1887

Abstract

Menaquinone- (2-methyl-3-farnesyl-farnesyl-1,4-naphthoquinone) and a methyl-substituted menaquinone- (2,[5 or 8]-dimethyl-3-farnesyl-faniesyl-1,4-naphthoquinone) were the major isoprenoid quinones found in membrane preparations of and subsp. By reverse-phase high-performance liquid chromatography (HPLC) and thin-layer chromatography (TLC) the faster-eluting menaquinone- co-chromatographed with a menaquinone- standard. The identity of menaquinone- was confirmed by UV spectrophotometry, mass spectrometry and nuclear magnetic resonance (NMR) analysis. The slower-eluting methyl-substituted menaquinone- co-chromatographed with a menaquinone- standard by reverse-phase TLC but eluted between menaquinone- and menaquinone- standards by HPLC. The UV spectrum of the rnethyl-substituted menaquinone- did not correlate with either authentic menaquinone or demethylmenaquinone. Mass spectra showed an increase of 14 mass units when compared to menaquinone-, and indicated that a methyl substituent was on the naphthoquinone nucleus. NMR spectra confirmed the presence of a methyl substituent at a peri position (carbon-5 or -8) on the benzenoid ring.

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/content/journal/micro/10.1099/00221287-129-11-3385
1983-11-01
2024-04-25
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References

  1. Bentley R., Meganathan R. 1982; Biosynthesis of vitamin K (menaquinone) in bacteria. Microbiological Reviews 46:241–280
    [Google Scholar]
  2. Carlone G.M., Lascelles J. 1982; Aerobic and anaerobic respiratory systems inCampylobacter fetussubsp.jejuni grown in atmospheres containing hydrogen. Journal of Bacteriology 152:306–314
    [Google Scholar]
  3. Collins M.D., Jones D. 1981; Distribution of isoprenoid quinone structural types in bacteria and their taxonomic implications. Microbiological Reviews 45:316–354
    [Google Scholar]
  4. Collins M.D., Shah H.N., Minnikin D.E. 1980; A note on the separation of natural mixtures of bacterial menaquinones using reverse phase thin-layer chromatography. Journal of Applied Bacteriology 48:277–282
    [Google Scholar]
  5. Dulley J.R., Greene P.A. 1975; A simple technique for eliminating interference by detergents in the Lowry method of protein determination. Analytical Biochemistry 64:136–141
    [Google Scholar]
  6. Dunphy P.J., Brodie A.F. 1971; The structure and function of quinones in respiratory metabolism. Methods in Enzymology 18:407–461
    [Google Scholar]
  7. Harvey S., Lascelles J. 1980; Respiratory systems and cytochromes inCampylobacter fetussubsp.intestinalis. Journal of Bacteriology 144:917–922
    [Google Scholar]
  8. Hoffman P.S., Goodman T.G. 1982; Respiratory physiology and energy conservation efficiency of Campylobacter jejuni. Journal of Bacteriology 150:319–326
    [Google Scholar]
  9. Hollander R. 1981; The dependence on quinone specificity of terminal electron transport of bacteria. Current Microbiology 6:155–159
    [Google Scholar]
  10. Jackman L.M., Sternhell S. 1969; Long-range interproton coupling. In Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry 5312–344 Edited by Barton D.H.R., Doering W. New York: Pergamon Press;
    [Google Scholar]
  11. Kroger A. 1980; Bacterial electron transport to fumarate. In The Diversity of Bacterial Respiratory Systems 21–17 Edited by Knowles C.J. Boca Raton, Florida: CRC Press;
    [Google Scholar]
  12. Kroger A., Dad’Ak V. 1969; On the role of quinones in bacterial electron transport - the respiratory system ofBacillus megaterium. European Journal of Biochemistry 11:328–340
    [Google Scholar]
  13. Kroger A., Dad’Ak V., Klingenberg M., Diemer F. 1971; On the role of quinones in bacterial electron transport - differential roles of ubiquinones and menaquinones inProteus rettgeri. European Journal of Biochemistry 21:322–333
    [Google Scholar]
  14. Langemann A., Isler O. 1965; Chemistry of isoprenoid quinones. In Biochemistry of Quinones 189–147 Edited by Morton R.A. New York: Academic Press;
    [Google Scholar]
  15. Smibert R.M. 1981; The genusCampylobacter. In The Prokaryotes pp. 609–617 Edited by Starr M.P., Stolp H., Truper H.G., Balows A., Schlegel H.G. New York: Springer-Verlag;
    [Google Scholar]
  16. Streitwieser A.Jr Heathcock C.H. 1976; Phenols, phenyl ethers and quinones. In Introduction to Organic Chemistry pp. 998–1036 New York: Macmillan;
    [Google Scholar]
  17. Taber H. 1980; Functions of vitamin K2 in microorganisms. In Vitamin K Metabolism and Vitamin K-dependent Proteins pp. 177–187 Edited by Suttie J.W. Maryland: University Park Press;
    [Google Scholar]
  18. Taber H.W., Sugarman B.J., Halfenger G.M. 1981; Involvement of menaquinones in the active accumulation of aminoglycosides byBacillus subtilis. Journal of General Microbiology 123:143–149
    [Google Scholar]
  19. Thauer R.K., Jungermann K., Decker K. 1977; Energy conservation in chemotrophic anaerobic bacteria. Bacteriological Reviews 41:100–180
    [Google Scholar]
  20. Thomson R.H. 1971; Identification. In Naturally Occurring Quinones, 2nd edn.. pp. 39–92 New York: Academic Press;
    [Google Scholar]
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