Information on EC 2.3.1.21 - carnitine O-palmitoyltransferase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY hide
2.3.1.21
-
RECOMMENDED NAME
GeneOntology No.
carnitine O-palmitoyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
palmitoyl-CoA + L-carnitine = CoA + L-palmitoylcarnitine
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
carnitine metabolism
-
-
Fatty acid degradation
-
-
mitochondrial L-carnitine shuttle
-
-
SYSTEMATIC NAME
IUBMB Comments
palmitoyl-CoA:L-carnitine O-palmitoyltransferase
Broad specificity to acyl group, over the range C8 to C18; optimal activity with palmitoyl-CoA. cf. EC 2.3.1.7 carnitine O-acetyltransferase and EC 2.3.1.137 carnitine O-octanoyltransferase.
CAS REGISTRY NUMBER
COMMENTARY hide
9068-41-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
embryo
-
-
Manually annotated by BRENDA team
2 isoforms L-CPT I and M-CPT I
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6J
C57BL/6J mice
-
-
Manually annotated by BRENDA team
no activity in Pichia pastoris
-
-
-
Manually annotated by BRENDA team
2 isoforms CPTo (I) and CPTi (II)
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Valanga nigricornis
Burm., grasshopper
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4,8-dimethylnonanoyl-CoA + L-carnitine
CoA + 4,8-dimethylnonanoyl-L-carnitine
show the reaction diagram
-
-
-
?
acyl-CoA + L-carnitine
CoA + L-acylcarnitine
show the reaction diagram
arachidoyl-CoA + L-carnitine
CoA + L-arachidoylcarnitine
show the reaction diagram
-
-
-
-
?
butyryl-CoA + L-carnitine
CoA + L-butyrylcarnitine
show the reaction diagram
decanoyl-CoA + L-carnitine
CoA + L-decanoylcarnitine
show the reaction diagram
docosanhexaenoyl-CoA + L-carnitine
CoA + L-docosanhexaenoylcarnitine
show the reaction diagram
-
-
-
-
?
dodecanoyl-CoA + L-carnitine
CoA + L-dodecanoylcarnitine
show the reaction diagram
-
-
-
?
erucoyl-CoA + L-carnitine
CoA + L-erucoylcarnitine
show the reaction diagram
-
-
-
-
?
hexanoyl-CoA + L-carnitine
CoA + L-hexanoylcarnitine
show the reaction diagram
L-carnitine + palmitoyl-CoA
L-palmitoylcarnitine + CoA
show the reaction diagram
lauroyl-CoA + L-carnitine
CoA + L-lauroylcarnitine
show the reaction diagram
linoleoyl-CoA + L-carnitine
CoA + L-linoleoylcarnitine
show the reaction diagram
myristoyl-CoA + L-carnitine
CoA + L-myristoylcarnitine
show the reaction diagram
octanoyl-CoA + L-carnitine
CoA + L-octanoylcarnitine
show the reaction diagram
oleoyl-CoA + L-carnitine
CoA + L-oleoylcarnitine
show the reaction diagram
palmitoleoyl-CoA + L-carnitine
CoA + L-palmitoleoylcarnitine
show the reaction diagram
-
activity is 47% higher than with palmitoyl-CoA
-
-
?
palmitoyl-CoA + DL-carnitine
CoA + DL-palmitoylcarnitine
show the reaction diagram
-
-
-
r
palmitoyl-CoA + L-carnitine
CoA + L-palmitoylcarnitine
show the reaction diagram
palmitoyl-CoA + L-carnitine
L-palmitoylcarnitine + CoA
show the reaction diagram
-
forward reaction by CPT I and reverse reaction by CPT II
-
r
stearoyl-CoA + L-carnitine
CoA + L-stearoylcarnitine
show the reaction diagram
trans-2-hexadecenoyl-CoA + L-carnitine
CoA + trans-2-hexadecenoyl-L-carnitine
show the reaction diagram
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
acyl-CoA + L-carnitine
CoA + L-acylcarnitine
show the reaction diagram
palmitoyl-CoA + L-carnitine
CoA + L-palmitoylcarnitine
show the reaction diagram
palmitoyl-CoA + L-carnitine
L-palmitoylcarnitine + CoA
show the reaction diagram
-
forward reaction by CPT I and reverse reaction by CPT II
-
r
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
11-trimethylamino-undecanoyl-DL-carnitine
-
-
-
2-bromoacetyl-CoA
-
-
2-Bromopalmitoyl-CoA
2-[5(4-Chlorophenyl)pentyl]-oxirane-2-carboxyl-CoA
-
-
4-hydroxy phenylglyoxylate
-
CPT I, greatly reduced inhibition of protease treated enzyme
acetyl-CoA
Bile acids
-
e.g. in cholestatic rats
Bromoacetyl-CoA
-
-
C75-CoA
cardiolipin
-
inhibits conversion of palmitoylcarnitine to palmitoyl-CoA, stimulates palmitoylcarnitine formation
carnitine
-
CPT I, slightly
chenodeoxycholic acid
-
competitive to carnitine
cholate
-
only CPTo
CoA esters of certain oxirane carboxylic acids
deoxycarnitine
-
-
diethyl dicarbonate
-
CPT II, strong, linear pseudo-first order kinetic, modification of a histidine residue, reversible by hydroxylamine, decanoyl-CoA and L-carnitine
Digitonin
-
CPTo and slightly CPTi
dinitrophenyl analogue of etomoxir
-
i.e. 2[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylic acid, DNP-Et, specific inhibitor for liver L-CPT I, identical with the small isoform of heart CPT I, complete inhibition of L-CPT I, but not M-CPT I
