Information on EC 3.1.4.4 - phospholipase D

New: Word Map on EC 3.1.4.4
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Search Reference ID:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
3.1.4.4
-
RECOMMENDED NAME
GeneOntology No.
phospholipase D
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a phosphatidylcholine + H2O = choline + a phosphatidate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of phosphoric ester
-
-
-
-
transphosphatidylation
-
-
ethanol, aliphatic alcohols with more than 5 carbons e.g. geraniol, aromatic or heterocylic compounds, saccharides, polyalcohols, steroids serve as acceptors; methanol, ethanolamine, glycerol serve as acceptors; simultaneously to hydrolysis
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
choline biosynthesis III
-
-
Ether lipid metabolism
-
-
Glycerophospholipid metabolism
-
-
glycine betaine biosynthesis
-
-
Metabolic pathways
-
-
phosphatidate metabolism, as a signaling molecule
-
-
phospholipases
-
-
SYSTEMATIC NAME
IUBMB Comments
phosphatidylcholine phosphatidohydrolase
Also acts on other phosphatidyl esters.
CAS REGISTRY NUMBER
COMMENTARY hide
9001-87-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain ATCC 19606
-
-
Manually annotated by BRENDA team
diverse strains from soil, isolated from 25 soil samples in Setagaya, Tokyo, Japan
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
gene pld-1
-
-
Manually annotated by BRENDA team
madagascar periwinkles
-
-
Manually annotated by BRENDA team
patients with acute coronary syndromes infected with Chlamydophila pneumoniae
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
gene pldB
-
-
Manually annotated by BRENDA team
Duch
-
-
Manually annotated by BRENDA team
Duch
-
-
Manually annotated by BRENDA team
soybean
-
-
Manually annotated by BRENDA team
isozyme PLDalpha, gene PLD
UniProt
Manually annotated by BRENDA team
1218R
-
-
Manually annotated by BRENDA team
1218R
-
-
Manually annotated by BRENDA team
mc(2)155
-
-
Manually annotated by BRENDA team
mc(2)155
-
-
Manually annotated by BRENDA team
strain H37Rv and strain H37Ra
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
not all strains carry the gene pldA
-
-
Manually annotated by BRENDA team
castor bean
-
-
Manually annotated by BRENDA team
strain Madrid Evir, a virulent revertant of the attenuated Madrid E strain, gene pld
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
AA586
-
-
Manually annotated by BRENDA team
strain CS-57
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
elevated activity during early logarithmic growth phase
-
-
Manually annotated by BRENDA team
mung bean
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2R)-3-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}-2-({12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]dodecanoyl}oxy)propyl tetradecanoate + H2O
ethanolamine + (2R)-2-({12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]dodecanoyl}oxy)-3-(phosphonooxy)propyl tetradecanoate
show the reaction diagram
-
-
-
-
?
(7R)-4-hydroxy-N,N,N-trimethyl-7-({12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]dodecanoyl}oxy)-10-oxo-3,5,9-trioxa-4-phosphatricosan-1-aminium 4-oxide + H2O
choline + (2R)-2-({12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]dodecanoyl}oxy)-3-(phosphonooxy)propyl tetradecanoate
show the reaction diagram
-
-
-
-
?
1,2-dibutyl-sn-glycero-3-phosphocholine + H2O
choline + ?
show the reaction diagram
-
-
?
1,2-dihexanoyl-sn-glycero-3-phosphocholine + H2O
1,2-dihexanoyl-sn-glycero-3-phosphatidate + choline
show the reaction diagram
-
-
-
-
?
1,2-dioleoyl-sn-glycero-3-phosphocholine + glycerol
1,2-dioleoyl-sn-glycero-3-phospho-3'-sn-glycerol + 1,2-dioleoyl-sn-glycero-3-phospho-1'-sn-glycerol + choline
show the reaction diagram
1,2-dioleoyl-sn-glycerophosphocholine + 2-[bis(2-hydroxyethyl)imino]-2-(hydroxymethyl)-1,3-propanediol
choline + 1,2-dioleoyl-sn-glycerophospho-2-[bis(2-hydroxyethyl)imino]-2-(hydroxymethyl)-1,3-propanediol
show the reaction diagram
-
with BisTris as acceptor alcohol two regioisomeric forms of phosphatidyl-BisTris are obtained, product yield: 19.6% (regioisomer I), 3,1% (regioisomer II), purity of product: 98% (regioisomer I), 97% (regioisomer I)
-
-
?
