6.2.1.2: medium-chain acyl-CoA ligase
This is an abbreviated version!
For detailed information about medium-chain acyl-CoA ligase, go to the full flat file.
Word Map on EC 6.2.1.2
-
6.2.1.2
-
desaturase
-
polyunsaturated
-
pufas
-
docosahexaenoic
-
arachidonic
-
monounsaturated
-
eicosapentaenoic
-
linoleic
-
desaturation
-
elovl5
-
unsaturated
-
lc-pufas
-
acyl-coas
-
oleic
-
stearoyl-coa
-
very-long-chain
-
vlcfas
-
palmitoleic
-
delta6
-
stearic
-
alpha-linolenic
-
linseed
-
gamma-linolenic
-
alpina
-
stargardt
-
mortierella
-
isochrysis
-
3-ketoacyl-coa
-
erucic
-
cis-vaccenic
-
vaccenic
-
dihomo-gamma-linolenic
-
medicine
-
stearidonic
- 6.2.1.2
-
desaturase
-
polyunsaturated
-
pufas
-
docosahexaenoic
-
arachidonic
-
monounsaturated
-
eicosapentaenoic
-
linoleic
-
desaturation
- elovl5
- unsaturated
-
lc-pufas
- acyl-coas
-
oleic
- stearoyl-coa
-
very-long-chain
-
vlcfas
-
palmitoleic
-
delta6
-
stearic
-
alpha-linolenic
-
linseed
-
gamma-linolenic
- alpina
- stargardt
- mortierella
- isochrysis
- 3-ketoacyl-coa
-
erucic
-
cis-vaccenic
-
vaccenic
-
dihomo-gamma-linolenic
- medicine
-
stearidonic
Reaction
Synonyms
Acyl-activating enzyme, butanoate:CoA ligase (AMP-forming), butyrate-CoA ligase, Butyryl-CoA synthetase, Butyryl-coenzyme A synthetase, EloA, elongase, Fatty acid thiokinase (medium chain), L-(+)-3-Hydroxybutyryl CoA ligase, Macs, MACS2, medium chain acyl-CoA synthase, medium chain acyl-CoA synthetase, Medium chain acyl-coenzyme A synthetase, medium-chain acyl coenzyme A synthetase, medium-chain acyl-CoA synthetase 2, Mig protein, More, Short-chain acyl-CoA synthetase, Synthetase, butyryl conzyme A, xenobiotic/medium-chain fatty acid:CoA ligase, XM-ligase
ECTree
6.2.1.2 medium-chain acyl-CoA ligaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 6.2.1.2 - medium-chain acyl-CoA ligase
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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
ATP + 1-anthracenecarboxylic acid + CoA
AMP + diphosphate + anthracene-1-carboxyl-CoA
-
2% of the activity with hexanoic acid
-
?
ATP + 2-aminobenzoate + CoA
AMP + diphosphate + 2-aminobenzoyl-CoA
-
1.4% of the activity with dodecanoate
-
?
ATP + 2-anthracenecarboxylic acid + CoA
AMP + diphosphate + anthracene-2-carboxyl-CoA
-
16% of the activity with hexanoic acid
-
?
ATP + 3,4-methylenedioxycinnamic acid + CoA
AMP + diphosphate + 3,4-methylenedioxy-cinnamoyl-CoA
high activity
-
-
?
ATP + 3-ethoxycinnamic acid + CoA
AMP + diphosphate + 3-ethoxy-cinnamoyl-CoA
high activity
-
-
?
ATP + 3-methoxycinnamic acid + CoA
AMP + diphosphate + 3-methoxy-cinnamoyl-CoA
high activity
-
-
?
ATP + 3-nitrobenzoate + CoA
AMP + diphosphate + 3-nitrobenzoyl-CoA
-
28% of the activity with benzoate
-
?
ATP + 4-heptylbenzoate + CoA
AMP + diphosphate + 4-heptylbenzoyl-CoA
-
66% of the activity with hexanoic acid
-
?
ATP + 4-nitrobenzoate + CoA
AMP + diphosphate + 4-nitrobenzoyl-CoA
-
29% of the activity with benzoate
-
?
ATP + a medium chain fatty acid or an aromatic acid or an arylacetic acid + CoA
?
-
the enzyme catalyzes the first reaction of glycine conjugation, which is an important route of detoxification of many xenobiotic and endogenous carboxylic acids
-
-
?
ATP + arachidonic acid + CoA
AMP + diphosphate + arachidonoyl-CoA
-
5.2% of the activity with dodecanoate
-
?
ATP + benzoic acid + CoA
AMP + diphosphate + benzoyl-CoA
-
also active with several benzoic acids substituted at position 2, 3 or 4
-
-
?
ATP + caproic acid + CoA
AMP + diphosphate + caproyl-CoA
-
-
-
?
