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Microbial production of specifically ring-13C-labelled 4-hydroxybenzoic acid

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Abstract

When transformed with a recombinant vector carrying the ubiC gene (encoding chorismate pyruvate-lyase, EC 4.1.3.27) the triple mutant (Phe, Trp, Tyr) Klebsiella pneumoniae 62-1 excretes 4-hydroxybenzoic acid instead of chorismic acid. The recombinant strain can be used to produce in high yield specifically ring-labelled 4-hydroxybenzoic acid from isotopically labelled glucose.

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References

  • Baldwin JE, Bausal HS, Chondrogianni J, Gallagher PT, Taha AA, Taylor A, Thaller V (1984) Synthesis of [15N], [1−13C], [3−13C], [ring−1, 2−13C2], and [ring-3, 4, 5−13C3], labelled DL-tyrosine. J Chem Res (Synop) 176−177

  • Bullock WO, Fernandez JM, Short JM (1987) XL1-Blue: a high efficiency plasmid transforming recA Escherichia coli strain with beta galactosidase selection. Biotechniques 5:376–378

    Google Scholar 

  • Floss HG, Keller PJ, Beale JM (1986) Studies on the biosynthesis of antibiotics. J Nat Prod 49:957–970

    Google Scholar 

  • Gibson J, Dispensa M, Fogg GC, Evans DT, Harwood CS (1994) 4-Hydroxybenzoate-coenzyme A ligase from Rhodopseudomonas palustris: purification, gene sequence, and role in anaerobic degradation. J Bacteriol 176:634–641

    Google Scholar 

  • Haslam E (1993) Shikimic acid-metabolism and metabolites. Wiley, Chichester

    Google Scholar 

  • Heide L, Tabata M (1987) Geranylpyrophosphate: p-hydroxybenzoate geranyltransferase activity in extracts of Lithospermum erythrorhizon cell cultures. Phytochemistry 26:1651–1655

    Google Scholar 

  • Inouye H, Leistner E (1988) vol. Biochemistry of quinones. In: Patai S., Rappoport Z (eds) The chemistry of quinonoid compounds, vol 2. Wiley, Chichester, pp 1294–1344

    Google Scholar 

  • Jurkova M, Wurst M (1993) Biodegradation of aromatic carboxylic acids by Pseudomonas mira. FEMS Microbiol Lett 11:245–250

    Google Scholar 

  • Kaneda T, Obata H, Tokumoto M (1993) Aromatization of 4-oxocylohexanecarboxylic acid to 4-hydroxybenzoic acid by two distinctive desaturases from Corynebacterium cyclohexanicum. Properties of two desaturases. Eur J Biochem 218:997–1003

    Google Scholar 

  • Löscher R, Heide L (1994) Biosynthesis of 4-hydroxybenzoate from p-coumarate and p-coumaroyl-coenzyme A in cell-free extracts of Lithospermum erythrorhizon cell cultures. Plant Physiol 106:271–279

    Google Scholar 

  • Niemann GJ (1995) A crucial role of phenolic metabolism in resistance of carnations to wilt diseases. Acta Hort (in press)

  • Nieβner N, Mühlebach A, Lyerla JR (1993) Synthesis of isotopically labelled monomers and polymers of 4-hydroxybenzoic acid and 6-hydroxy-2-naphthoic acid. Makromol Chem 194:649–663

    Google Scholar 

  • Nishimura A, Morita M, Nishimura Y, Sugino Y (1991) A rapid and highly efficient method for preparation of competent Escherichia coli cells. Nucleic Acids Res 18:6169

    Google Scholar 

  • Rajagopalan JS, Jaffe EK (1993) Microbial production and NMR characterization of [2, 6, 9−13C] chorismate and [1, 3, 5, 8−13C] chorismate. Bioorg Med Chem Lett 3:1453–1456

    Google Scholar 

  • Rusche J, Flanders PH (1985) Hexamin cobalt chloride promotors intermolecular ligation of blunt end DNA fragments by T4 DNA ligase. Nucleic Acids Res 13:1997–2008

    Google Scholar 

  • Schmid HV, Zenk MH (1971) p-hydroxybenzoic acid and mevalonic acid as precursors of the plant naphthoquinone alkannin. Tetrahedron Lett 44:4151–4155

    Google Scholar 

  • Schmidt K, Leistner E (1995) Microbial production of (+)-trans-isochorismic acid. Biotechnol Bioeng 45:285–291

    Google Scholar 

  • Siebert M, Bechthold A, Melzer M, May U, Berger U, Schröder G, Schröder J, Serverin K, Heide L (1992) Ubiquinone biosynthesis. Cloning of the genes for chorismate pyruvate-lyase and 4-hydroxybenzoate octaprenyl transferase from Escherichia coli. FEBS Lett 307:347–350

    Google Scholar 

  • Siebert M, Severin K, Heide L (1994) Formation of 4-hydroxybenzoate in Escherichia coli: characterization of the ubiC gene and its encoded enzyme chorismate pyruvate-lyase, Microbiology 140:897–904

    Google Scholar 

  • Spratt BG, Hedge PJ, te Heesen S, Edelman A, Broome-Smith JK (1986) Kanamycin resistant vectors that are analogous of plasmids pUC8, pUC9, pEMBL8 and pEMBL9. Gene 41:337–342

    Google Scholar 

  • Vogel HJ, Bonner DM (1956) Acetylornithase of Escherichia coli: partial purification and some properties. J Biol Chem 218:97–106

    Google Scholar 

  • Zenk MH (1964) Einbau von p-Hydroxybenzoesäure in die Hydrochinonkomponente des Arbutins in Bergenia crassifolia. Z Naturforsch [B] 19:856–857

    Google Scholar 

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Müller, R., Wagener, A., Schmidt, K. et al. Microbial production of specifically ring-13C-labelled 4-hydroxybenzoic acid. Appl Microbiol Biotechnol 43, 985–988 (1995). https://doi.org/10.1007/BF00166913

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  • DOI: https://doi.org/10.1007/BF00166913

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