Skip to main content
PMC home page
Biochemical Journal logoLink to Biochemical Journal
. 1970 Mar;117(1):119–128. doi: 10.1042/bj1170119

Biosynthesis of ubiquinone in non-photosynthetic Gram-negative bacteria

G R Whistance 1, B S Brown 1,*, D R Threlfall 1
PMCID: PMC1178837  PMID: 5420949

Abstract

1. The polyprenylphenol and quinone complements of the non-photosynthetic Gram-negative bacteria, Pseudomonas ovalis Chester, Proteus mirabilis and `Vibrio O1' (Moraxella sp.), were investigated. 2. Ps. ovalis Chester and Prot. mirabilis were shown to contain 2-polyprenylphenols, 6-methoxy-2-polyprenylphenols, 6-methoxy-2-polyprenyl-1,4-benzoquinones, 5-demethoxyubiquinones, ubiquinones, an unidentified 1,4-benzoquinone [2-polyprenyl-1,4-benzoquinone (?)] and `epoxyubiquinones'. `Vibrio O1' was shown to contain only 5-demethoxyubiquinones, ubiquinones and `epoxyubiquinones'. 3. It was established that in Ps. ovalis Chester 2-polyprenylphenols, 6-methoxy-2-polyprenylphenols, 6-methoxy-2-polyprenyl-1,4-benzoquinones, 5-demethoxyubiquinones and 2-polyprenyl-1,4-benzoquinones (?) are precursors of ubiquinones. 4. Intracellular distribution studies showed that in Ps. ovalis Chester ubiquinone and its prenylated precursors are localized entirely on the protoplast membrane. 5. Investigations into the oxygen requirements for ubiquinone biosynthesis by Ps. ovalis Chester showed that the organism could not convert p-hydroxybenzoic acid into ubiquinone in the absence of oxygen, although it could convert a limited amount into 2-polyprenylphenols. 6. Attempts were made to prepare cell-free preparations capable of synthesizing ubiquinone. Purified protoplast membranes of Ps. ovalis Chester were found to be incapable of carrying out this synthesis, even when supplemented with cytoplasm. With crushed-cell preparations of Ps. ovalis Chester, organism PC4 (Achromobacter sp.) and Escherichia coli, synthesis was observed, although this was attributable in part to a small number of intact cells present in the preparations.

