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EC Tree
IUBMB Comments S-Benzyl-L-cysteine and, in decreasing order of activity, S-butyl-L-cysteine, S-propyl-L-cysteine, O-benzyl-L-serine and S-ethyl-L-cysteine, can act as acceptors.
The enzyme appears in viruses and cellular organisms
Synonyms
cysteine-s-conjugate n-acetyltransferase,
more
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acetyltransferase, cysteine S-conjugate N-
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acetyl-CoA + an L-cysteine-S-conjugate = CoA + an N-acetyl-L-cysteine-S-conjugate
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Acyl group transfer
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acetyl-CoA:S-substituted L-cysteine N-acetyltransferase
S-Benzyl-L-cysteine and, in decreasing order of activity, S-butyl-L-cysteine, S-propyl-L-cysteine, O-benzyl-L-serine and S-ethyl-L-cysteine, can act as acceptors.
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acetyl-CoA + an S-substituted L-cysteine
CoA + an S-substituted N-acetyl-L-cysteine
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final reaction of mercapturic biosynthesis
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?
acetyl-CoA + leukotriene E4
CoA + N-acetyl-leukotriene E4
about 1% of the activity with S-benzyl-L-cysteine
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?
acetyl-CoA + O-benzyl-L-serine
CoA + N-acetyl-O-benzyl-L-cysteine
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?
acetyl-CoA + S-1-menaphthyl-L-cysteine
CoA + N-acetyl-S-1-menaphthyl-L-cysteine
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?
acetyl-CoA + S-4-nitrobenzyl-L-cysteine
CoA + ?
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?
acetyl-CoA + S-4-nitrobenzyl-L-cysteine
CoA + N-acetyl-S-4-nitrobenzyl-L-cysteine
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?
acetyl-CoA + S-benzyl-L-cysteine
CoA + N-acetyl-S-benzyl-L-cysteine
acetyl-CoA + S-butyl-L-cysteine
CoA + N-acetyl-S-butyl-L-cysteine
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?
acetyl-CoA + S-ethyl-L-cysteine
CoA + N-acetyl-S-ethyl-L-cysteine
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?
acetyl-CoA + S-propyl-L-cysteine
CoA + N-acetyl-S-propyl-L-cysteine
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?
S-(1,2,3,4,4-pentachloro-butadienyl)-L-cysteine + acetyl-CoA
N-acetyl-S-(1,2,3,4,4-pentachlorobutadienyl)-L-cysteine + CoA
additional information
?
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acetyl-CoA + S-benzyl-L-cysteine
CoA + N-acetyl-S-benzyl-L-cysteine
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?
acetyl-CoA + S-benzyl-L-cysteine
CoA + N-acetyl-S-benzyl-L-cysteine
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best substrate
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?
S-(1,2,3,4,4-pentachloro-butadienyl)-L-cysteine + acetyl-CoA
N-acetyl-S-(1,2,3,4,4-pentachlorobutadienyl)-L-cysteine + CoA
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?
S-(1,2,3,4,4-pentachloro-butadienyl)-L-cysteine + acetyl-CoA
N-acetyl-S-(1,2,3,4,4-pentachlorobutadienyl)-L-cysteine + CoA
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?
additional information
?
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besides S-benzyl-L-cysteine and leukotriene E4, enzyme is inactive on physiological amines or amino acids L-aspartate, L-lysine, L-cystine, L-methionine, L-ethionine, L-cystathionine, or L-phenylalanine, L-tyrosine, and L-tryptophan
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?
additional information
?
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no substrate: aniline, o-aminobenzoate, D-cysteine, L-methionine, L-leucine, L-phenylalanine, L-glutamate
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?
additional information
?
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comparison of haloalkene-derived cysteine S-conjugates
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?
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acetyl-CoA + an S-substituted L-cysteine
CoA + an S-substituted N-acetyl-L-cysteine
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final reaction of mercapturic biosynthesis
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?
