OnLine ozonolysis methods for the determination of double bond position in unsaturated lipids

Methods in Molecular Biology

Volumn 579, Issue , 2009, Pages 413-441

  Thomas, Michael C ^a   Mitchell, Todd W ^a   Blanksby, Stephen J ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

Double bond position; Mass spectrometry; OzESI MS; OzID; Ozonolysis; Structural characterization; Unsaturated lipids

Indexed keywords

MONOUNSATURATED FATTY ACID; OZONE; UNSATURATED FATTY ACID; LIPID;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; COMPARATIVE STUDY; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; FLOW RATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; ION CURRENT; IONIZATION; LIPID ANALYSIS; MASS SPECTROMETRY; NONHUMAN; OXYGEN TENSION; OZONOLYSIS; PRIORITY JOURNAL; SIGNAL NOISE RATIO; STEREOCHEMISTRY; CHEMISTRY; GAS CHROMATOGRAPHY; METHODOLOGY;

CHROMATOGRAPHY, GAS; LIPIDS; OZONE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 74949103391     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-60761-322-0_21     Document Type: Article

References (25)

1. Han X, Gross RW. (2005) Shotgun lipidomics: multidimensional MS analysis of cellular lipidomes. Expert Rev Proteomic. 2(2):253–64.
2. Pulfer M, Murphy RC. (2003) Electrospray mass spectrometry of phospholipids. Mass Spectrom Rev. 22(5):332–64.
3. Moe MK, Anderssen T, Strom MB, Jensen E. (2004) Vicinal hydroxylation of unsaturated fatty acids for structural characterization of intact neutral phospholipids by negative electrospray ionization tandem quadrupole mass spectrometry. Rapid Comm Mass Spectrom. 18(18):2121–30.
4. Cook HW. (1996) Fatty acid desaturation and chain elongation in eukaryotes. In: Vance DE, Vance J, eds. Biochemistry of lipids, lipoproteins and membranes. Amsterdam: Elsevier: 129–52.
5. Fatty Acids and Eicosanoids. (Accessed at http://www.lipidlibrary.co.uk/Lipids/fa_eic.html.)
6. Pariza MW, Park Y, Cook ME. (2001) The biologically active isomers of conjugated linoleic acid. Prog Lipid Res. 40(4):283–98.
7. Ackman RG. (2002) The gas chromatograpy in practical analyses of common and uncommon fatty acids for the 21st century. Anal Chim Acta. 465:175–92.
8. Bryant DK, Orlando RC, Fenselau C, Sowder RC, Henderson LE. (1991) 4-Sector tandem mass-spectrometric analysis of complex-mixtures of phosphatidylcholines present in a human- Immunodeficiency-virus preparation. Anal Chem. 63(11):1110–4.
9. Moe MK, Anderssen T, Strom MB, Jensen E. (2005) Total structure characterization of unsaturated acidic phospholipids provided by vicinal di-hydroxylation of fatty acid double bonds and negative electrospray ionization mass spectrometry. J Am Soc Mass Spectrom. 16(1):46–59.
10. Moe MK, Strom MB, Jensen E, Claeys M. (2004) Negative electrospray ionization lowenergy tandem mass spectrometry of hydroxylated fatty acids: a mechanistic study. Rapid Commun Mass Spectrom. 18(15):1731–40.
11. Harrison KA, Murphy RC. (1996) Direct mass spectrometric analysis of ozonides: Application to unsaturated glycerophosphocholine lipids. Anal Chem. 68(18):3224–30.
12. Van Pelt CK, Carpenter BK, Brenna JT. (1999) Studies of structure and mechanism in acetonitrile chemical ionization tandem mass spectrometry of polyunsaturated fatty acid methyl esters. J Am Soc Mass Spectrom. 10(12):1253–62.
13. Van Pelt CK, Brenna JT. (1999) Acetonitrile chemical ionization tandem mass spectrometry to locate double bonds in polyunsaturated fatty acid methyl esters. Anal Chem. 71(10):1981–9.
14. Xu Y, Brenna JT. (2007) Atmospheric pressure covalent adduct chemical ionization tandem mass spectrometry for double bond localization in monoene- and diene-containing triacylglycerols. Anal Chem. 79(6):2525–36.
15. Thomas MC, Mitchell TW, Blanksby SJ. (2006) Ozonolysis of phospholipid double bonds during electrospray ionization: a new tool for structure determination. J Am Chem Soc. 128(1):58–9.
16. Thomas MC, Mitchell TW, Harman DG, Deeley JM, Murphy RC, Blanksby SJ. (2007) Elucidation of double bond position in unsaturated lipids by ozone electrospray ionization mass spectrometry. Anal Chem. 79(13):5013–22.
17. Grimm RL, Hodyss R, Beauchamp JL. (2006) Probing interfacial chemistry of single droplets with field-induced droplet ionization mass spectrometry: Physical adsorption of polycyclic aromatic hydrocarbons and ozonolysis of oleic acid and related compounds. Anal Chem. 75:3800–6.
18. Thomas MC, Mitchell TW, Harman DG, Deeley JM, Nealon JR, Blanksby SJ. (2008) Ozone-induced dissociation: elucidation of double bond position within mass-selected lipid ions. Anal Chem. 80(1):303–11.
19. Ozone compatible materials – Ozone solutions website (Accessed at http://www.ozoneapplications.com/info/ozone_compatible_materials.htm)
20. Ozone compatible materials – Ozone services website. (Accessed at http://www.ozoneservices.com/articles/003.htm.)
21. Harman DG, Blanksby SJ. (2007) Investigation of the gas phase reactivity of the 1-adamantyl radical using a distonic radical anion approach. Org Biomol Chem. 5:3495–503.
22. Limits for air contaminants – Occupational Safety and Health Administration. (Accessed at http://www.osha.gov/pls/oshaweb/owadisp.show_document?p_table=STANDARDS&p_id=9992.)
23. IDLH documentation – Centres for Disease Control and Prevention. (Accessed at http://www.cdc.gov/Niosh/idlh/10028156.html.)s
24. MSDS for ozone. (Accessed at http://www.ozoneapplications.com/info/ozone_msds.htm.)
25. Baba S, Satoh S, Yamabe C. (2002) Development of measurement equipment of half life of ozone. Vacuum. 65:489–95.