1,2-dioleoyl-sn-glycerophosphocholine + diethanolamine
choline + 1,2-dioleoyl-sn-glycerophospho-diethanolamine
show the reaction diagram
1,2-dioleoyl-sn-glycerophosphocholine + diethanolamine
choline + bis(1,2-dioleoyl-sn-glycerophospho)-diethanolamine
show the reaction diagram
-
-
-
-
?
1,2-dioleoyl-sn-glycerophosphocholine + H2O
choline + 1,2-dioleoyl-sn-glycero-3-phosphatidic acid
show the reaction diagram
-
-
-
-
?
1,2-dioleoyl-sn-glycerophosphocholine + serinol
choline + 1,2-dioleoyl-sn-glycerophospho-serinol
show the reaction diagram
1,2-dioleoyl-sn-glycerophosphocholine + serinol
choline + bis(1,2-dioleoyl-sn-glycerophospho)-serinol
show the reaction diagram
-
-
-
-
?
1,2-dioleoyl-sn-glycerophosphocholine + triethanolamine
choline + 1,2-dioleoyl-sn-glycerophospho-triethanolamine
show the reaction diagram
1,2-dioleoyl-sn-glycerophosphocholine + triethanolamine
choline + bis(1,2-dioleoyl-sn-glycerophospho)-triethanolamine
show the reaction diagram
-
-
-
-
?
1,2-dioleoyl-sn-glycerophosphocholine + tris(hydroxymethyl)-aminomethane
choline + 1,2-dioleoyl-sn-glycerophospho-tris(hydroxymethyl)-aminomethane
show the reaction diagram
-
product yield: 31.6%, purity of product: 95%
-
-
?
1,2-dioleoyl-sn-glycerophosphocholine + tris(hydroxymethyl)-aminomethane
choline + bis(1,2-dioleoyl-sn-glycerophospho)-tris(hydroxymethyl)-aminomethane
show the reaction diagram
-
-
-
-
?
1-hexadecanoyl-2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)aminohexanoyl]-sn-glycero-3-phosphocholine + H2O
?
show the reaction diagram
-
fluorescent substrate
-
-
?
1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine + H2O
?
show the reaction diagram
1-O-alkyl-2-lyso-phosphatidylcholine + H2O
choline + 1-O-alkyl-2-lyso-phosphatidate
show the reaction diagram
-
-
-
-
?
1-O-octadecyl-sn-glycero-3-phosphocholine + H2O
1-O-octadecyl-sn-glycero-3-phosphatidate + choline
show the reaction diagram
-
-
-
-
?
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine + H2O
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidic acid + choline
show the reaction diagram
2-(13'-hydroperoxy-octadecadienoyl)-1-palmitoylglycero-phosphocholine + N,N,N-triethyl-N-2-hydroxyethylammonium bromide
?
show the reaction diagram
-
a synthetic phosphatidyl acceptor and substrate in transphosphatidylation reaction
-
-
?
2-(13'-hydroxy-octadecadienoyl)-1-palmitoylglycero-phosphocholine + N,N,N-triethyl-N-2-hydroxyethylammonium bromide
?
show the reaction diagram
-
a synthetic phosphatidyl acceptor and substrate in transphosphatidylation reaction
-
-
?
2-(13'-oxo-octadecadienoyl)-1-palmitoylglycero-phosphocholine + N,N,N-triethyl-N-2-hydroxyethylammonium bromide
?
show the reaction diagram
-
a synthetic phosphatidyl acceptor and substrate in transphosphatidylation reaction
-
-
?
