메뉴 건너뛰기




Volumn 20, Issue 4, 2014, Pages 287-297

Synthesis of anaerobic degradation biomarkers alkyl-, aryl- and cycloalkylsuccinic acids and their mass spectral characteristics

Author keywords

2 (1 methylalkyl)succinic acid; 2 benzylsuccinic acid; Anaerobic degradation; Mass spectral characteristics; Synthesis of biomarkers

Indexed keywords

BIODEGRADATION; BIOMARKERS; ESTERS; MASS SPECTROMETRY; METABOLITES;

EID: 84929312901     PISSN: None     EISSN: 17516838     Source Type: Journal    
DOI: 10.1255/ejms.1280     Document Type: Article
Times cited : (14)

References (49)
  • 2
    • 34748892898 scopus 로고    scopus 로고
    • Bacterial metabolism of long-chain n-alkanes
    • doi :http://dx.doi.org/10.1007/s00253-007-1119-1
    • A. Wentzel, T. Ellingsen, H.K. Kotlar, S. Zotchev and M. Throne-Holst, "Bacterial metabolism of long-chain n-alkanes", Appl. Microbiol. Biot. 76, 1209 (2007). doi: http://dx.doi.org/10.1007/s00253-007-1119-1
    • (2007) Appl. Microbiol. Biot. , vol.76 , pp. 1209
    • Wentzel, A.1    Ellingsen, T.2    Kotlar, H.K.3    Zotchev, S.4    Throne-Holst, M.5
  • 4
    • 0025826944 scopus 로고
    • Anaerobic oxidationof saturated hydrocarbons to CO2 by a new type of sulfate-reducing bacterium
    • doi :http://dx.doi.org/10.1007/BF00418180
    • F. Aeckersberg, F. Bak and F. Widdel, "Anaerobic oxidationof saturated hydrocarbons to CO2 by a new type of sulfate-reducing bacterium", Arch. Microbiol. 156, 5 (1991). doi: http://dx.doi.org/10.1007/BF00418180
    • (1991) Arch. Microbiol. , vol.156 , pp. 5
    • Aeckersberg, F.1    Bak, F.2    Widdel, F.3
  • 5
    • 78650677445 scopus 로고    scopus 로고
    • Microbial communities involved in anaerobic degradation of alkanes
    • doi :http://dx.doi.org/10.1016/j.ibiod.2010.11.009
    • S.M. Mbadinga, L.Y. Wang, L. Zhou, J.F. Liu, J.D. Gu and B.Z. Mu, "Microbial communities involved in anaerobic degradation of alkanes", Int. Biodeter. Biodegr. 65, 1 (2011). doi: http://dx.doi.org/10.1016/j.ibiod. 2010.11.009
    • (2011) Int. Biodeter. Biodegr. , vol.65 , pp. 1
    • Mbadinga, S.M.1    Wang, L.Y.2    Zhou, L.3    Liu, J.F.4    Gu, J.D.5    Mu, B.Z.6
  • 6
    • 0031694750 scopus 로고    scopus 로고
    • Growth, naturalrelationships, cellular fatty acids and metabolic adaptation of sulfate-reducing bacteria that utilize longchain alkanes under anoxic conditions
    • doi :http://dx.doi.org/10.1007/s002030050654
    • F. Aeckersberg, F.A. Rainey and F. Widdel, "Growth, naturalrelationships, cellular fatty acids and metabolic adaptation of sulfate-reducing bacteria that utilize longchain alkanes under anoxic conditions", Arch. Microbiol. 170, 361 (1998). doi: http://dx.doi.org/10. 1007/ s002030050654
    • (1998) Arch. Microbiol. , vol.170 , pp. 361
    • Aeckersberg, F.1    Rainey, F.A.2    Widdel, F.3
  • 7
    • 0033984068 scopus 로고    scopus 로고
    • Anaerobic oxidation of alkanes by newly isolated denitrifyingbacteria
    • doi :http://dx.doi.org/10.1007/s002030050008
    • P. Ehrenreich, A. Behrends, J. Harder and F. Widdel, "Anaerobic oxidation of alkanes by newly isolated denitrifyingbacteria", Arch. Microbiol. 173, 58 (2000). doi: http://dx.doi.org/10.1007/s002030050008
    • (2000) Arch. Microbiol. , vol.173 , pp. 58
    • Ehrenreich, P.1    Behrends, A.2    Harder, J.3    Widdel, F.4
  • 8
    • 84866516898 scopus 로고    scopus 로고
    • Analysis of alkanedependent methanogenic community derived from production water of a high-temperature petroleum reservoir
    • doi :http://dx.doi.org/10.1007/s00253-011-3828-8
    • S.M. Mbadinga, K.-P. Li, L. Zhou, L.-Y. Wang, S.-Z. Yang, J.-F. Liu, J.-D. Gu and B.-Z. Mu, "Analysis of alkanedependent methanogenic community derived from production water of a high-temperature petroleum reservoir", Appl. Microbiol. Biot. 96, 531 (2012). doi: http://dx.doi.org/10.1007/s00253- 011-3828-8
