Bacillus amyloliquefaciens CotA degradation of the lignin model compound guaiacylglycerol-β-guaiacyl ether

Lett Appl Microbiol. 2018 Nov;67(5):491-496. doi: 10.1111/lam.13060. Epub 2018 Sep 19.

Abstract

The cotA gene from Bacillus amyloliquefaciens MN-13 was cloned and expressed in Escherichia coli Transetta. Nucleotide sequence analysis showed an open reading frame of 1542 bp encoding a polypeptide comprised of 513 amino acids. The degradation of lignin model compounds by recombinant CotA was investigated by HPLC-MS with guaiacylglycerol-β-guaiacyl ether as the substrate. The compounds including guaiacol, 3-(4-hydro-3-methoxyphenyl)-3-oxo-propanol and 4-hydro-3-methoxy acetophenone detected by HPLC-MS verified the rupture of β-O-4 bond and oxidation Cα bond of guaiacylglycerol-β-guaiacyl ether by CotA. 4-vinylguaiacol and 1-(4-hydroxy-3-methoxyl phenyl)-1-(2-methoxyl) phenoxyl ethylene were first time found in the degradation products of guaiacylglycerol-β-guaiacyl ether. The appearance of 4-vinylguaiacol and 4-hydro-3-methoxy acetophenone confirmed the cleavage of Cβ-Cγ bond. 1-(4-hydroxy-3-methoxyl phenyl)-2-(2-methoxyl) phenoxyl ethylene was coupled by the radical reaction of 4-vinylguaiacol with guaiacol. Otherwise, no corresponding degradation product was found to give a proof of cleavage of Cα-Cβ bond in guaiacylglycerol-β-guaiacyl ether by CotA.

Keywords: Bacillus amyloliquefaciens; HPLC-MS; degradation; lignin model compounds; recombinant CotA.

MeSH terms

  • Bacillus amyloliquefaciens / enzymology*
  • Bacillus amyloliquefaciens / genetics
  • Escherichia coli / genetics
  • Escherichia coli / metabolism
  • Guaiacol / analogs & derivatives
  • Guaiacol / metabolism
  • Guaifenesin / analogs & derivatives*
  • Guaifenesin / metabolism
  • Laccase / genetics
  • Laccase / metabolism*
  • Lignin / metabolism*
  • Mass Spectrometry
  • Oxidation-Reduction

Substances

  • Guaifenesin
  • Guaiacol
  • guaiacylglycerol-beta-guaiacyl ether
  • 4-vinylguaiacol
  • Lignin
  • Laccase

Associated data

  • GENBANK/KP292553
  • GENBANK/MH552410