2-decanoyl-1-(O-[(11-(4,4-difluoro-5,7-dimethyl)-4-bora-3a,4a-diaza-s-indacene-3-propionyl)amino]-undecyl)-phosphatidylcholine + H2O
2-decanoyl-1-(O-[(11-(4,4-difluoro-5,7-dimethyl)-4-bora-3a,4a-diaza-s-indacene-3-propionyl)amino]-undecyl)-phosphatidic acid + choline
show the reaction diagram
-
BODIPY-fluorophor-phosphatidylcholine as substrate
-
-
?
bis(4-nitrophenyl)phosphate + H2O
4-nitrophenol + phosphate
show the reaction diagram
-
-
-
?
bis(p-nitrophenyl)phosphate + H2O
?
show the reaction diagram
-
-
-
?
cardiolipin + H2O
sn-glycero-1-phosphate + diacylglycerophosphate
show the reaction diagram
dibutyroylphosphatidylcholine + H2O
dibutyroylglycerophosphate + choline
show the reaction diagram
-
-
-
-
?
diheptanoylphosphatidylcholine + H2O
diheptanoylglycerophosphate + choline
show the reaction diagram
-
-
-
-
?
dihexanoylphosphatidylcholine + H2O
dihexanoylglycerophosphate + choline
show the reaction diagram
dioleoyl-phosphatidylcholine + cyclohexane-1,2,3-triol
choline + dioleoyl-phosphatidylcyclohexane-2,3-diol
show the reaction diagram
in the cases of 1,2-diols, triols, and myo-inositol mutant W187F/Y191R generates the corresponding transphosphatidylated products more efficiently than wild-type
-
-
?
dioleoyl-phosphatidylcholine + cyclohexane-1,2,5-triol
choline + dioleoyl-phosphatidylcyclohexane-2,5-diol
show the reaction diagram
in the cases of 1,2-diols, triols, and myo-inositol mutant W187F/Y191R generates the corresponding transphosphatidylated products more efficiently than wild-type
-
-
?
dioleoyl-phosphatidylcholine + cyclohexane-1,2-diol
choline + dioleoyl-phosphatidylcyclohexane-2-ol
show the reaction diagram
in the cases of 1,2-diols, triols, and myo-inositol mutant W187F/Y191R generates the corresponding transphosphatidylated products more efficiently than wild-type
-
-
?
dioleoyl-phosphatidylcholine + cyclohexane-1,3-diol
choline + dioleoyl-phosphatidylcyclohexane-3-ol
show the reaction diagram
in the cases of 1,2-diols, triols, and myo-inositol mutant W187F/Y191R generates the corresponding transphosphatidylated products more efficiently than wild-type
-
-
?
dioleoyl-phosphatidylcholine + cyclohexane-1,4-diol
choline + dioleoyl-phosphatidylcyclohexane-4-ol
show the reaction diagram
-
-
-
?
dioleoyl-phosphatidylcholine + cyclohexanol
choline + dioleoyl-phosphatidylcyclohexane
show the reaction diagram
in the cases of cyclohexanol and of cyclohexane-1,4-diol, the wild-type enzyme generates the corresponding transphosphatidylated products more efficiently than the mutant W187F/Y191R
-
-
?
dioleoyl-phosphatidylcholine + H2O
choline + dioleoyl-phosphatidate
show the reaction diagram
-
-
-
?
dioleoyl-phosphatidylcholine + myo-inositol
?
show the reaction diagram
in the cases of 1,2-diols, triols, and myo-inositol mutant W187F/Y191R generates the corresponding transphosphatidylated products more efficiently than wild-type
-
-
?
dioleoyl-phosphatidylcholine + myo-inositol
phosphatidylinositol + choline
show the reaction diagram
dioleoylphosphatidylcholine + myo-inositol
choline + dioleoylphosphatidylinositol
show the reaction diagram
-
transphosphatidylation activity of mutant W187D/Y191Y/Y385R enzyme
-
-
?
dipalmitoyl phosphatidylcholine + H2O
choline + phosphatidate
show the reaction diagram
-
-
-
?
