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Conversion of l -Leucine to Isovaleric Acid by Propionibacterium freudenreichii TL 34 and ITGP23
Abstract
Several branched-chain volatile compounds are involved in the flavor of Swiss cheese. These compounds are probably produced by enzymatic conversion of branched-chain amino acids, but the flora and the pathways involved remain hypothetical. Our aim was to determine the ability of Propionibacterium freudenreichii , which is one of the main components of the secondary flora of Swiss cheese, to produce flavor compounds during leucine catabolism. Cell extracts and resting cells of two strains were incubated in the presence of l -leucine, α-ketoglutaric acid, and cofactors, and the metabolites produced were determined by high-performance liquid chromatography and gas chromatography. The first step of leucine catabolism was a transamination that produced α-ketoisocaproic acid, which was enzymatically converted to isovaleric acid. Both reactions were faster at pH 8.0 than at acidic pHs. Cell extracts catalyzed only the transamination step under our experimental conditions. Small amounts of 3-methylbutanol were also produced by resting cells, but neither 3-methylbutanal norα-hydroxyisocaproic acid was detected. l -Isoleucine and l -valine were also converted to the corresponding acids and alcohols. Isovaleric acid was produced by both strains during growth in a complex medium, even under conditions simulating Swiss cheese conditions (2.1% NaCl, pH 5.4, 24°C). Our results show that P. frendenreichii could play a significant role in the formation of isovaleric acid during ripening.
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In P. freudenreichii, an α-ketoacid dehydrogenase complex is involved in the second step of leucine conversion.
“In P. freudenreichii, an α-ketoacid dehydrogenase complex is involved in the second step of leucine conversion since arsenicals, which are known inhibitors of α-ketoacid dehydrogenase complex [63], caused a drastic reduction in the conversion of α-ketoisocaproic acid to 3-methylbutyric acid [59].”
From Production of cheese flavour compounds derived from amino acid catabolism by Propionibacterium freudenreichii (2002) · cites this paper as [59]
Addition of α-KG to YEL cultures increases the amount of isovaleric acid by more than 80%.
“The addition of α-KG in YEL cultures induced an increase by more than 80% in the amount of isovaleric acid [59].”
From Production of cheese flavour compounds derived from amino acid catabolism by Propionibacterium freudenreichii (2002) · cites this paper as [59]
Replacing α-KG with pyruvic acid as amino group acceptor reduces Leu aminotransferase activity to about 4% of that observed with α-KG in two tested strains of P. freudenreichii.
“the replacement of α-KG with phenylpyruvic acid or pyruvic acid as amino group acceptor drastically reduced Leu aminotransferase activity, which was respectively only ~20% and 4% of that observed with α-KG in the two tested strains of P. freudenreichii [59].”
From Production of cheese flavour compounds derived from amino acid catabolism by Propionibacterium freudenreichii (2002) · cites this paper as [59]
Branched-chain amino acids are degraded by PAB cell-free extracts or resting cells only in the presence of an amino group acceptor such as α-ketoglutaric acid.
“these amino acids, either by cell-free extracts or resting cells, are degraded only in the presence of an acceptor of an amino group like α-ketoglutaric acid (α-KG) [59].”
From Production of cheese flavour compounds derived from amino acid catabolism by Propionibacterium freudenreichii (2002) · cites this paper as [59]
Replacing α-KG with phenylpyruvic acid as amino group acceptor reduces Leu aminotransferase activity to about 20% of that observed with α-KG in two tested strains of P. freudenreichii.
“the replacement of α-KG with phenylpyruvic acid or pyruvic acid as amino group acceptor drastically reduced Leu aminotransferase activity, which was respectively only ~20% and 4% of that observed with α-KG in the two tested strains of P. freudenreichii [59].”
From Production of cheese flavour compounds derived from amino acid catabolism by Propionibacterium freudenreichii (2002) · cites this paper as [59]
In P. freudenreichii, branched-chain α-keto acids derived from Val, Leu and Ile were mainly converted by resting cells of PAB to the corresponding acids, isobutyric acid, 3-methylbutyric acid and 2-methylbutyric acid, respectively.
“In P. freudenreichii, the branched-chain α-keto acids derived from Val, Leu and Ile, α-ketoisovaleric acid, α-ketoisocaproic acid, and α-keto-β-methylvaleric acid, respectively, were mainly converted by resting cells of PAB to the corresponding acids, isobutyric acid, 3-methylbutyric acid and 2-methylbutyric acid, respectively [59].”
From Production of cheese flavour compounds derived from amino acid catabolism by Propionibacterium freudenreichii (2002) · cites this paper as [59]
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Sorted by citations
Flavour formation by lactic acid bacteria and biochemical flavour profiling of cheese products
Smit, G., Smit, B. A., & Engels, W. J. M. (2005) · FEMS Microbiology Reviews · doi:10.1016/j.fmrre.2005.04.002 · Cited by 949
Thierry, A., & Maillard, M.-B. (2002) · Le Lait · doi:10.1051/lait:2001002 · Cited by 110
Self-citation
Metadata
- Authors
- Thierry, A., Maillard, M.-B., & Yvon, M.
- Affiliations
- Laboratoire de Recherches de Technologie Laitière, INRA, 35042 Rennes Cedex
- Unité de Recherches de Biochimie et Structure des Protéines, INRA, 78352 Jouy-en-Josas Cedex, France
- Venue
- Applied and Environmental Microbiology
- Publisher
- American Society for Microbiology
- Published
- 2002-02
- Volume
- 68
- Issue
- 2
- Pages
- 608-615
- ISSN
- 0099-2240
- 1098-5336
- Cited by
- 99
- References
- 3
- Language
- en
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