etomoxir
Etomoxir-CoA
-
CPTo
Etomoxiryl-CoA
gamma-linolenic acid
-
inhibits CPT I in vivo and reduces malonyl-CoA sensitivity, decreases affinity for 16:0 acyl-CoA substrate
Hemipalmitoylcarnitinium bromide
L-aminocarnitine
L-palmitoylcarnitine
-
competitive product inhibition
L-sulfocarnitine
-
ability to act as substrate or inhibitor of CPT is dependent on the nature of CPT and on the chain length of the acyl-CoA cosubstrate
malonyl-CoA
methylmalonyl-CoA
nagarse
-
mitochondria, malonyl-CoA protects
-
octyl glucoside
octyl-glucoside
-
-
oxfenicine
palmitoyl-CoA
palmitoylcarnitine
-
-
Palmitoylcholine
-
competitive in the forward reaction to both substrates
phosphatidylcholine
-
-
propionyl-CoA
-
CPT I, inhibition is not affected by proteinase treatment
Ro 25-0187
-
CPT I, strong, inhibitory effect is drastically reduced by protease treatment of outer mitochondrial membrane; malonyl-CoA analogue
S-(4-Bromo-2,3-dioxobutyl)-CoA
-
inhibition of malonyl-CoA sensitive enzyme, malonyl-CoA insensitive enzyme is not inhibited
Short chain-length fatty acylcarnitine derivatives
-
-
-
succinyl-CoA
-
partial proteolysis of CPT I slightly diminishes the inhibitory effect
Tetradecylglycidyl-CoA
thiolcarnitine
-
ability to act as substrate or inhibitor of CPT is dependent on the nature of CPT and on chain length of the acyl-CoA cosubstrate
trans-2-hexadecenoyl-CoA
competitive
Triton X-100
Trypsin
Tween 20
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
carbacyclin
cardiolipin
-
inhibits conversion of palmitoylcarnitine to palmitoyl-CoA, stimulates palmitoylcarnitine formation
cholate
-
activates only CPTi
daidzein
di(2-ethyl-hexyl)phtalate
-
-
genistein
L-carnitine
liothyronine
-
-
octyl glucoside
-
only CPTi
palmitoylcarnitine
-
high above micellar concentrations increase conversion of palmitoylcarnitine to palmitoyl-CoA by facilitating the removal of palmitoyl-CoA from the enzyme surface
PGC-1beta
-
peroxisome proliferator activated receptor gamma coactivator
-
Phosphatidylcholine liposomes
Phospholipids
-
e.g. phosphatidylcholine, cardiolipin, stimulate
Proteins
-
e.g. albumin, fatty acid-binding protein, lambda-globulin, stimulate
-
salicylic acid
-
activates best at 20 mM, pH changes
Triton X-100
-
only CPTi
Tween 20
additional information
-
clofibrate induces the enzyme expression in transfected Huh-7 cells
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.022
acetyl-CoA
-
-
0.0051 - 0.03
Butyryl-CoA
0.0055
CoA
-
-
0.0009 - 0.017
decanoyl-CoA
0.004
Dodecanoyl-CoA
-
-
0.0018 - 0.152
Hexanoyl-CoA
0.0017 - 127
L-carnitine
1.139
L-octanoylcarnitine
-
-
0.123 - 0.14
L-palmitoylcarnitine
0.011 - 0.013
Lauroyl-CoA
0.0012 - 0.031
myristoyl-CoA
0.0085 - 0.023
Octanoyl-CoA
0.0008 - 25.35
palmitoyl-CoA
0.0017 - 0.018
stearoyl-CoA
0.0081
trans-2-hexadecenoyl-CoA
pH 7.4, 37C
additional information
additional information
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.2
11-trimethylamino-undecanoyl-DL-carnitine
-
-
-
0.9
2-bromoacetyl-CoA
-
-
0.00066
2-Bromopalmitoyl-CoA
-
-
0.045
acetyl-CoA
-
-
0.6
chenodeoxycholic acid
-
-
0.045
CoA
-
-
0.0016 - 0.0215
Hemipalmitoylcarnitinium bromide
0.0035
L-aminocarnitine
-
CPT II
0.00022 - 0.17
malonyl-CoA
15
octyl-glucoside
-
with octanoyl-CoA as substrate
0.009 - 0.014
palmitoylcarnitine
0.0104 - 0.019
Palmitoylcholine
0.0188
trans-2-hexadecenoyl-CoA
pH 7.4, 37C
additional information
additional information
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00004 - 0.0007
C75-CoA
0.000015 - 0.0041
Etomoxiryl-CoA
0.00003 - 0.319
malonyl-CoA
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00035
-
transfected HEK-293T cell
0.0006
hepatocytes transduced with adenovirus encoding beta-galctosidase exposed to exogenous palmitate, measurement of CPT-1 activity at the end of the incubation period; hepatocytes transduced with adenovirus encoding beta-galctosidase exposed to exogenous palmitate, measurement of CPT-1 activity at the end of the incubation period
0.00062
F352C/V368I/V605L mutant protein, COS-7 cell lysate
0.00063
wild-type protein and F352C/V368I/V605L mutant protein, COS-7 cell lysate (doubly transfected)
0.00071
P504L/V605L mutant protein, COS-7 cell lysate
0.00072
F352C/V368I mutant protein, COS-7 cell lysate; wild-type protein and P504L/V605L mutant protein, COS-7 cell lysate (doubly transfected)
0.00073
F352C mutant protein, COS-7 cell lysate
0.00076
P504L mutant protein, COS-7 cell lysate
0.00078