dipalmitoylphosphatidylcholine + H2O
1,2-dipalmitoylglycerophosphate + choline
show the reaction diagram
dipalmitoylphosphatidylcholine + H2O
dipalmitoylglycerophosphate + choline
show the reaction diagram
DNA + H2O
smaller DNA fragments
show the reaction diagram
glycerophospho-(N-palmitoyl)ethanolamine + H2O
N-palmitoylethanolamine + ?
show the reaction diagram
-
-
1% of the activity with N-palmitoyl-phosphatidylethanolamine
-
?
glycosylinositol phosphoceramide + H2O
phytoceramide-1-phosphate + glycosylinositol
show the reaction diagram
lysophosphatidylcholine + glycerol
?
show the reaction diagram
-
-
-
?
lysophosphatidylcholine + H2O
choline + lysophosphatidate
show the reaction diagram
-
about 20 times slower than reaction of phosphatidylcholine
-
?
lysophosphatidylcholine + H2O
choline + lysophosphatidic acid
show the reaction diagram
-
-
-
-
?
lysophosphatidylcholine + H2O
monoacylglycerophosphate + choline
show the reaction diagram
N-acyl-phosphatidylethanolamine + H2O
N-acylethanolamine + phosphatidate
show the reaction diagram
N-acylphosphatidylethanolamine + H2O
N-acylethanolamine + phosphatidate
show the reaction diagram
-
-
-
-
?
N-arachidonoyl-phosphatidylethanolamine + H2O
phosphatidic acid + N-arachidonoylethanolamine
show the reaction diagram
-
-
-
?
n-butanol + phosphatidylcholine
phosphatidylbutanol + choline
show the reaction diagram
-
-
-
-
?
N-lauroyl-phosphatidylethanolamine + H2O
phosphatidic acid + N-lauroylethanolamine
show the reaction diagram
N-palmitoyl-lyso-phosphatidylethanolamine + H2O
N-palmitoylethanolamine + sn-glycerol 3-phosphate
show the reaction diagram
-
-
4% of the activity with N-palmitoyl-phosphatidylethanolamine
-
?
N-palmitoyl-phosphatidylethanolamine + H2O
phosphatidic acid + N-palmitoylethanolamine
show the reaction diagram
octadecylphosphocholine + L-serine
octadecylphospho-L-serine + choline
show the reaction diagram
p-nitrophenylphosphorylcholine + H2O
?
show the reaction diagram
-
-
-
?
phosphatidyl-p-nitrophenol + H2O
phosphatidate + p-nitrophenol
show the reaction diagram
phosphatidyl-p-nitrophenol + H2O
phosphatidic acid + p-nitrophenol
show the reaction diagram
phosphatidylcholine + butanol
phosphatidylbutanol + choline
show the reaction diagram
phosphatidylcholine + D-arabinose
phosphatidylarabinose + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + D-fructose
phosphatidylfructose + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + D-galactose
phosphatidylgalactose + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + D-glucose
phosphatidylglucose + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + D-mannose
phosphatidylmannose + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + D-serine
phosphatidylserine + choline
show the reaction diagram
phosphatidylcholine + D-xylose
phosphatidylxylose + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + diethyleneglycol
phosphatidyldiethyleneglycol + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + diethyleneglycol monomethyl ester
diethyleneglycol dimethyl phosphatidic acid + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + ethanol
choline + phosphatidyl ethanol
show the reaction diagram
-
PLD also performs transphosphatidylation using ethanol as phosphatidyl acceptor
-
-
?
phosphatidylcholine + ethanol
choline + phosphatidylethanol
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + ethanol
phosphatidylethanol + choline
show the reaction diagram
phosphatidylcholine + ethanolamine
phosphatidylethanolamine + choline
show the reaction diagram
phosphatidylcholine + ethyleneglycol
phosphatidylethyleneglycol + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + ethyleneglycol monomethyl ester
ethyleneglycol monomethyl phosphatidic acid + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + glycerol
?
show the reaction diagram
-
-
-
?
phosphatidylcholine + glycerol
phosphatidylglycerol + choline
show the reaction diagram
phosphatidylcholine + H2O
1,2-diacylglycerophosphate + choline
show the reaction diagram
phosphatidylcholine + H2O
choline + ?
