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. 1973 Apr;114(1):42–52. doi: 10.1128/jb.114.1.42-52.1973

Pathway for Ubiquinone Biosynthesis in Escherichia coli K-12: Gene-Enzyme Relationships and Intermediates

I G Young 1, P Stroobant 1, C G Macdonald 1, F Gibson 1
PMCID: PMC251738  PMID: 4572721

Abstract

Seven ubiquinone-deficient mutants of Escherichia coli, each of which accumulates two phenolic precursors of ubiquinone, have been characterized, and the accumulated compounds have been identified. The mutants accumulate small quantities of 2-octaprenyl-6-methoxyphenol, which was isolated and characterized by nuclear magnetic resonance and mass spectrometry, and relatively large amounts of 2-octaprenylphenol, a compound previously identified from E. coli. They also accumulate small quantities of a compound identified as 2-(hydroxyoctaprenyl)phenol although the relevance of this compound to the biosynthesis of ubiquinone is not clear. The results of genetic analysis suggest that each of the mutants carries a mutation in a gene (designated ubiH) which is located at about min 56 on the E. coli chromosome and is co-transducible with the serA and lysB genes. Based on information obtained from this and previous studies with ubiquinone-deficient mutants, a pathway is proposed for ubiquinone biosynthesis in E. coli, and a summary of the known gene-enzyme relationships is given.

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Selected References

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

  1. Bray H. G., Thorpe W. V., White K. The fate of certain organic acids and amides in the rabbit. 10. The application of paper chromatography to metabolic studies of hydroxybenzoic acids and amides. Biochem J. 1950 Mar;46(3):271–275. doi: 10.1042/bj0460271. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Cox G. B., Gibson F., Pittard J. Mutant strains of Escherichia coli K-12 unable to form ubiquinone. J Bacteriol. 1968 May;95(5):1591–1598. doi: 10.1128/jb.95.5.1591-1598.1968. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Cox G. B., Young I. G., McCann L. M., Gibson F. Biosynthesis of ubiquinone in Escherichia coli K-12: location of genes affecting the metabolism of 3-octaprenyl-4-hydroxybenzoic acid and 2-octaprenylphenol. J Bacteriol. 1969 Aug;99(2):450–458. doi: 10.1128/jb.99.2.450-458.1969. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. FOLCH J., LEES M., SLOANE STANLEY G. H. A simple method for the isolation and purification of total lipides from animal tissues. J Biol Chem. 1957 May;226(1):497–509. [PubMed] [Google Scholar]
  5. Hamilton J. A., Cox G. B. Ubiquinone biosynthesis in Escherichia coli K-12. Accumulation of an octaprenol, farnesylfarnesylgeraniol, by a multiple aromatic auxotroph. Biochem J. 1971 Jul;123(3):435–443. doi: 10.1042/bj1230435. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Imamoto S., Senoh S. Two new metabolites, 2- nonaprenylphenol and 2-nonaprenyl-3-methyl-6-methoxy-1, 4-benzoquinone, from Pseudomonas ovalis. Vox Sang. 1967 Jun;12(6):1237–1240. doi: 10.1016/s0040-4039(00)90675-0. [DOI] [PubMed] [Google Scholar]
  7. Jackman L. M., O'Brien I. G., Cox G. B., Gibson F. Methionine as the source of methyl groups for ubiquinone and vitamin K: a study using nuclear magnetic resonance and mass spectrometry. Biochim Biophys Acta. 1967 Jun 13;141(1):1–7. doi: 10.1016/0304-4165(67)90239-5. [DOI] [PubMed] [Google Scholar]
  8. Law A., Threlfall D. R., Whistance G. R. Isoprenoid phenol and quinone precursors of ubiguinones and dihydroubiguinones (ubiguinones (H 2 )) in fungi. Biochem J. 1971 Jul;123(3):331–339. doi: 10.1042/bj1230331. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Nowicki H. G., Dialameh G. H., Olson R. E. Isolation and identification of 6-methoxy-2-nonaprenylphenol as an intermediate in the biosynthesis of ubiquinone-9 in the rat. Biochemistry. 1972 Feb 29;11(5):896–904. doi: 10.1021/bi00755a032. [DOI] [PubMed] [Google Scholar]
  10. OLSEN R. K., SMITH J. L., DAVES G. D., MOORE H. W., FOLKERS K., PARSON W. W., RUDNEY H. 2-DECAPRENYLPHENOL, BIOSYNTHETIC PRECURSOR OF UBIQUINONE-10. J Am Chem Soc. 1965 May 20;87:2298–2300. doi: 10.1021/ja01088a045. [DOI] [PubMed] [Google Scholar]
  11. 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]
  12. PITTARD J. EFFECT OF INTEGRATED SEX FACTOR ON TRANSDUCTION OF CHROMOSOMAL GENES IN ESCHERICHIA COLI. J Bacteriol. 1965 Mar;89:680–686. doi: 10.1128/jb.89.3.680-686.1965. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Stroobant P., Young I. G., Gibson F. Mutants of Escherichia coli K-12 blocked in the final reaction of ubiquinone biosynthesis: characterization and genetic analysis. J Bacteriol. 1972 Jan;109(1):134–139. doi: 10.1128/jb.109.1.134-139.1972. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. TAYLOR A. L., THOMAN M. S. THE GENETIC MAP OF ESCHERICHIA COLI K-12. Genetics. 1964 Oct;50:659–677. doi: 10.1093/genetics/50.4.659. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Taylor A. L. Current linkage map of Escherichia coli. Bacteriol Rev. 1970 Jun;34(2):155–175. doi: 10.1128/br.34.2.155-175.1970. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Trumpower B. L., Aiyar A. S., Opliger C. E., Olson R. E. Studies on ubiquinone. The isolation and identification of 5-demethoxyubiquinone-9 as an intermediate in biosynthesis of ubiquinone-9 in the rat. J Biol Chem. 1972 Apr 25;247(8):2499–2511. [PubMed] [Google Scholar]
  17. Whistance G. R., Brown B. S., Threlfall D. R. Biosynthesis of ubiquinone in non-photosynthetic gram-negative bacteria. Biochem J. 1970 Mar;117(1):119–128. doi: 10.1042/bj1170119. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Whistance G. R., Field F. E., Threlfall D. R. Observations on the biosynthesis of ubiquinones by animals. Eur J Biochem. 1971 Jan 1;18(1):46–52. doi: 10.1111/j.1432-1033.1971.tb01212.x. [DOI] [PubMed] [Google Scholar]
  19. Young I. G., Leppik R. A., Hamilton J. A., Gibson F. Biochemical and genetic studies on ubiquinone biosynthesis in Escherichia coli K-12:4-hydroxybenzoate octaprenyltransferase. J Bacteriol. 1972 Apr;110(1):18–25. doi: 10.1128/jb.110.1.18-25.1972. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Young I. G., McCann L. M., Stroobant P., Gibson F. Characterization and genetic analysis of mutant strains of Escherichia coli K-12 accumulating the biquinone precursors 2-octaprenyl-6-methoxy-1,4-benzoquinone and 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone. J Bacteriol. 1971 Mar;105(3):769–778. doi: 10.1128/jb.105.3.769-778.1971. [DOI] [PMC free article] [PubMed] [Google Scholar]

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