TY - JOUR
T1 - Synthesis of anaerobic degradation biomarkers alkyl-, aryl- and cycloalkylsuccinic acids and their mass spectral characteristics
AU - Bian, Xin Yu
AU - Mbadinga, Serge Maurice
AU - Yang, Shi Zhong
AU - Gu, Ji Dong
AU - Ye, Ru Qiang
AU - Mu, Bo Zhong
PY - 2014
Y1 - 2014
N2 - Anaerobic biodegradation of petroleum hydrocarbons has been reported to proceed predominantly via fumarate addition to yield substitutedsuccinate metabolites. These metabolites, commonly regarded as signature biomarkers, are specific indicators of anaerobic hydrocarbon degradation by microbial activity. To the best of our knowledge, mass spectrometry information for 2-(1-methylalkyl) succinic acids, 2-arylsuccinic acids, 2-cycloalkylsuccinic acids and/or their derivatives is still incomplete, especially for the analysis of environmental samples. Here, a novel approach is proposed for the successful synthesis of five hydrocarbon-derived succinic acids. The characteristic fragments of 2-(1-methylalkyl)succinic acid diesters were investigated by four derivatization processes (methyl, ethyl, n-butyl and trimethylsilylesterification), some of which are not available in official libraries. Under electron ionization mass spectrometry conditions, informative fragments of various molecular masses have been obtained. Results confirmed characteristic differences among the derivatization processes of the chemically synthesized compounds. In the case of 2-(cyclo)alkylsuccinate esters, four intermediatefragments were observed at m/z 114 + 14n, 118 + 28n, [M - (17 + 14n)]+ and [M - (59 + 14n)]+ (n = 1, 2 and 4 for methyl, ethyl and n-butyl ester). However, for silylation the abundant fragment ions are at m/z 262, 217, 172, 147, 73 and [M - 15]+. These data provide information for the identification of hydrocarbon-derived succinic acids as anaerobic biodegradation intermediates in hydrocarbonsrich environments.
AB - Anaerobic biodegradation of petroleum hydrocarbons has been reported to proceed predominantly via fumarate addition to yield substitutedsuccinate metabolites. These metabolites, commonly regarded as signature biomarkers, are specific indicators of anaerobic hydrocarbon degradation by microbial activity. To the best of our knowledge, mass spectrometry information for 2-(1-methylalkyl) succinic acids, 2-arylsuccinic acids, 2-cycloalkylsuccinic acids and/or their derivatives is still incomplete, especially for the analysis of environmental samples. Here, a novel approach is proposed for the successful synthesis of five hydrocarbon-derived succinic acids. The characteristic fragments of 2-(1-methylalkyl)succinic acid diesters were investigated by four derivatization processes (methyl, ethyl, n-butyl and trimethylsilylesterification), some of which are not available in official libraries. Under electron ionization mass spectrometry conditions, informative fragments of various molecular masses have been obtained. Results confirmed characteristic differences among the derivatization processes of the chemically synthesized compounds. In the case of 2-(cyclo)alkylsuccinate esters, four intermediatefragments were observed at m/z 114 + 14n, 118 + 28n, [M - (17 + 14n)]+ and [M - (59 + 14n)]+ (n = 1, 2 and 4 for methyl, ethyl and n-butyl ester). However, for silylation the abundant fragment ions are at m/z 262, 217, 172, 147, 73 and [M - 15]+. These data provide information for the identification of hydrocarbon-derived succinic acids as anaerobic biodegradation intermediates in hydrocarbonsrich environments.
KW - 2-(1-methylalkyl)succinic acid
KW - 2-benzylsuccinic acid
KW - Anaerobic degradation
KW - Mass spectral characteristics
KW - Synthesis of biomarkers
UR - http://www.scopus.com/inward/record.url?scp=84929312901&partnerID=8YFLogxK
U2 - 10.1255/ejms.1280
DO - 10.1255/ejms.1280
M3 - 文章
C2 - 25420341
AN - SCOPUS:84929312901
SN - 1469-0667
VL - 20
SP - 287
EP - 297
JO - European Journal of Mass Spectrometry
JF - European Journal of Mass Spectrometry
IS - 4
ER -