ATP + crotonate + CoA
AMP + diphosphate + crotonyl-CoA
-
i.e. E-2-butenoate, 20% of the activity relative to butyrate
-
-
?
ATP + cyclohexanoic acid + CoA
AMP + diphosphate + cyclohexanoyl-CoA
-
41% of the activity with hexanoic acid
-
?
ATP + L-(+)-3-hydroxybutyrate + CoA
?
-
enzyme reesterifies CoA and L-(+)-3-hydroxybutyrate. It is required for the production of L-(+)-3-hydroxybutyrate in rat liver
-
-
?
ATP + L-(+)-3-hydroxybutyrate + CoA
AMP + diphosphate + L-(+)-3-hydroxybutyryl-CoA
-
-
-
?
ATP + laurate + CoA
AMP + diphosphate + lauroyl-CoA
-
12.6% of the activity with octanoate
-
?
ATP + linolenic acid + CoA
AMP + diphosphate + linolenoyl-CoA
-
8.3% of the activity with dodecanoate
-
?
ATP + m-hydroxybenzoate + CoA
AMP + diphosphate + m-hydroxybenzoyl-CoA
-
0.8% of the activity with dodecanoate
-
?
ATP + myristic acid + CoA
AMP + diphosphate + myristoyl-CoA
-
-
-
?
ATP + phenoxyacetate + CoA
AMP + diphosphate + phenoxyacetyl-CoA
i.e. POA, low activity
-
-
?
ATP + propionic acid + CoA
AMP + diphosphate + propionyl-CoA
low activity
-
-
?
ATP + tetradecanoate + CoA
AMP + diphosphate + tetradecanoyl-CoA
-
3.9% of the activity with dodecanoate
-
?
ATP + trans-4-coumaric acid + CoA
AMP + diphosphate + trans-4-coumaroyl-CoA
-
-
-
?
ATP + trans-cinnamic acid + CoA
AMP + diphosphate + trans-cinnamoyl-CoA
1000fold higher activity compared to PAA
-
-
?
ATP + tridecanoate + CoA
AMP + diphosphate + tridecanoyl-CoA
-
15% of the activity with dodecanoate
-
?
ATP + valerate + CoA
AMP + diphosphate + valeryl-CoA
-
9.9% of the activity with octanoate
-
?
ATP + 1-naphthoic acid + CoA
AMP + diphosphate + 1-naphthoyl-CoA
-
3% of the activity with hexanoic acid
-
?
ATP + 1-naphthoic acid + CoA
AMP + diphosphate + 1-naphthoyl-CoA
-
less than 10% of the activity with hexanoic acid
-
?
ATP + 1-naphthylacetic acid + CoA
AMP + diphosphate + 1-naphthyl-acetyl-CoA
-
18% of the activity with hexanoic acid
-
?
ATP + 1-naphthylacetic acid + CoA
AMP + diphosphate + 1-naphthyl-acetyl-CoA
-
about 25% of the activity with hexanoic acid
-
?
ATP + 1-naphthylacetic acid + CoA
AMP + diphosphate + 1-naphthylacetoyl-CoA
-
-
-
-
?
ATP + 1-naphthylacetic acid + CoA
AMP + diphosphate + 1-naphthylacetoyl-CoA
-
-
-
-
?
ATP + 2-methylbutyrate + CoA
AMP + diphosphate + 2-methylbutyryl-CoA
when propionate or other less favorable acyl substrates, such as butyrate, 2-methylpropionate, or 2-methylvalerate, are utilized, the acyl-CoA is not produced or is produced at reduced levels. Instead, acyl-AMP and diphosphate are released in the absence of CoA, whereas in the presence of CoA, the intermediate is broken down into AMP and the acyl substrate, which are released along with diphosphate. These results suggest that although acyl-CoA synthetases may have the ability to utilize a broad range of substrates for the acyl-adenylate-forming first step of the reaction, the intermediate may not be suitable for the thioester-forming second step
-
-
?
ATP + 2-methylbutyrate + CoA
AMP + diphosphate + 2-methylbutyryl-CoA
when propionate or other less favorable acyl substrates, such as butyrate, 2-methylpropionate, or 2-methylvalerate, are utilized, the acyl-CoA is not produced or is produced at reduced levels. Instead, acyl-AMP and diphosphate are released in the absence of CoA, whereas in the presence of CoA, the intermediate is broken down into AMP and the acyl substrate, which are released along with diphosphate. These results suggest that although acyl-CoA synthetases may have the ability to utilize a broad range of substrates for the acyl-adenylate-forming first step of the reaction, the intermediate may not be suitable for the thioester-forming second step
-
-
?