    • (2012) Appl. Microbiol. Biot. , vol.96 , pp. 531
    • Mbadinga, S.M.1    Li, K.-P.2    Zhou, L.3    Wang, L.-Y.4    Yang, S.-Z.5    Liu, J.-F.6    Gu, J.-D.7    Mu, B.-Z.8
  • 9
    • 84884263262 scopus 로고    scopus 로고
    • Enzymes involved in the anaerobic oxidation of n-alkanes: From methane to long-chain paraffins
    • doi :http://dx.doi.org/10.3389/fmicb.2013.00089
    • A.V. Callaghan, "Enzymes involved in the anaerobic oxidation of n-alkanes: from methane to long-chain paraffins", Front. Microbiol. 4, 89 (2013). doi: http://dx.doi.org/10.3389/fmicb.2013.00089
    • (2013) Front. Microbiol. , vol.4 , pp. 89
    • Callaghan, A.V.1
  • 10
    • 84884270351 scopus 로고    scopus 로고
    • In situ detection of anaerobic alkane metabolites in subsurface environments
    • doi :http://dx.doi.org/10.3389/ fmicb.2013.00140
    • A. Agrawal and L.M. Gieg, "In situ detection of anaerobic alkane metabolites in subsurface environments", Front. Microbiol. 4, 140 (2013). doi: http://dx.doi.org/10.3389/ fmicb.2013.00140
    • (2013) Front. Microbiol. , vol.4 , pp. 140
    • Agrawal, A.1    Gieg, L.M.2
  • 11
    • 0031024020 scopus 로고    scopus 로고
    • Anaerobic activation of toluene and o-xylene by addition to fumarate in denitrifyingstrain T
    • H.R. Beller and A.M. Spormann, "Anaerobic activation of toluene and o-xylene by addition to fumarate in denitrifyingstrain T", J. Bacteriol. 179, 670 (1997).
    • (1997) J. Bacteriol. , vol.179 , pp. 670
    • Beller, H.R.1    Spormann, A.M.2
  • 12
    • 0030822679 scopus 로고    scopus 로고
    • Benzylsuccinate formation as a means of anaerobic toluene activation by sulfate-reducing strain PRTOL1
    • H.R. Beller and A.M. Spormann, "Benzylsuccinate formation as a means of anaerobic toluene activation by sulfate-reducing strain PRTOL1", Appl. Environ. Microbiol. 63, 3729 (1997).
    • (1997) Appl. Environ. Microbiol. , vol.63 , pp. 3729
    • Beller, H.R.1    Spormann, A.M.2
  • 13
    • 0034468016 scopus 로고    scopus 로고
    • Anaerobic toluene activationby benzylsuccinate synthase in a highly enriched methanogenic culture
    • doi :http://dx.doi.org/10.1128/ aem.66.12.5503-5505.2000
    • H.R. Beller and E.A. Edwards, "Anaerobic toluene activationby benzylsuccinate synthase in a highly enriched methanogenic culture", Appl. Environ. Microbiol. 66, 5503 (2000). doi: http://dx.doi.org/10.1128/ aem.66.12.5503-5505.2000
    • (2000) Appl. Environ. Microbiol. , vol.66 , pp. 5503
    • Beller, H.R.1    Edwards, E.A.2
  • 14
    • 0034468801 scopus 로고    scopus 로고
    • Anaerobic degradation of 2-methylnaphthalene by a sulfate-reducing enrichment culture
    • doi :http://dx.doi.org/10.1128/ aem.66.12.5329-5333.2000
    • E. Annweiler, A. Materna, M. Safinowski, A. Kappler, H.H. Richnow, W. Michaelis and R.U. Meckenstock, "Anaerobic degradation of 2-methylnaphthalene by a sulfate-reducing enrichment culture", Appl. Environ. Microbiol. 66, 5329 (2000). doi: http://dx.doi.org/10.1128/ aem.66.12.5329-5333.2000
    • (2000) Appl. Environ. Microbiol. , vol.66 , pp. 5329
    • Annweiler, E.1    Materna, A.2    Safinowski, M.3    Kappler, A.4    Richnow, H.H.5    Michaelis, W.6    Meckenstock, R.U.7
  • 15
    • 0035110830 scopus 로고    scopus 로고
    • Anaerobic initial reaction of n-alkanes in a denitrifying bacterium: Evidencefor (1-methylpentyl)succinate as initial product and for involvement of an organic radical in n-hexane metabolism
    • doi :http://dx.doi.org/10.1128/jb.183.5.1707-1715.2001
    • R. Rabus, H. Wilkes, A. Behrends, A. Armstroff, T. Fischer, A.J. Pierik and F. Widdel, "Anaerobic initial reaction of n-alkanes in a denitrifying bacterium: evidencefor (1-methylpentyl)succinate as initial product and for involvement of an organic radical in n-hexane metabolism", J. Bacteriol. 183, 1707 (2001). doi: http://dx.doi.org/10.1128/jb.183.5.1707-1715.2001
    • (2001) J. Bacteriol. , vol.183 , pp. 1707
