Warianty tytułu
Języki publikacji
Abstrakty
Three different mass spectrometric method suitable for the analysis of polyprenyl and dolichyl phosphates and their glycosylated forms are described. Fast atom bombardment mass spectrometry (FAB MS) of glycosyl monophosphopolyprcnols produces negative ions characteristic of the intact molecule. Tandem mass spectrometry of (M-H)~ anions allows the determination of masses of both glycosyl and lipid moieties. Thus, for example, FAB-MS/MS of a mixture of native glycosyl monophosphopolyprenols isolated from ethambutol-treated Mycobacterium smegmatis enabled us to detect two novel pentosyl monophosphopolyprenols. Two other methods are proposed for the analysis of prenyl phosphates, as these compounds do not produce fragments in FAB-MS/MS at low collisional energy. By Desorption Electron Impact ionization (DEI) an intense (M-H3PO4)* ion as well as fragments corresponding to the successive loss of isoprene residues (68 Da) can be observed. Alternatively, Desorption Chemical Ionization yields ions corresponding to the loss of 66, 78 and 98 Da (i.e. of a part or the entire phosphate moiety) of a prenyl phosphate molecule. Tandem mass spectrometry of the (M-H-98)" ion gives a series of intense fragments differing by 68 mass units over the whole mass range.
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Czasopismo
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Tom
Numer
Opis fizyczny
p.345-349,fig.
Twórcy
autor
- University of Louvain, Pl.L.Pasteur 1, B-1348 Louvain-la-Neuve, Belgium
autor
Bibliografia
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- 2. Baynes, J.W-, Hsu, A.-F. & Heath, E.C. (1973) The role of mannosyl-phosphoryl-dihydropoly- isoprenol in the synthesis of mammalian glycoproteins. /. Biol. Chem. 248, 5693-5704.
- 3. Jung, P. & Tanner, W. (1973) Identification of the lipid intermediate in yeast mannan biosynthesis. Eur. J. Biochem. 37,1-6.
- 4. Stone, K.J. & Strominger, J.L. (1972) Isolation of Css-isoprenylpyrophosphate from Micrococcus lysodeikticus. J. Biol. Chem. 247,5107-5112.
- 5. Ilermansson, K., Jansson, P.E., Low, P., Dallner, G., Swie/.ewska, E. & Chojnacki, T. (1992) Analysis of long-chain polyisoprenoids by fast atom bombardment mass spectrometry. Biol. Mass Spectrom. 21,548-553.
- 6. Kitaoka, M., Nagaki, H., Kinoshita, T., Kurabayashi, M., Koyama, T. & Ogura, K. (1990) Negative ion fast atom bombardment-tandem mass spectrometry for structural analysis of isoprenoid diphosphates. Anal. Biochem. 185, 182-186.
- 7. Takayama, K. & Goldman, D.S. (1970) Enzymatic synthesis of mannosyl-l-phos- phoryl-decaprenol by a cell-free system of Mycobacterium tuberculosis. J. Biol. Chem. 245, 6251-6257.
- 8. Takayama, K., Schnoes, U.K. & Semmler, E.G. (1974) Characterization of the alkali-stable mannophospholipids of Mycobacterium smegma- tis. Biochim. Biophys. Acta 316, 212-221.
- 9. Scher, M., Lennarz, W.J. & Sweeley, C.C. (1968) The biosynthesis of mannosyl-l-phosphoryl- -polyisoprenol in Micrococcus lysodeikticus and its role in mannan synthesis. Proc. Natl. Acad. Sci. U.S.A. 59,1313-1320.
- 10. Troy, F.A., Frerman, F.E. & Heath, E.C. (1971) The biosynthesis of capsular polysaccharides in Aerobacter aerogenes. J. Biol. Chem. 244, 4406-4412.
- 11. Anderson, R.G., Hussey, H. & Baddiley, J. (1972) The mechanism of wall synthesis in bacteria. The organization of enzymes and isoprenoid phosphates in the membrane. Biochem. J. 127, 11-25.
- 12. Lechner, J., Wieland, F. & Sumper, M. (1985) Biosynthesis of sulfated saccharides N-glycosidically linked to the protein via glucose. Purification and identification of sulfated dolichyl monophosphoryl tetra- saccharides from halobacteria. J. Biol. Chem. 260,860-866.
- 13. Wolucka, B.A. (1992) Studies on D-arabinose metabolism in mycobacteria. Isolation of two novel glycolipids from Mycobacterium smegma tis. Ph.D. Thesis, University of Lou vain, Louvain-la-Neuve.
- 14. Wolucka, B.A., McNeil, M.R., Brennan, P.J., Kalbe, L. & Cocito, C. (1993) Isolation and characterization of arabinosyl- and ribosyl- -1-monophosphopolyprenols in Mycobacterium smegmatis. Glycoconj. J. 10,231-232.
- 15. Wolucka, B.A., de Hoffmann, E., Chojnacki, T., Kalbe, L., Cocito, C., McNeil, M.R. & Brennan, P.J. (1993) Identification of the carrier lipid for arabinan biosynthesis in mycobacteria. Twenty-eight U.S.-Japan Tuberculosis Research Conference. National Institutes of Health, Bethesda, Maryland, pp. 202-207.
- 16. Wolucka, B.A., McNeil, M.R., de Hoffmann, E., Chojnacki, T. & Brennan, P.J. (1994) Recognition of the lipid intermediate for arabinogala- ctan/arabinomannan biosynthesis and its relation to the mode of action of ethambutol on mycobacteria. J. Biol. Chem. (submitted).
- 17. Takayama, K. & Kilburn, J.O. (1989) Inhibition of synthesis of arabinogalactan by ethambutol in Mycobacterium smegmatis. Antimicrob. Agents Chemother. 33,1493-1499.
- 18. Waeghe, T.J., Darvill, A.G., McNeil, M. & Albersheim, P. (1983) Determination, by methylation analysis of the glycosyl-linkage compositions of microgram quantities of complex carbohydrates. Carbohydr. Res. 123, 281-304.
- 19. Wellburn, A.R., Stevenson, J., Hemming, F.W. & Morten, R.A. (1967) The characterization and properties of castaprenol-11, -12 and -13 from leaves of Aesculus hippocastanum (horse chestnut). Biochem. J. 102, 313-324.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.agro-article-fdddf818-a68d-4f5e-ad3f-38ea6d4d787c