S-methyl thioesters are produced from fatty acids and branched-chain amino acids by brevibacteria: Focus on L-leucine catabolic pathway and identification of acyl-CoA intermediates

Applied Microbiology and Biotechnology

Volumn 93, Issue 4, 2012, Pages 1673-1683

  Sourabié, Alain M ^a,b   Spinnler, Henry Eric ^b   Bourdat Deschamps, Marjolaine ^c   Tallon, Richard ^a   Landaud, Sophie ^b   Bonnarme, Pascal ^b  

^a Bio Springer   (France)

^b AGROPARISTECH   (France)

^c UMR 1402 ECOSYS   (France)

Author keywords

Acyl CoA intermediates; Biosynthesis pathway; Branched chain amino acids; Brevibacteria; S methyl thioesters; Short chain fatty acids

Indexed keywords

ACYL-COA; BIOSYNTHESIS PATHWAY; BREVIBACTERIA; SHORT-CHAIN FATTY ACIDS; THIOESTERS;

BIOCHEMISTRY; BIOSYNTHESIS; EXPERIMENTS; GAS CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

AMINO ACIDS;

ACYL COENZYME A; BRANCHED CHAIN AMINO ACID; FATTY ACID; LEUCINE; S METHYL THIOESTER; S METHYL THIOISOBUTYRATE; S METHYL THIOISOVALERATE; THIOACETIC ACID S METHYL ESTER; THIOESTER; UNCLASSIFIED DRUG;

AMINO ACID; BACTERIUM; CATABOLISM; CHROMATOGRAPHY; ENZYME ACTIVITY; ESTER; FATTY ACID; MASS SPECTROMETRY;

ARTICLE; BIOSYNTHESIS; BREVIBACTERIACEAE; CATABOLISM; CONTROLLED STUDY; LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; NONHUMAN; TANDEM MASS SPECTROMETRY;

ACYL COENZYME A; AMINO ACIDS, BRANCHED-CHAIN; BREVIBACTERIUM; CHEESE; CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, LIQUID; FATTY ACIDS; LEUCINE; MASS SPECTROMETRY; METABOLIC NETWORKS AND PATHWAYS; SULFUR COMPOUNDS;

BREVIBACTERIUM ANTIQUUM; BREVIBACTERIUM AURANTIACUM;

EID: 84857911352     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-011-3500-3     Document Type: Article

References (30)

1. Amarita F, Yvon M, Nardi M, Chambellon E, Delettre J, Bonnarme P (2004) Identification and functional analysis of the gene encoding methionine-γ- lyase in Brevibacterium linens. Appl Environ Microbiol 70:7348-7354 (Pubitemid 39643800)
2. Arfi K, Landaud S, Bonnarme P (2006) Evidence for distinct L-methionine catabolic pathways in the yeast Geotrichum candidum and the bacterium Brevibacterium linens. Appl Environ Microbiol 72:2155-2162
3. Babbitt PC, Kenyon GL, Martin BM, Charest H, Sylvestre M, Scholten JD, Chang KH, Liang PH, Dunaway-Mariano D (1992) Ancestry of the 4-chlorobenzoate dehalogenase: analysis of amino acid sequence identities among families of acyl:adenyl ligases, enoyl-CoA hydratases/isomerases, and acyl-CoA thioesterases. Biochemistry 31:5594-5604
4. Berger C, Martin N, Collin S, Gijs L, Khan JA, Piraprez G, Spinnler HE, Vulfson EN (1999) Combinatorial approach to flavor analysis: II olfactory investigation of a library of S-methyl thioesters and sensory evaluation of selected components. J Agric Food Chem 47:3274-3279 (Pubitemid 29422027)
5. Bonnarme P, Psoni L, Spinnler HE (2000) Diversity of L-methionine catabolism in cheese-ripening bacteria. Appl Environ Microbiol 66:5514-5517 (Pubitemid 32217168)
6. Bosset JO, Gauch R (1993) Comparison of volatile flavour compounds of six European "AOC" cheeses by using a new dynamic headspace GC-MS method. Int Dairy J 3:359-377
7. Bradford MM (1976) A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254
8. Collin S, Osman M, Delcambre S, El-Zayat AI, Dufour JP (1993) Investigation of volatile flavor compounds in fresh and ripened Domiati cheeses. J Agric Food Chem 41:1659-1663
9. Dias B, Weimer B (1998) Purification and characterization of L-methionine- γ-lyase from Brevibacterium linens BL2. Appl Environ Microbiol 64:3327-3331 (Pubitemid 28411454)
10. Dickinson JR, Dawes IW (1992) The catabolism of branched-chain amino acids occurs via 2-oxoacid dehydrogenase in Saccharomyces cerevisiae. J Gen Microbiol 138:2029-2033
11. 13C nuclear magnetic resonance investigation of the metabolism of leucine to isoamyl alcohol in Saccharomyces cerevisiae. J Biol Chem 272:26871-26878
12. Ferchichi M, Hemme D, Nardi M, Pamboukdjian N (1985) Production of methanethiol from methionine by Brevibacterium linens CNRZ 918. J Gen Microbiol 131:715-723 (Pubitemid 15082270)
13. Forquin MP, Duvergey H, Proux C, Loux V, Mounier J, Landaud S, Coppée JY, Gibrat JF, Bonnarme P, Martin-Verstraete I, Vallaeys T (2009) Identification of Brevibacteriaceae by multilocus sequence typing and comparative genomic hybridization analyses. Appl Environ Microbiol 75:6406-6409
14. Ganesan B, Seefeld K, Weimer BC (2004) Fatty acid production from amino acids and ?-keto acids by Brevibacterium linens BL2. Appl Environ Microbiol 70:6385-6393 (Pubitemid 39518541)
15. Helinck S, Spinnler HE, Parayre S, Dame-Cahagne M, Bonnarme P (2000) Enzymatic versus spontaneous S-methyl thioester synthesis in Geotrichum candidum. FEMS Microbiol Let 193:237-241
16. Horswill AR, Escalante-Semerena JC (2002) Characterization of the propionyl-CoA synthetase (PrpE) enzyme of Salmonella enterica: residue Lys592 is required for propionyl-AMP synthesis. Biochemistry 41:2379-2387 (Pubitemid 34160900)
17. Lamberet G, Auberger B, Bergère JL (1997a) Aptitude of cheese bacteria for volatile S-methyl thioesters synthesis I. Effects of substrates and pH on their formation by Brevibacterium linens GC171. Appl Microbiol Biotechnol 47:279-283 (Pubitemid 27173444)
18. Lamberet G, Auberger B, Bergère JL (1997b) Aptitude of cheese bacteria for volatile S-methyl thioester synthesis II. Comparison of Coryneform bacteria, Micrococcaceae and lactic acid bacteria starters. Appl Microbiol Biotechnol 48:393-397 (Pubitemid 27430093)
19. Landaud S, Helinck S, Bonnarme P (2008) Formation of volatile sulfur compounds and metabolism of methionine and other sulfur compounds in fermented food. Appl Microbiol Biotechnol 77:1195-1205
20. Lowe PN, Hodgson JA, Perham RN (1983) Dual role of a single multienzyme complex in the oxidative decarboxylation of pyruvate and branched-chain 2-oxo acids in Bacillus subtilis. Biochem J 215:133-140
21. Maggio-Hall LA, Lyne P, Wolff JA, Keller NP (2008) A single acyl- CoA dehydrogenase is required for catabolism of isoleucine, valine and short-chain fatty acids in Aspergillus nidulans. Fungal Genet Biol 45:180-189 (Pubitemid 351192332)
22. Malcorps P, Dufour JP (1992) Short-chain and medium-chain aliphatic-ester synthesis in Saccharomyces cerevisiae. Eur J Biochem 210:1015-1022 (Pubitemid 23015804)
23. Martin N, Neelz V, Spinnler HE (2004) Suprathreshold intensity and odour quality of sulphides and thioesters. Food Qual Pref 15:247-257 (Pubitemid 38089218)
24. Perera MADN, Choi S-Y, Wurtele ES, Nikolau BJ (2009) Quantitative analysis of short-chain acyl-coenzymeAs in plant tissues by LCMS- MS electrospray ionization method. J Chromatogr B 877:482-488
25. Perham RN, Lowe PN (1988) Isolation and properties of the branched-chain 2-keto acid and pyruvate dehydrogenase multienzyme complex from Bacillus subtilis. Methods Enzymol 166:330-341
26. Sablé S, Cottenceau G (1999) Current knowledge of soft cheeses flavour and related compounds. J Agric Food Chem 47:4825-4836 (Pubitemid 30016904)
27. Vallet A, Lucas P, Lonvaud-Funel A, de Revel G (2008) Pathways that produce volatile sulphur compounds from methionine in Oenococcus oeni. J Appl Microbiol 104:1833-1840 (Pubitemid 351724989)
28. Verdier I, Coulon JB, Pradel P, Berdagué JL (1995) Effect of forage type and cow breed on the characteristics of matured Saint- Nectaire cheeses. Lait 175:523-533
29. Webb JL (1966) Arsenicals. Enzyme and metabolic inhibitors, vol. III. Academic Press, New York, NY, pp 595-793
30. Yvon M, Thirouin S, Rijnen L, Fromentier D, Gripon JC (1997) An aminotransferase from Lactococcus lactis initiates conversion of amino acids to cheese flavor compounds. Appl Environ Microbiol 63:414-419 (Pubitemid 27121320)