Parent Class:

EC-Numbers → 3 -- Hydrolases → 3.5 -- Acting on carbon-nitrogen bonds, other than peptide bonds → 3.5.1 -- In linear amides

Synonyms: AMRE, axillary malodor releasing enzyme, agaA (gene name)

Systematic Name: N^α-acyl-L-glutamine amidohydrolase (carboxylate-forming)

Unification Links: BRENDA:3.5.1.133, ENZYME:3.5.1.133, IUBMB-ExplorEnz:3.5.1.133

Reaction:
an N^α-acyl-L-glutamine + H₂O → a carboxylate + L-glutamine

Unofficial Reactions:
N-carbobenzyloxy-L-glutamine + H₂O + H⁺ → benzyl alcohol + L-glutamine + CO₂,
N^α-(3-hydroxy-3-methylhexanoyl)-L-glutamine + H₂O → 3-hydroxy-3-methylhexanoate + L-glutamine,
N^α-[(2E)-3-methylhex-2-enoyl]-L-glutamine + H₂O → (2E)-3-methylhex-2-enoate + L-glutamine

Enzymes and Genes:
N^α-acyl-L-glutamine aminoacylase: agaA ( Corynebacterium sp. Ax20 )

Summary:
Requires Zn^s+. The enzyme, characterized from the bacterium Corynebacterium sp. Ax20, hydrolyzes odorless N^α-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.

Citations: [Natsch03, Natsch05, Natsch06]

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References

Natsch03: Natsch A, Gfeller H, Gygax P, Schmid J, Acuna G (2003). "A specific bacterial aminoacylase cleaves odorant precursors secreted in the human axilla." J Biol Chem 278(8);5718-27. PMID: 12468539

Natsch05: Natsch A, Gfeller H, Gygax P, Schmid J (2005). "Isolation of a bacterial enzyme releasing axillary malodor and its use as a screening target for novel deodorant formulations." Int J Cosmet Sci 27(2);115-22. PMID: 18492161

Natsch06: Natsch A, Derrer S, Flachsmann F, Schmid J (2006). "A broad diversity of volatile carboxylic acids, released by a bacterial aminoacylase from axilla secretions, as candidate molecules for the determination of human-body odor type." Chem Biodivers 3(1);1-20. PMID: 17193210

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 46(D1):D633-D639 2018
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