Synthesis and characterization of anaerobic degradation biomarkers of n-alkanes via hydroxylation/carboxylation pathways

Jing Zhou, Xin-Yu Bian, Lei Zhou, Serge Maurice Mbadinga, Shi-Zhong Yang, Jin-Feng Liu, Ji-Dong Gu, Bo-Zhong Mu

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5 Scopus citations

Abstract

Metabolite profiling is a powerful method in research on anaerobic biodegradation of hydrocarbons. Hydroxylation and carboxylation are proposed pathways in anaerobic degradation but very little direct evidence is available about metabolites and signature biomarkers. 2-Acetylalkanoic acid is a potential signature metabolite because of its unique and specific structure among possible intermediates. A procedure for the synthesis of four homologues with various carbon chain lengths was proposed and the characteristics of 2-acetyl–alkanoic acid esters were investigated using four derivatization processes, namely methyl, ethyl, n-butyl and trimethylsilyl esterification. Four intermediate fragments observed were at m/z 73 + 14n, 87 + 14n, 102 + 14n (n = 1, 2 and 4 for methyl, ethyl and n-butyl ester, respectively) and [M − 42]+ for three of the derivatization methods. For silylation, characteristic ions were observed at m/z 73, 117, [M − 42]+ and [M − 55]+. These are basic and significant data for the future identification of potential intermediates of the hydroxylation and carboxylation pathways in hydrocarbon degradation.
Original languageEnglish
Pages (from-to)31-37
JournalEuropean Journal of Mass Spectrometry
DOIs
StatePublished - 1 Feb 2016
Externally publishedYes

Keywords

  • hydroxylation/carboxylation
  • potential biomarkers
  • 2-acetylalkanoic acid
  • synthesis of biomarkers
  • Mass spectral characteristics

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