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Literature summary for 3.5.1.99 extracted from

  • Patricelli, M.P.; Cravatt, B.F.
    Characterization and manipulation of the acyl chain selectivity of fatty acid amide hydrolase (2001), Biochemistry, 40, 6107-6115.
    View publication on PubMed
Search for more literature for 3.5.1.99

Protein Variants

Protein Variants Comment Organism
A487V kcat/Km for nonanoyl p-nitroanilide is 1.3fold higher than wild-type value, kcat/Km for myristoyl p-nitroanilide is 1.5fold lower than wild-type value, kcat/Km for oleoyl p-nitroanilide is 1.4fold lower than wild-type value Rattus norvegicus
G489A kcat/Km for nonanoyl p-nitroanilide is 3fold lower than wild-type value, kcat/Km for myristoyl p-nitroanilide is 1.9fold lower than wild-type value, kcat/Km for oleoyl p-nitroanilide is 1.4fold than wild-type value Rattus norvegicus
I491A mutant displays a greatly reduced binding affinity for medium-chain pNA substrates (7-12 carbons), kcat/Km for nonanoyl p-nitroanilide is 8.1fold lower than wild-type value, kcat/Km for myristoyl p-nitroanilide is identical to wild-type value, kcat/Km for oleoyl p-nitroanilide is 2.1fold lower than wild-type value Rattus norvegicus
T488A kcat/Km for nonanoyl p-nitroanilide is 2.8fold lower than wild-type value, kcat/Km for myristoyl p-nitroanilide is 1.4fold lower than wild-type value, kcat/Km for oleoyl p-nitroanilide is 1.6fold lower than wild-type value Rattus norvegicus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.057
-
 decanoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.057
-
 nonanoyl p-nitroanilide pH 9.0, mutant enzyme A487V Rattus norvegicus
0.06
-
 arachidonoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.065
-
 lauroyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.069
-
 myristoyl p-nitroanilide pH 9.0, mutant enzyme A487V Rattus norvegicus
0.072
-
 myristoyl p-nitroanilide pH 9.0, mutant enzyme I491A Rattus norvegicus
0.073
-
 nonanoyl p-nitroanilide pH 9.0, mutant enzyme G489A Rattus norvegicus
0.074
-
 oleoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.074
-
 nonanoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.074
-
 palmitoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.083
-
 oleoyl p-nitroanilide pH 9.0, mutant enzyme A487V Rattus norvegicus
0.092
-
 myristoyl p-nitroanilide pH 9.0, mutant enzyme T488A Rattus norvegicus
0.094
-
 myristoyl p-nitroanilide pH 9.0, mutant enzyme G489A Rattus norvegicus
0.095
-
 oleoyl p-nitroanilide pH 9.0, mutant enzyme T488A Rattus norvegicus
0.098
-
 oleoyl p-nitroanilide pH 9.0, mutant enzyme G489A Rattus norvegicus
0.099
-
 myristoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.126
-
 oleoyl p-nitroanilide pH 9.0, mutant enzyme I491A Rattus norvegicus
0.179
-
 nonanoyl p-nitroanilide pH 9.0, mutant enzyme T488A Rattus norvegicus
0.22
-
 octanoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.41
-
 heptanoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.57
-
 nonanoyl p-nitroanilide pH 9.0, mutant enzyme I491A Rattus norvegicus

Organism

Organism UniProt Comment Textmining
Rattus norvegicus
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
arachidonoyl p-nitroanilide + H2O
-
 Rattus norvegicus arachidonate + p-nitroaniline
-
 ?
decanoyl p-nitroanilide + H2O
-
 Rattus norvegicus decanoate + p-nitroaniline
-
 ?
heptanoyl p-nitroanilide + H2O
-
 Rattus norvegicus heptanoate + p-nitroaniline
-
 ?
lauroyl p-nitroanilide + H2O
-
 Rattus norvegicus laurate + p-nitroaniline
-
 ?
additional information catalytic efficiency (kcat/Km) of FAAH for nonanoyl p-nitroanilide is approximately 50fold higher than for hexanoyl p-nitroanilide. NAI491 participates in hydrophobic binding interactions with medium-chain FAAH substrates. Use of p-nitroanilide substrates allows for the precise monitoring of enzymatic hydrolysis rates by following the increase in UV absorbance at 382 nm due to the release of p-nitroaniline. p-Nitroanilides are slower FAAH substrates than the corresponding primary amides, however, the binding affinities of these two classes of substrates are equivalent. Due to the slower rates of p-nitroanilide hydrolysis relative to the corresponding primary amides, it can be assumed that pNA substrates are hydrolyzed by FAAH in an acylation rate-limiting manner, allowing for the direct measurement of substrate binding constants through the determination of Km values Rattus norvegicus ?
-
 ?
myristoyl p-nitroanilide + H2O
-
 Rattus norvegicus myristate + p-nitroaniline
-
 ?
nonanoyl p-nitroanilide + H2O
-
 Rattus norvegicus nonanoate + p-nitroaniline
-
 ?
octanoyl p-nitroanilide + H2O
-
 Rattus norvegicus octanoate + p-nitroaniline
-
 ?
oleoyl p-nitroanilide + H2O
-
 Rattus norvegicus oleate + p-nitroaniline
-
 ?
palmitoyl p-nitroanilide + H2O
-
 Rattus norvegicus palmitate + p-nitroaniline
-
 ?

Synonyms

Synonyms Comment Organism
FAAH
-
 Rattus norvegicus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.13
-
 myristoyl p-nitroanilide pH 9.0, mutant enzyme A487V Rattus norvegicus
0.14
-
 myristoyl p-nitroanilide pH 9.0, mutant enzyme G489A Rattus norvegicus
0.19
-
 myristoyl p-nitroanilide pH 9.0, mutant enzyme T488A Rattus norvegicus
0.2
-
 nonanoyl p-nitroanilide pH 9.0, mutant enzyme G489A Rattus norvegicus
0.21
-
 oleoyl p-nitroanilide pH 9.0, mutant enzyme A487V Rattus norvegicus
0.21
-
 myristoyl p-nitroanilide pH 9.0, mutant enzyme I491A Rattus norvegicus
0.21
-
 oleoyl p-nitroanilide pH 9.0, mutant enzyme T488A Rattus norvegicus
0.22
-
 oleoyl p-nitroanilide pH 9.0, mutant enzyme I491A Rattus norvegicus
0.25
-
 oleoyl p-nitroanilide pH 9.0, mutant enzyme G489A Rattus norvegicus
0.27
-
 oleoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.27
-
 palmitoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.29
-
 myristoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.46
-
 heptanoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.46
-
 lauroyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.48
-
 arachidonoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.51
-
 nonanoyl p-nitroanilide pH 9.0, mutant enzyme T488A Rattus norvegicus
0.56
-
 decanoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.58
-
 nonanoyl p-nitroanilide pH 9.0, mutant enzyme I491A Rattus norvegicus
0.6
-
 nonanoyl p-nitroanilide pH 9.0, mutant enzyme A487V Rattus norvegicus
0.6
-
 nonanoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus
0.73
-
 octanoyl p-nitroanilide pH 9.0, wild-type enzyme Rattus norvegicus