ATP + 2-naphthylacetic acid + CoA
AMP + diphosphate + 2-naphthyl-acetyl-CoA
-
21% of the activity with hexanoic acid
-
?
ATP + 2-naphthylacetic acid + CoA
AMP + diphosphate + 2-naphthyl-acetyl-CoA
-
about 35% of the activity with hexanoic acid
-
?
ATP + 3-aminobenzoate + CoA
AMP + diphosphate + 3-aminobenzoyl-CoA
-
5% of the activity with hexanoic acid
-
?
ATP + 3-aminobenzoate + CoA
AMP + diphosphate + 3-aminobenzoyl-CoA
-
29% of the activity with benzoate
-
?
ATP + 3-chlorobenzoate + CoA
AMP + diphosphate + 3-chlorobenzoyl-CoA
-
12% of the activity with hexanoic acid
-
?
ATP + 3-chlorobenzoate + CoA
AMP + diphosphate + 3-chlorobenzoyl-CoA
-
126% of the activity with benzoate
-
?
ATP + 3-methoxybenzoate + CoA
AMP + diphosphate + 3-methoxybenzoyl-CoA
-
48% of the activity with hexanoic acid
-
?
ATP + 3-methoxybenzoate + CoA
AMP + diphosphate + 3-methoxybenzoyl-CoA
-
54% of the activity with benzoate
-
?
ATP + 3-methylbenzoate + CoA
AMP + diphosphate + 3-methylbenzoyl-CoA
-
23% of the activity with hexanoic acid
-
?
ATP + 3-methylbenzoate + CoA
AMP + diphosphate + 3-methylbenzoyl-CoA
-
138% of the activity with benzoate
-
?
ATP + 4-aminobenzoate + CoA
AMP + diphosphate + 4-aminobenzoyl-CoA
-
3% of the activity with hexanoic acid
-
?
ATP + 4-aminobenzoate + CoA
AMP + diphosphate + 4-aminobenzoyl-CoA
-
19% of the activity with benzoate
-
?
ATP + 4-chlorobenzoate + CoA
AMP + diphosphate + 4-chlorobenzoyl-CoA
-
17% of the activity with hexanoic acid
-
?
ATP + 4-chlorobenzoate + CoA
AMP + diphosphate + 4-chlorobenzoyl-CoA
-
96% of the activity with benzoate
-
?
ATP + 4-methoxybenzoate + CoA
AMP + diphosphate + 4-methoxybenzoyl-CoA
-
47% of the activity with hexanoic acid
-
?
ATP + 4-methoxybenzoate + CoA
AMP + diphosphate + 4-methoxybenzoyl-CoA
-
43% of the activity with benzoate
-
?
ATP + 4-methylbenzoate + CoA
AMP + diphosphate + 4-methylbenzoyl-CoA
-
59% of the activity with hexanoic acid
-
?
ATP + 4-methylbenzoate + CoA
AMP + diphosphate + 4-methylbenzoyl-CoA
-
114% of the activity with benzoate
-
?
ATP + benzoate + CoA
AMP + diphosphate + benzoyl-CoA
-
19% of the activity with hexanoic acid
-
?
ATP + benzoate + CoA
AMP + diphosphate + benzoyl-CoA
-
bi uni uni bi ping pong mechanism with ATP binding first, followed in order by benzoate binding, diphosphate release, CoA binding, benzoyl-CoA release and AMP release
-
?
ATP + benzoate + CoA
AMP + diphosphate + benzoyl-CoA
-
high activities are obtained with benzoate having methyl, pentyl, and methoxy groups in the para- or meta-positions of the benzene ring
-
-
?
ATP + benzoate + CoA
AMP + diphosphate + benzoyl-CoA
-
about 30% of the activity with hexanoic acid
-
?
ATP + benzoate + CoA
AMP + diphosphate + benzoyl-CoA
-
high activities are obtained with benzoate having methyl, pentyl, and methoxy groups in the para- or meta-positions of the benzene ring
-
-
?
ATP + benzoate + CoA
AMP + diphosphate + benzoyl-CoA
-
2.3% of the activity with dodecanoate
-
?
ATP + benzoate + CoA
AMP + diphosphate + benzoyl-CoA
-
0.3% of the activity with octanoate
-
?
ATP + butyrate + CoA
AMP + diphosphate + butyryl-CoA
-
46% of the activity with octanoate
-
?
ATP + decanoate + CoA
AMP + diphosphate + decanoyl-CoA
-
substrate with the highest activity
-
?
ATP + decanoate + CoA
AMP + diphosphate + decanoyl-CoA
-
48% of the activity with octanoate
-
?
ATP + dodecanoate + CoA
AMP + diphosphate + dodecanoyl-CoA
-
39% of the activity with hexanoic acid
-
?
ATP + dodecanoate + CoA
AMP + diphosphate + dodecanoyl-CoA
-
31% of the activity with dodecanoate
-
?
