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

doi:10.1016/j.ab.2020.113746

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 journal › Article › peer-review

4 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 language	English
Article number	113746
Journal	Analytical Biochemistry
Volume	600
DOIs	https://doi.org/10.1016/j.ab.2020.113746
State	Published - 1 Jul 2020
Externally published	Yes

Keywords

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

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10.1016/j.ab.2020.113746

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

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.",

keywords = "Alkylmalonic acids, Fumarate addition, Mass spectral characteristics, Rearrangement bio-signature metabolites, Synthesis of biomarkers",

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

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier Inc.",

year = "2020",

month = jul,

day = "1",

doi = "10.1016/j.ab.2020.113746",

language = "英语",

volume = "600",

journal = "Analytical Biochemistry",

issn = "0003-2697",

publisher = "Academic Press Inc.",

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TY - JOUR

T1 - Synthesis and mass spectra of rearrangement bio-signature metabolites of anaerobic alkane degradation via fumarate addition

AU - Chen, Jing

AU - Zhou, Lei

AU - Liu, Yi Fan

AU - Hou, Zhao Wei

AU - Li, Wei

AU - Mbadinga, Serge Maurice

AU - Zhou, Jing

AU - Yang, Tao

AU - Liu, Jin Feng

AU - Yang, Shi Zhong

AU - Wu, Xiao Lin

AU - Gu, Ji Dong

AU - Mu, Bo Zhong

PY - 2020/7/1

Y1 - 2020/7/1

N2 - 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.

AB - 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.

KW - Alkylmalonic acids

KW - Fumarate addition

KW - Mass spectral characteristics

KW - Rearrangement bio-signature metabolites

KW - Synthesis of biomarkers

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DO - 10.1016/j.ab.2020.113746

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AN - SCOPUS:85083882066

SN - 0003-2697

VL - 600

JO - Analytical Biochemistry

JF - Analytical Biochemistry

M1 - 113746

ER -

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

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Keywords

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