Structure and absolute configuration of an unsaturated anteiso fatty acid from Bacillus megaterium

Journal of Chromatography. a
Simone HauffWalter Vetter

Abstract

Gas chromatography in combination with electron ionization mass spectrometry (GC/EI-MS) was used to determine the fatty acids of a membrane lipid from Bacillus megaterium. Special attention was put on the structure and absolute configuration of a monoenoic fatty acid previously described in this sample. GC/EI-MS operated in the selected ion monitoring mode was used to determine twelve fatty acids in the bacterium. Methyl esters were prepared to verify the presence of a 14-methylhexadecenoic acid (a17:1) isomer. The position of the double bond of the a17:1 isomer and four further monoenoic fatty acids was elucidated by means of their picolinyl esters produced by the transesterification of the phospholipid. For the a17:1 isomer, the double bond was located between C-5 and C-6. Silver ion liquid chromatography was used to verify that the double bond was in cis-configuration. The bacterial 14-methylhexadec-5-enoic acid (a17:1Delta5) is chiral due to the stereogenic C-14 carbon. Initial enantioselective measurements were carried out with isomers of a17:1Delta5 which were available in form of racemic and (S)-enantiopure cis- and trans-isomers of a17:1Delta12 previously synthesized. The cis-a17:1Delta12 enantiomers were partly resolve...Continue Reading

References

Nov 1, 1975·Lipids·R L GlassH Schlenk
Apr 16, 1971·Biochemical and Biophysical Research Communications·T Kaneda
Mar 1, 1957·The Biochemical Journal·M LIVINGSTONR P HANSEN
Apr 28, 2005·Journal of Agricultural and Food Chemistry·Paul WhittakerVirginia C Dunkel
Jul 21, 2005·Organic & Biomolecular Chemistry·Jeroen S DickschatStefan Schulz
May 19, 2007·Analytical Chemistry·Saskia ThurnhoferWalter Vetter

❮ Previous
Next ❯

Related Concepts

Related Feeds

Anthrax Vaccines (ASM)

Three different types of anthrax vaccines are available; a live-attenuated, an alum-precipitated cell-free filtrate and a protein recombinant vaccine. The effectiveness between the three is uncertain, but the live-attenuated have shown to reduce the risk of anthrax with low adverse events. Here is the latest research on anthrax vaccines.

Anthrax Vaccines

Three different types of anthrax vaccines are available; a live-attenuated, an alum-precipitated cell-free filtrate and a protein recombinant vaccine. The effectiveness between the three is uncertain, but the live-attenuated have shown to reduce the risk of anthrax with low adverse events. Here is the latest research on anthrax vaccines.

Anthrax

Anthrax toxin, comprising protective antigen, lethal factor, and oedema factor, is the major virulence factor of Bacillus anthracis, an agent that causes high mortality in humans and animals. Here is the latest research on Anthrax.