ATP + heptanoate + CoA
AMP + diphosphate + heptanoyl-CoA
-
34% of the activity with dodecanoate
-
?
ATP + hexanoate + CoA
AMP + diphosphate + hexanoyl-CoA
-
maximal activity on hexanoate
-
-
?
ATP + hexanoate + CoA
AMP + diphosphate + hexanoyl-CoA
-
15% of the activity with octanoate
-
?
ATP + hexanoate + CoA
AMP + diphosphate + hexanoyl-CoA
-
maximal activity on hexanoate
-
-
?
ATP + hexanoate + CoA
AMP + diphosphate + hexanoyl-CoA
-
35% of the activity with dodecanoate
-
?
ATP + hexanoate + CoA
AMP + diphosphate + hexanoyl-CoA
-
15% of the activity with octanoate
-
?
ATP + indomethacin + CoA
AMP + diphosphate + ?
-
6% of the activity with hexanoic acid
-
?
ATP + indomethacin + CoA
AMP + diphosphate + ?
-
less than 5% of the activity with hexanoic acid
-
?
ATP + isobutyrate + CoA
AMP + diphosphate + isobutyryl-CoA
-
20% of the activity relative to butyrate
-
-
?
ATP + m-methoxybenzoate + CoA
AMP + diphosphate + m-methoxybenzoyl-CoA
-
-
-
-
?
ATP + octanoate + CoA
AMP + diphosphate + octanoyl-CoA
-
about 50% of the activity with hexanoic acid
-
?
ATP + octanoate + CoA
AMP + diphosphate + octanoyl-CoA
-
31% of the activity with dodecanoate
-
?
ATP + p-methoxybenzoate + CoA
AMP + diphosphate + p-methoxybenzoyl-CoA
-
-
-
-
?
ATP + pentanoate + CoA
AMP + diphosphate + pentanoyl-CoA
-
1.6% of the activity with dodecanoate
-
?
ATP + phenylacetate + CoA
AMP + diphosphate + phenylacetyl-CoA
enzymatic activation of phenylacetic acid to phenylacetyl-CoA is an important step in the biosynthesis of the beta-lactam antibiotic penicillin G by the fungus Penicillium chrysogenum, CoA esters of PAA and phenoxyacetic acid act as acyl donor in the exchange of the aminoadipyl side chain of isopenicillin N to produce penicillin G or penicillin V
-
-
?
ATP + phenylacetate + CoA
AMP + diphosphate + phenylacetyl-CoA
i.e. PAA
-
-
?
ATP + propionate + CoA
AMP + diphosphate + propionyl-CoA
-
2% of the activity with octanoate
-
?
ATP + tranexamic acid + CoA
AMP + diphosphate + tranexoyl-CoA
-
7% of the activity with hexanoic acid
-
?
ATP + tranexamic acid + CoA
AMP + diphosphate + tranexoyl-CoA
-
less than 10% of the activity with hexanoic acid
-
?
ATP + valproate + CoA
ADP + diphosphate + valproyl-CoA
-
less active on valproate
-
-
?
ATP + valproate + CoA
ADP + diphosphate + valproyl-CoA
-
less active on valproate
-
-
?
ATP + valproic acid + CoA
AMP + diphosphate + valproyl-CoA
-
less than 10% of the activity with hexanoic acid
-
?
ATP + valproic acid + CoA
AMP + diphosphate + valproyl-CoA
-
i.e. 2-n-propylpentanoic acid
-
-
?
additional information
?
-
-
straight chain acids having 3, 5 or 6 carbons are less active as substrates than butyrate
-
-
?
additional information
?
-
-
major enzyme for glycine conjugation of benzoic acids with electron-donating groups in bovine liver mitochondria
-
-
?
additional information
?
-
-
the enzyme catalyzes the first reaction of glycine conjugation
-
?
additional information
?
-
-
the enzyme is responsible for glycine conjugation
-
?
additional information
?
-
-
the enzyme is involved in the metabolism of fatty acid during mycobacterial survival in macrophages
-
?
additional information
?
-
Paecilomyces variotii AHU 9417
-
no activity with acetate and octanoate
-
-
?
additional information
?
-
the enzyme also belongs to EC 6.2.1.30, substrate specificity, the more substituted compounds ferulic acid, caffeic acid and sinapic acid, which are substrates for most 4-coumarate CoA ligases, are very poor substrates for the enzyme. With the exception of acetic acid, all short and medium chain fatty acids tested are converted by the enzyme, the enzyme is able to activate all the side chains of these naturally occurring lactam side products, overview. Residues H265, I266, Y267, V270, F307, F335, G337, A338, G361, T369, V370, and K557 are involved in substrate binding
-
-
?