show the reaction diagram
phosphatidylcholine + H2O
choline + a phosphatidate
show the reaction diagram
-
phosphatidylcholine hydrolysis
-
-
?
phosphatidylcholine + H2O
choline + phosphatidate
show the reaction diagram
phosphatidylcholine + H2O
choline + phosphatidic acid
show the reaction diagram
phosphatidylcholine + H2O
phosphatidate + choline
show the reaction diagram
phosphatidylcholine + H2O
phosphatidic acid + choline
show the reaction diagram
phosphatidylcholine + heptanol
phosphatidylheptanol + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + hexanol
phosphatidylhexanol + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + inositol
phosphatidylinositol + choline
show the reaction diagram
phosphatidylcholine + L-serine
phosphatidyl-L-serine + choline
show the reaction diagram
-
-
-
?
phosphatidylcholine + L-serine
phosphatidylserine + choline
show the reaction diagram
phosphatidylcholine + L-sorbose
phosphatidylsorbose + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + methanol
phosphatidylmethanol + choline
show the reaction diagram
phosphatidylcholine + myo-inositol
phosphatidylinositol + choline
show the reaction diagram
the wild-type enzyme is capable of synthesizing phosphatidylinositol by transphosphatidylation. Increase in phosphatidylinositol yield is possible by providing excess of solvated myo-inositol, which is achievable at high temperatures due to its highly temperature-dependent solubility, especially by enzyme variants with increased thermostability, e.g. mutant W187D/Y191Y/Y385R
-
-
?
phosphatidylcholine + N,N,N-triethyl-N-2-hydroxyethylammonium bromide
choline + ?
show the reaction diagram
-
a synthetic phosphatidyl acceptor in transphosphatidylation reaction
-
-
?
phosphatidylcholine + pentanol
phosphatidylpentanol + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + propanol
phosphatidylpropanol + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + triethyleneglycol
phosphatidyltriethyleneglycol + choline
show the reaction diagram
-
-
-
-
?
phosphatidylcholine + triethyleneglycol monomethyl ester
triethyleneglycol trimethyl phosphatidic acid + choline
show the reaction diagram
-
-
-
-
?
phosphatidylethanolamine + H2O
1,2-diacylglycerophosphate + ethanolamine
show the reaction diagram
phosphatidylethanolamine + H2O
ethanolamine + phosphatidate
show the reaction diagram
phosphatidylethanolamine + H2O
ethanolamine + phosphatidic acid
show the reaction diagram
phosphatidylethanolamine + H2O
phosphatidate + ethanolamine
show the reaction diagram
phosphatidylglycerol + H2O
?
show the reaction diagram
-
-
-
?
phosphatidylglycerol + H2O
glycerol + 1,2-diacylglycerophosphate
show the reaction diagram
phosphatidylglycerol + H2O
glycerol + phosphatidate
show the reaction diagram
-
-
-
-
?
phosphatidylglycerol + H2O
glycerol + phosphatidic acid
show the reaction diagram
phosphatidylglycerol + H2O
phosphatidate + glycerol
show the reaction diagram
phosphatidylglycerol + H2O
sn-glycero-1-phosphate + diacylglycerophosphate
show the reaction diagram
phosphatidylinositol + H2O
1,2-diacylglycerophosphate + inositol
show the reaction diagram
phosphatidylinositol + H2O
phosphatidate + inositol
show the reaction diagram
phosphatidylserine + H2O
1,2-diacylglycerophosphate + serine
show the reaction diagram
phosphatidylserine + H2O
L-serine + phosphatidate
show the reaction diagram
phosphatidylserine + H2O
phosphatidate + serine
show the reaction diagram
phosphatidylserine + H2O
serine + phosphatidic acid
show the reaction diagram
phospholipid + alcohol
phospholipid + alcohol
show the reaction diagram
phospholipid + H2O
phosphatidic acid + alcohol
show the reaction diagram
sphingomyelin + H2O
N-acylsphingosylphosphate + choline
show the reaction diagram
additional information
?
-