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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degrades synthetic phosphatidylinositols in the following order dilauroyl > dimyristoly > dioleoyl > dipalmitoyl. At first the enzyme catalyzes phosphate transfer within the molecule of phosphatidylinositol from glycerol OH to 2-OH of myo-inositol, resulting in diacylglycerol and myo-inositol 1,2-cyclic phosphate. Next myo-inositol 1,2-cyclic phosphate is hydrolyzed by the enzyme to inositol 1-phosphate. Since the reaction rate of the first step (phosphotransferase) is 1000 times as much as that of the second step (cyclic phosphodiesterase) myo-inositol 1,2-cyclic phosphate accumulates as one of the major products during enzyme action
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?
phosphatidylinositol + H2O
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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?
phosphatidylinositol + H2O
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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at first the enzyme catalyzes phosphate transfer within the molecule of phosphatidylinositol from glycerol OH to 2-OH of myo-inositol, resulting in diacylglycerol and myo-inositol 1,2-cyclic phosphate. Next myo-inositol 1,2-cyclic phosphate is hydrolyzed by the enzyme to inositol 1-phosphate. Since the reaction rate of the first step (phosphotransferase) is 1000 times as much as that of the second step (cyclic phosphodiesterase) myo-inositol 1,2-cyclic phosphate accumulates as one of the major products during enzyme action
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?
phosphatidylinositol + H2O
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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at first the enzyme catalyzes phosphate transfer within the molecule of phosphatidylinositol from glycerol OH to 2-OH of myo-inositol, resulting in diacylglycerol and myo-inositol 1,2-cyclic phosphate. Next myo-inositol 1,2-cyclic phosphate is hydrolyzed by the enzyme to inositol 1-phosphate. Since the reaction rate of the first step (phosphotransferase) is 1000 times as much as that of the second step (cyclic phosphodiesterase) myo-inositol 1,2-cyclic phosphate accumulates as one of the major products during enzyme action
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?
phosphatidylinositol + H2O
diacylglycerol + myo-inositol 1,2-cyclic phosphate
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specific for
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additional information
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Bacillus anthracis enzyme down-modulates dendritic cell function und T cell responses, possibly by cleaving GPI-anchored proteins important for TLR-mediated dendritic cell activation
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additional information
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the enzyme may have a role in Bacillus anthracis pathogenesis
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additional information
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enzyme from Bacillus anthracis unlike the ortholog from Listeria monocytogenes shows high activity on glycosylphosphatidylinositol-anchored proteins
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additional information
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approximately 20% of the alkaline phosphodiesterase I activity is released from the apical surface of the pig LLC-PK1 cells by the action of the 1-phosphatidylinositol phosphodiesterase
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additional information
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the enzyme exhibits cytotoxicity against some cultivated cells
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additional information
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Lys44 mediates the initial electrostatic interaction of the protein with substrate
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additional information
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Listeria monocytogenes phosphatidylinositol-specific phospholipase C is an important determinant of Listeria monocytogenes pathogenesis by absence of the Vb beta-strand, thus leading to greatly reduced activity on GPI-anchored proteins
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additional information
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the enzyme activates a host protein kinase C cascade which promotes escape of the bacterium from a macrophage-like cell phagosome
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additional information
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the enzyme contributes to listerial infection of epithelial cells and macrophages as a virulence factor cooperating with other factors such as listeriolysin O and phosphatidylcholine-preferring phospholipase C
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additional information
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ability to facilitate escape from the macrophage phagosome, is dependent on host PKCbeta
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additional information
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Phe237 is a key residue in the very tight binding of PI-PLC to membranes containing anionic phospholipids
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additional information
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ability to facilitate escape from the macrophage phagosome, is dependent on host PKCbeta
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additional information
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all PLCs are able to cleave GPI anchors
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additional information
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all PLCs are able to cleave GPI anchors
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additional information
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formation of inositol 1,2-(cyclic)phosphate from L-alpha-phoshatidylinositol, NMR spectroscopy analysis
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additional information
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synthesis of short-chain (dihexanoyl) analogues of phosphatidylinositol as substrates. The intermediate is generated from dihexanoylphosphorothioyl-myo-inositol identified as myo-inositol cis(2-OH,S)-1,6-cyclic phosphorothioate. The cyclic intermediate is gradually hydrolyzed to inositol 1-phosphorothioate. Both the Rp and Sp isomers of the phosphorodithioate analogue are readily cleaved, with the Sp isomer being hydrolyzed only ca. 6times more slowly than the Rp isomer. Rates of cleavage of two other substrates in which the pro-S oxygen is left unaltered, dihexanoylphosphorothioyl-myo-inositol and dihexanoylphosphatidyl inositol, are affected to only a small extent (0.6 and 1.6-fold, respectively) by the analogous modification of the bridging position. Strong Sp thio effect arises from a loss of a catalytic interaction rather than a steric effect
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additional information
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PI-PLC does not affect control transmembrane or membrane-associated proteins
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