Synthesis and mass spectra of rearrangement bio-signature metabolites of anaerobic alkane degradation via fumarate addition

Jing Chen, Lei Zhou, Yi Fan Liu, Zhao Wei Hou, Wei Li, Serge Maurice Mbadinga, Jing Zhou, Tao Yang, Jin Feng Liu, Shi Zhong Yang, Xiao Lin Wu, Ji Dong Gu, Bo Zhong Mu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Metabolite profiling in anaerobic alkane biodegradation plays an important role in revealing activation mechanisms. Apart from alkylsuccinates, which are considered to be the usual biomarkers via fumarate addition, the downstream metabolites of C-skeleton rearrangement can also be regarded as biomarkers. However, it is difficult to detect intermediate metabolites in both environmental samples and enrichment cultures, resulting in lacking direct evidence to prove the occurrence of fumarate addition pathway. In this work, a synthetic method of rearrangement metabolites was established. Four compounds, namely, propylmalonic acid, 2-(2-methylbutyl)malonic acid, 2-(2-methylpentyl)malonic acid and 2-(2-methyloctyl)malonic acid, were synthesized and determined by four derivatization approaches. Besides, their mass spectra were obtained. Four characteristic ions were observed at m/z 133 + 14n, 160 + 28n, 173 + 28n and [M - (45 + 14n)]+ (n = 0 and 2 for ethyl and n-butyl esters, respectively). For methyl esterification, mass spectral features were m/z 132, 145 and [M - 31]+, while for silylation, fragments were m/z 73, 147, 217, 248, 261 and [M - 15]+. These data provide basis on identification of potential rearrangement metabolites in anaerobic alkane biodegradation via fumarate addition.

Original languageEnglish
Article number113746
JournalAnalytical Biochemistry
Volume600
DOIs
StatePublished - 1 Jul 2020
Externally publishedYes

Keywords

  • Alkylmalonic acids
  • Fumarate addition
  • Mass spectral characteristics
  • Rearrangement bio-signature metabolites
  • Synthesis of biomarkers

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