Abstract
Mycobacteria synthesize considerable quantities of a wide variety of fatty acids. In the mycolic acid series, for example, fatty acids containing over 80 carbon atoms have been detected. They represent the major lipid components of the cell walls of these organisms, and many studies have been devoted to their characterization. The shorter chain fatty acids (below C40) have also been studied extensively, especially the branched chain series.1 In fact mycobacteria produce highly complex mixtures of fatty acids. In Mycobacterium phlei, for example, more than 40 different fatty acids from C12 to C36 have been detected by gas chromatography-mass spectrometry (GC-MS).2
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
J. Asselineau, Branched-fatty acids of mycobacteria, Ind. J. Chest Dis. 24: 143 (1982).
I. M. Campbell and J. Naworal, Composition of the saturated and monounsaturated fatty acids of Mycobacterium phlei, J. Lipid Res. 10: 593 (1969).
A. J. V. Ferrer-Correira, K. R. Jennings, and D. K. Sen-Sharma, The use of ion-molecule reactions in the mass spectrometric location of double bonds, Org. Mass Spectrom. 11: 867 (1976).
R. Chai and A. G. Harrison, Location of double bonds by chemical ionization mass spectrometry, Anal. Chem. 53: 34 (1981).
A. Brauner, H. Budzikiewicz, and W. Francke, Chemical ionization (NO) spectra of n-alkenoic acids and their esters, Org. Mass Spectrom. 20: 578 (1985).
D. A. Peake and M. L. Gross, Iron (I) chemical ionization and tandem mass spectrometry for locating double bonds, Anal. Chem. 57: 115 (1985).
D. A. Peake, S. K. Huang, and M. L. Gross, Iron (I) chemical ionization for analysis of alkene and alkyne mixtures by tandem sector mass spectrometry or gas chromatography/Fourier transform mass spectrometry, Anal. Chem. 59: 1557 (1987).
B. A. Andersson and R. T. Holman, Pyrolidides for mass spectrometric determination of the position of the double bond in monounsaturated fatty acids, Lipids 9: 185 (1974).
D. J. Harvey, Picolinyl esters as derivatives for the structural determination of long chain branched and unsaturated fatty acids, Biomed. Mass Spectrom. 9: 33 (1982).
W. W. Christie, E. Y. Brechany, and R. T. Holman, Mass spectra of the picolinyl esters of isomeric mono and dienoic fatty acids, Lipids 22: 224 (1987).
N. J. Jensen, K. B. Tomer, and M. L. Gross, Gas-Phase ion decompositions occurring remote to a charge site, J. Am. Chem. Soc. 107: 1863 (1985).
K. B. Tomer, F. W. Crow, and M. L. Gross, Location of double bond position in unsaturated fatty acids by negative ion MS/MS, J. Am. Chem. Soc. 105: 5487 (1983).
N. J. Jensen and M. L. Gross, Fast atom bombardment and tandem mass spectrometry for determining iso-and anteiso-fatty acids, Lipids 21: 362 (1986).
J. Adams and M. L. Gross, Tandem mass spectrometry for collisional activation of alkali-metal-cationized fatty acids: a method for determining double bond location, Anal. Chem. 59: 1576 (1987).
M. Bambagiotti, S. A. Coran, V. Gianellini, F. F. Vincieri, S. Daolio, and P. Traldi, Structural identification of fatty acid methyl esters by collision spectra of their [M-H]-species, Org. Mass Spectrom. 19: 577 (1984).
O. Takeuchi, M. Weiss, and A. G. Harrison, Location of double bonds in alkenyl acetates by negative ion tandem mass spectrometry, Anal. Chem. 59: 918 (1987).
J. C. Prome, H. Aurelle, F. Couderc, and A. Savagnac, Structural determination of unsaturated fatty acids in complex mixtures by capillary GC/MS-MS, Rapid Comm., Mass Spectrom. 1: 50 (1987).
C. P. Asselineau, C. S. Lacave, H. L. Montrozier, and J. C. Prome, Relations structurales entre les acides mycoliques insatures et les acides inferieurs insatures synthetises par Mycobacterium phlei. Implications metaboliques, Eur. J. Biochem. 14: 406 (1970).
J. G. C. Hung and R. W. Walker, Unsaturated fatty acids of Mycobacteria, Lipids 5: 720 (1970).
K. Takayama, N. Qureshi, and H. K. Schnoes, Isolation and characterization of the monounsaturated long chain fatty acids of Mycobacterlum tuberculosis, Lipids 13: 575 (1978).
M. Cervilla and G. Puzo, Determination of double bond position in monounsaturated fatty acids by mass analyzed ion kinetic energy spectrometry-collision-induced dissociation after chemical ionization of their amino alcohol derivatives, Anal. Chem. 55: 2100 (1983).
C. P. Asselineau, H. L. Montrozier, and J. C. Prome, Presence d’acides polyinsatures dans une bacterie: isolement, a partir des lipides de Mycobacterlum phlei, d’acide hexatriacontapentaene-4,8,16,20-oique et d’acides analogues, Eur. J. Biochem. 10: 580 (1969).
C. P. Asselineau, H. L. Montrozier, J. C. Prome, A. M. Savagnac, and M. Welby, Etude d’un glycolipide polyunsature synthetise par Mycobacterium phlei, Eur. J. Biochem. 28: 102 (1972).
C. P. Asselineau and H. L. Montrozier, Etude du processus de biosynthese des acides phleiques, acides polyunsatures synthetises par Mycobacterium phlei, Eur. J. Biochem. 63: 509 (1976).
N. J. Jensen, K. B. Tomer, and M. L. Gross, Collisional activation decomposition mass spectra for locating double bonds in polyunsaturated fatty acids, Anal. Chem. 57: 2018 (1985).
H. Aurelle, M. Treilhou, D. Prome, A. Savagnac, and J. C. Prome, Analysis of mycobacterial polyunsaturated fatty acids (“Phleic acids”) by remote site fragmentation, Rapid Comm., Mass Spectrom. 1: 65 (1987).
F. Coudrec, H. Aurelly, D. Prome, A. Savagnac, and J. C. Prome, Analysis of fatty acids by negative ion gas chromatography/tandem mass spectrometry: structural correlations between α-mycolic acid chains and Δ5-monounsaturated fatty acids from Mycobacterium phlei, Biomed. Environ. Mass Spectrom. 16: 317 (1988).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1990 Springer Science+Business Media New York
About this chapter
Cite this chapter
Prome, JC., Aurelle, H., Couderc, F., Prome, D., Savagnac, A., Treilhou, M. (1990). Structural Determination of Unsaturated Long Chain Fatty Acids from Mycobacteria by Capillary Gas Chromatography and Collision Activation Dissociation Mass Spectrometry. In: Fox, A., Morgan, S.L., Larsson, L., Odham, G. (eds) Analytical Microbiology Methods. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-3564-9_11
Download citation
DOI: https://doi.org/10.1007/978-1-4899-3564-9_11
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4899-3566-3
Online ISBN: 978-1-4899-3564-9
eBook Packages: Springer Book Archive