Full text

PDF
119

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. BISHOP D. H., KING H. K. Ubiquinone and vitamin K in bacteria. 2. Intracellular distribution in Escherichia coli and Micrococcus lysodeikticus. Biochem J. 1962 Dec;85:550–554. doi: 10.1042/bj0850550. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Daves G. D., Jr, Friis P., Olsen R. K., Folkers K. The chemistry of ubiquinone. Vitam Horm. 1966;24:427–439. doi: 10.1016/s0083-6729(08)60214-9. [DOI] [PubMed] [Google Scholar]
  3. Daves G. D., Jr, Wilczynski J. J., Friis P., Folkers K. Synthesis of rhodoquinone and other multiprenyl-1,4-benzoquinones biosynthetically related to ubiquinone. J Am Chem Soc. 1968 Sep 25;90(20):5587–5593. doi: 10.1021/ja01022a050. [DOI] [PubMed] [Google Scholar]
  4. Friis P., Daves G. D., Jr, Folkers K. New epoxyubiquinones. Biochemistry. 1967 Nov;6(11):3618–3624. doi: 10.1021/bi00863a037. [DOI] [PubMed] [Google Scholar]
  5. Friis P., Nilsson J. L., Daves G. D., Jr, Folkers K. New multiprenylquinones in the biosynthesis of ubiquinone. Biochem Biophys Res Commun. 1967 Aug 7;28(3):324–327. doi: 10.1016/0006-291x(67)90312-9. [DOI] [PubMed] [Google Scholar]
  6. LAWSON D. E., THRELFALL D. R., GLOVER J., MORTON R. A. Biosynthesis of ubiquinone in the rat. Biochem J. 1961 Apr;79:201–208. doi: 10.1042/bj0790201. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Nagata Y., Mizuno S., Maruo B. Preparation and properties of active membrane systems from various species of bacteria. J Biochem. 1966 Apr;59(4):404–410. doi: 10.1093/oxfordjournals.jbchem.a128316. [DOI] [PubMed] [Google Scholar]
  8. Olsen R. K., Daves G. D., Jr, Moore H. W., Folkers K., Parson W. W., Rudney H. 2-multiprenylphenols and 2-decaprenyl-6-methoxyphenol, biosynthetic precursors of ubiquinones. J Am Chem Soc. 1966 Dec 20;88(24):5919–5923. doi: 10.1021/ja00976a036. [DOI] [PubMed] [Google Scholar]
  9. PARSON W. W., RUDNEY H. AN INTERMEDIATE IN THE CONVERSION OF P-HYDROXYBENZOATE-U-C-14 TO UBIQUINONE IN RHODOSPIRILLUM RUBRUM. Proc Natl Acad Sci U S A. 1965 Mar;53:599–606. doi: 10.1073/pnas.53.3.599. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. PARSON W. W., RUDNEY H. THE BIOSYNTHESIS OF THE BENZOQUINONE RING OF UBIQUINONE FROM P-HYDROXYBENZALDEHYDE AND P-HYDROXYBENZOIC ACID IN RAT KIDNEY, AZOTOBACTER VINELANDII, AND BAKER'S YEAST. Proc Natl Acad Sci U S A. 1964 Mar;51:444–450. doi: 10.1073/pnas.51.3.444. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. REBEL G., SENSENBRENNER M., MANDEL P. RECHERCHES SUR LES LIPIDES DES FORMES L D'ERIV'EES DU PROTEUS P 18. 3. R'EPARTITION SUBCELLULAIRE DES QUINONES TRANSPORTEUSES D''ELECTRONS DANS LE BACILLE PROTEUS ET LES FORMES L QUI EN D'ERIVENT. Bull Soc Chim Biol (Paris) 1964;46:1113–1119. [PubMed] [Google Scholar]
  12. Spiller G. H., Threlfall D. R., Whistance G. R. Biosynthesis of ubiquinone in yeast, Phycomyces blakesleeanus, and Agaricus campestris. Arch Biochem Biophys. 1968 Jun;125(3):786–796. doi: 10.1016/0003-9861(68)90515-8. [DOI] [PubMed] [Google Scholar]
  13. Threlfall D. R., Goodwin T. W. Nature, intracellular distribution and formation of terpenoid quinones in Euglena gracilis. Biochem J. 1967 May;103(2):573–588. doi: 10.1042/bj1030573. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Threlfall D. R., Whistance G. R., Goodwin T. W. Biosynthesis of phytoquinones. Incorporation of L-[Me-14C,3H]methionine into terpenoid quinones and chromanols in maize shoots. Biochem J. 1968 Jan;106(1):107–112. doi: 10.1042/bj1060107. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Whistance G. R., Brown B. S., Threlfall D. R. Isolation of possible ubiquinone precursors from nonphotosynthetic Gram-negative bacteria. Biochim Biophys Acta. 1969 Jun 10;176(4):895–897. doi: 10.1016/0005-2760(69)90275-6. [DOI] [PubMed] [Google Scholar]
  16. Whistance G. R., Dillon J. F., Threlfall D. R. The nature, intergeneric distribution and biosynthesis of isoprenoid quinones and phenols in gram-negative bacteria. Biochem J. 1969 Feb;111(4):461–472. doi: 10.1042/bj1110461. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Whistance G. R., Threlfall D. R., Goodwin T. W. Observations on the biosynthesis of phytoterpenoid quinone and chromanol nuclei. Biochem J. 1967 Oct;105(1):145–154. doi: 10.1042/bj1050145. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES