Volatile methyl esters of medium chain length from the bacterium Chitinophaga Fx7914.
The analysis of the volatiles released by the novel bacterial isolate Chitinophaga Fx7914 revealed the presence of ca. 200 compounds including different methyl esters. These esters comprise monomethyl- and dimethyl-branched, saturated, and unsaturated fatty acid methyl esters that have not been described as bacterial volatiles before. More than 30 esters of medium C-chain length were identified, which belong to five main classes, methyl (S)-2-methylalkanoates (class A), methyl (S)-2,(ω-1)-dimethylalkanoates (class B), methyl 2,(ω-2)-dimethylalkanoates (class C), methyl (E)-2-methylalk-2-enoates (class D), and methyl (E)-2,(ω-1)-dimethylalk-2-enoates (class E). The structures of the compounds were verified by GC/MS analysis and synthesis of the target compounds as methyl (S)-2-methyloctanoate (28), methyl (S)-2,7-dimethyloctanoate ((S)-43), methyl 2,6-dimethyloctanoate (49), methyl (E)-2-methylnon-2-enoate (20a), and methyl (E)-2,7-dimethyloct-2-enoate (41a). Furthermore, the natural saturated 2-methyl-branched methyl esters showed (S)-configuration as confirmed by GC/MS experiments using chiral phases. Additionally, the biosynthetic pathway leading to the methyl esters was investigated by feeding experiments with labeled precursors. The Me group at C(2) is introduced by propanoate incorporation, while the methyl ester is formed from the respective carboxylic acid by a methyltransferase using S-adenosylmethionine (SAM).
Nawrath
Thorben
T
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, Braunschweig.
Gerth
Klaus
K
Müller
Rolf
R
Schulz
Stefan
S
D003470:Culture Media; D004952:Esters; D005227:Fatty Acids / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification*; D005231:Fatty Acids, Unsaturated / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification*; D005232:Fatty Acids, Volatile / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification*; D008401:Gas Chromatography-Mass Spectrometry; D008745:Methylation; D015394:Molecular Structure; D045249:Sphingobacterium / Q000737:chemistry* / Q000254:growth & development / Q000378:metabolism; D013237:Stereoisomerism; D014835:Volatilization
D003470:Culture Media; D004952:Esters; D005227:Fatty Acids; D005231:Fatty Acids, Unsaturated; D005232:Fatty Acids, Volatile