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EC Tree
IUBMB Comments Requires Zn2+. The enzyme, characterized from the bacterium Corynebacterium sp. Ax20, hydrolyses odorless Nalpha-acyl-L-glutamine conjugates of short- and medium-chain fatty acids, releasing axillary malodor compounds. While the enzyme is highly specific for the L-glutamine moiety, it is quite promiscuous regarding the acyl moiety. The two most common products of the enzyme's activity in axillary secretions are (2E)-3-methylhex-2-enoate and 3-hydroxy-3-methylhexanoate.
The enzyme appears in viruses and cellular organisms
Reaction Schemes
an Nalpha-acyl-L-glutamine
+
=
+
Synonyms
acylglutamine-aminoacylase,
AgaA , AMRE, axillary malodor releasing enzyme, N(alpha)-acyl-glutamine aminoacylase, N-acyl-Gln aminoacylase, N-AGA,
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acylglutamine-aminoacylase
axillary malodor releasing enzyme
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N(alpha)-acyl-glutamine aminoacylase
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acylglutamine-aminoacylase
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acylglutamine-aminoacylase
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AgaA
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N-acyl-Gln aminoacylase
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N-acyl-Gln aminoacylase
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an Nalpha-acyl-L-glutamine + H2O = L-glutamine + a carboxylate
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Nalpha-acyl-L-glutamine amidohydrolase (carboxylate-forming)
Requires Zn2+. The enzyme, characterized from the bacterium Corynebacterium sp. Ax20, hydrolyses odorless Nalpha-acyl-L-glutamine conjugates of short- and medium-chain fatty acids, releasing axillary malodor compounds. While the enzyme is highly specific for the L-glutamine moiety, it is quite promiscuous regarding the acyl moiety. The two most common products of the enzyme's activity in axillary secretions are (2E)-3-methylhex-2-enoate and 3-hydroxy-3-methylhexanoate.
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(E)-3-methyl-2-hexenoyl-L-glutamine + H2O
L-glutamine + (E)-3-methyl-2-hexenoic acid
3-methyl-2-hexenoyl-L-glutamine + H2O
L-glutamine + 3-methyl-2-hexenoic acid
3-methyl-3-hydroxyhexanoyl-L-glutamine + H2O
L-glutamine + 3-methyl-3-hydroxyhexanoic acid
an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
benzyloxycarbonyl-L-glutamine + H2O
L-glutamine + benzyloxycarbonate
Nalpha-decanoyl-L-glutamine + H2O
L-glutamine + decanoic acid
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highest activity
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?
Nalpha-lauroyl-L-glutamine + H2O
L-glutamine + lauric acid
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?
additional information
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(E)-3-methyl-2-hexenoyl-L-glutamine + H2O
L-glutamine + (E)-3-methyl-2-hexenoic acid
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(E)-3-methyl-2-hexenoyl-L-glutamine + H2O
L-glutamine + (E)-3-methyl-2-hexenoic acid
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3-methyl-2-hexenoyl-L-glutamine + H2O
L-glutamine + 3-methyl-2-hexenoic acid
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3-methyl-2-hexenoyl-L-glutamine + H2O
L-glutamine + 3-methyl-2-hexenoic acid
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?
3-methyl-2-hexenoyl-L-glutamine + H2O
L-glutamine + 3-methyl-2-hexenoic acid
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?
3-methyl-3-hydroxyhexanoyl-L-glutamine + H2O
L-glutamine + 3-methyl-3-hydroxyhexanoic acid
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?
3-methyl-3-hydroxyhexanoyl-L-glutamine + H2O
L-glutamine + 3-methyl-3-hydroxyhexanoic acid
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3-methyl-3-hydroxyhexanoyl-L-glutamine + H2O
L-glutamine + 3-methyl-3-hydroxyhexanoic acid
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?
an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
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an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
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an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
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the enzyme is highly specific for the glutamine residue but has a low specificity for the acyl part of the substrate
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an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
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an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
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the enzyme is highly specific for the glutamine residue but has a low specificity for the acyl part of the substrate
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benzyloxycarbonyl-L-glutamine + H2O
L-glutamine + benzyloxycarbonate
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lowest activity
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benzyloxycarbonyl-L-glutamine + H2O
L-glutamine + benzyloxycarbonate
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lowest activity
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additional information
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the enzyme shows very weak activity for Z-Ala. No activity for Z-L-asparagine, Z-L-aspartate, N-lauroyl-L-aspartate, Z-L-glutamate nor is there any cleavage of Z-D-glutamine, the methyl ester of Z-L-glutamine or Z-Gln-Gly
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additional information
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the enzyme shows very weak activity for Z-Ala. No activity for Z-L-asparagine, Z-L-aspartate, N-lauroyl-L-aspartate, Z-L-glutamate nor is there any cleavage of Z-D-glutamine, the methyl ester of Z-L-glutamine or Z-Gln-Gly
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an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
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an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
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an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
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the enzyme is highly specific for the glutamine residue but has a low specificity for the acyl part of the substrate
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?
an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
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?
an Nalpha-acyl-L-glutamine + H2O
L-glutamine + a carboxylate
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the enzyme is highly specific for the glutamine residue but has a low specificity for the acyl part of the substrate
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?
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Mn2+
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partial loss of activity is observed with the combination Mn2+
additional information
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not inhibited by phenylmethylsulfonyl fluoride and Pefablock (4-(2-aminoethyl)-benzenesulfonyl fluoride) or with pepstatin
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0.2
(E)-3-methyl-2-hexenoyl-L-glutamine
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at pH 7.0 and 36°C
0.74
3-methyl-3-hydroxyhexanoyl-L-glutamine
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at pH 7.0 and 36°C
0.05
benzyloxycarbonyl-L-glutamine
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at pH 7.0 and 36°C
0.08
Nalpha-decanoyl-L-glutamine
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at pH 7.0 and 36°C
0.06
Nalpha-lauroyl-L-glutamine
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at pH 7.0 and 36°C
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brenda
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brenda
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physiological function
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the enzyme releases axillary malodor
physiological function
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the enzyme releases axillary malodor
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AGAA_CORST
400
0
43494
Swiss-Prot
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x * 48000, SDS-PAGE
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x * 43365, nano-ESI-MS analysis
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x * 48000, SDS-PAGE
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x * 43365, nano-ESI-MS analysis
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ammonium sulfate precipitation, DEAE-Sepharose CL-6B column chromatography, phenyl Sepharose column chromatography, and Mono Q column chromatography
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expressed in Escherichia coli BL21(DE3) cells
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expressed in Escherichia coli Top10 cells
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Natsch, A.; Derrer, S.; Flachsmann, F.; Schmid, J.
A broad diversity of volatile carboxylic acids, released by a bacterial aminoacylase from axilla secretions, as candicate molecules for the determination of human-body odor type
Chem. Biodivers.
3
1-20
2006
Corynebacterium sp.
brenda
Natsch, A.; Gfeller, H.; Gygax, P.; Schmid, J.
Isolation of a bacterial enzyme releasing axillary malodor and its use as a screening target for novel deodorant formulations
Int. J. Cosmet. Sci.
27
115-122
2005
Corynebacterium striatum, Corynebacterium striatum AX20
brenda
Natsch, A.; Gfeller, H.; Gygax, P.; Schmid, J.; Acuna, G.
A specific bacterial aminoacylase cleaves odorant precursors secreted in the human axilla
J. Biol. Chem.
278
5718-5727
2003
Corynebacterium striatum, Corynebacterium striatum AX20
brenda
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3.5.1.133 Nalpha-acyl-L-glutamine aminoacylase
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