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5,5'-dithiobis-2-nitrobenzoic acid
strong inhibition
octyl glucoside
10 mM, 80% residual activity. Slight activation at 1 mM
p-chloromercuribenzoate
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probenecid
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less pronounced inhibition
additional information
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not inhibitory: PMSF
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octyl glucoside
1 mM, slight stimulation, inhibitory at higher concentration
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0.023
acetyl-CoA
pH 7.5, 37°C
2.6
O-benzyl-L-serine
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0.19 - 0.39
S-(1,2,3,4,4-pentachloro-butadienyl)-L-cysteine
0.0267
S-1-menaphthyl-L-cysteine
pH 7.5, 37°C
0.0291 - 0.176
S-4-nitrobenzyl-L-cysteine
0.0285 - 0.14
S-Benzyl-L-cysteine
0.063
S-butyl-L-cysteine
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7.1
S-ethyl-L-cysteine
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0.67
S-propyl-L-cysteine
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additional information
additional information
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0.19
S-(1,2,3,4,4-pentachloro-butadienyl)-L-cysteine
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0.39
S-(1,2,3,4,4-pentachloro-butadienyl)-L-cysteine
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0.0291
S-4-nitrobenzyl-L-cysteine
pH 7.5, 37°C
0.176
S-4-nitrobenzyl-L-cysteine
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0.0285
S-Benzyl-L-cysteine
pH 7.5, 37°C
0.064
S-Benzyl-L-cysteine
pH 7.5, 37°C
0.14
S-Benzyl-L-cysteine
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additional information
additional information
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substitution of oxygen for sulfur as in O-benzyl-L-serine, greatly increases the apparent Km, with only slight decrease in maximal velocity
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additional information
additional information
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radioactive assay
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additional information
additional information
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nonradioactive assay and separation by HPLC, kinetics
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UniProt
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NAT8_HUMAN
227
1
25619
Swiss-Prot
Mitochondrion (Reliability: 5 )
NAT8_MOUSE
227
1
25638
Swiss-Prot
Mitochondrion (Reliability: 5 )
NAT8_RAT
222
2
24894
Swiss-Prot
Secretory Pathway (Reliability: 5 )
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29000
x * 29000, SDS-PAGE of recombinant protein including His-tag
34000
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1 * 34000, SDS-PAGE
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?
x * 29000, SDS-PAGE of recombinant protein including His-tag
monomer
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1 * 34000, SDS-PAGE
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E104K
frequently found single nucleotide polymorphism, does not change enzymic activity or the expression of protein by more than 2fold
F143S
frequently found single nucleotide polymorphism, does not change enzymic activity or the expression of protein by more than 2fold
R149K
suppression of activity
additional information
a truncated protein starting from residue M25 shows no cysteinyl-S-conjugate N-acetyltransferase activity
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-20 C, stable for several months
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4°C, glycine/deoxyBIGCHAP buffer, pH 7.0, considerable inactivation
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expression in HEK-293T cell
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medicine
the frequently found single nucleotide polymorphisms, E104K or F143S, do not change enzymic activity or the expression of protein by more than 2fold
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Duffel, M.W.; Jakoby, W.B.
Cysteine S-conjugate N-acetyltransferase
Methods Enzymol.
113
516-521
1985
Rattus norvegicus
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Aigner, A.; Jaeger, M.; Pasternack, R.; Weber, P.; Wienke, D.; Wolf, S.
Purification and characterization of cysteine-S-conjugate N-acetyltransferase from pig kidney
Biochem. J.
317
213-218
1996
Sus scrofa
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Kraus, T.; Uttamsingh, V.; Anders, M.W.; Wolf, S.
Porcine kidney microsomal cysteine S-conjugate N-acetyltransferase-catalyzed N-acetylation of haloalkene-derived cysteine S-conjugates
Drug Metab. Dispos.
28
440-445
2000
Sus scrofa
brenda
Aigner, A.; Jaeger, M.; Weber, P.; Wolf, S.
A nonradioactive assay for microsomal cysteine-S-conjugate N-acetyltransferase activity by high-pressure liquid chromatography
Anal. Biochem.
223
227-231
1994
Sus scrofa
brenda
Green, T.; Lee, R.; Farrar, D.; Hill, J.
Assessing the health risks following environmental exposure to hexachlorobutadiene
Toxicol. Lett.
138
63-73
2003
Homo sapiens, Rattus norvegicus
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Veiga-da-Cunha, M.; Tyteca, D.; Stroobant, V.; Courtoy, P.J.; Opperdoes, F.R.; Van Schaftingen, E.
Molecular identification of NAT8 as the enzyme that acetylates cysteine S-conjugates to mercapturic acids
J. Biol. Chem.
285
18888-18898
2010
Homo sapiens (Q9UHE5)
brenda
Deol, R.; Josephy, P.
Acetylation of aromatic cysteine conjugates by recombinant human N-acetyltransferase 8
Xenobiotica
47
202-207
2017
Homo sapiens (Q9UHE5)
brenda
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