    • Rabus, R.1    Wilkes, H.2    Behrends, A.3    Armstroff, A.4    Fischer, T.5    Pierik, A.J.6    Widdel, F.7
  • 17
    • 84884270351 scopus 로고    scopus 로고
    • In situ detection of anaerobic alkane metabolites in subsurface environments
    • doi :http://dx.doi.org/10.3389/ fmicb.2013.00140
    • L. Gieg and A. Agrawal, "In situ detection of anaerobic alkane metabolites in subsurface environments", Front. Microbiol. 4, 140 (2013). doi: http://dx.doi.org/10.3389/ fmicb.2013.00140
    • (2013) Front. Microbiol. , vol.4 , pp. 140
    • Gieg, L.1    Agrawal, A.2
  • 18
    • 79957985337 scopus 로고    scopus 로고
    • Anaerobic degradationof non-substituted aromatic hydrocarbons
    • doi :http://dx.doi.org/10.1016/j.copbio.2011.02.009
    • R.U. Meckenstock and H. Mouttaki, "Anaerobic degradationof non-substituted aromatic hydrocarbons", Curr. Opin. Biotech. 22, 406 (2011). doi: http://dx.doi.org/10.1016/j.copbio.2011.02.009
    • (2011) Curr. Opin. Biotech. , vol.22 , pp. 406
    • Meckenstock, R.U.1    Mouttaki, H.2
  • 19
    • 84878642895 scopus 로고    scopus 로고
    • Metabolomic investigations of anaerobic hydrocarbon-impacted environments
    • doi :http://dx.doi.org/10.1016/j. copbio.2012.08.012
    • A.V. Callaghan, "Metabolomic investigations of anaerobic hydrocarbon-impacted environments", Curr. Opin. Biotech. 24, 506 (2013). doi: http://dx.doi.org/10.1016/j. copbio.2012.08.012
    • (2013) Curr. Opin. Biotech. , vol.24 , pp. 506
    • Callaghan, A.V.1
  • 20
    • 0042859855 scopus 로고    scopus 로고
    • Formation of n-alkane- and cycloalkane-derived organic acids during anaerobic growth of a denitrifying bacterium with crude oil
    • doi :http://dx.doi.org/10.1016/ s0146-6380(03)00099-8
    • H. Wilkes, S. Kuhner, C. Bolm, T. Fischer, A. Classen, F. Widdel and R. Rabus, "Formation of n-alkane- and cycloalkane-derived organic acids during anaerobic growth of a denitrifying bacterium with crude oil", Org. Geochem. 34, 1313 (2003). doi: http://dx.doi.org/10.1016/ s0146-6380(03)00099-8
    • (2003) Org. Geochem. , vol.34 , pp. 1313
    • Wilkes, H.1    Kuhner, S.2    Bolm, C.3    Fischer, T.4    Classen, A.5    Widdel, F.6    Rabus, R.7
  • 21
    • 77956999086 scopus 로고    scopus 로고
    • Microbial nitrate-dependent cyclohexane degradationcoupled with anaerobic ammonium oxidation
    • doi :http://dx.doi.org/10.1038/ismej.2010.50
    • F. Musat, H. Wilkes, A. Behrends, D. Woebken and F. Widdel, "Microbial nitrate-dependent cyclohexane degradationcoupled with anaerobic ammonium oxidation", ISME J. 4, 1290 (2010). doi: http://dx.doi.org/10. 1038/ismej.2010.50
    • (2010) ISME J. , vol.4 , pp. 1290
    • Musat, F.1    Wilkes, H.2    Behrends, A.3    Woebken, D.4    Widdel, F.5
  • 22
    • 0036712646 scopus 로고    scopus 로고
    • Detection of anaerobic metabolites of saturated and aromatic hydrocarbons in petroleum-contaminated aquifers
    • doi :http://dx.doi.org/10.1021/ es0205333
    • L.M. Gieg and J.M. Suflita, "Detection of anaerobic metabolites of saturated and aromatic hydrocarbons in petroleum-contaminated aquifers", Environ. Sci. Technol. 36, 3755 (2002). doi: http://dx.doi.org/10.1021/ es0205333
    • (2002) Environ. Sci. Technol. , vol.36 , pp. 3755
    • Gieg, L.M.1    Suflita, J.M.2
  • 23
    • 78651392390 scopus 로고    scopus 로고
    • Metabolites indicate hot spots of biodegradation and biogeochemicalgradients in a high-resolution monitoring well
    • doi :http://dx.doi.org/10.1021/es1030867
    • C. Jobelius, B. Ruth, C. Griebler, R.U. Meckenstock, J. Hollender, A. Reineke, F.H. Frimmel and C. Zwiener, "Metabolites indicate hot spots of biodegradation and biogeochemicalgradients in a high-resolution monitoring well", Environ. Sci. Technol. 45, 474 (2010). doi: http://dx.doi.org/10. 1021/es1030867
    • (2010) Environ. Sci. Technol. , vol.45 , pp. 474
    • Jobelius, C.1    Ruth, B.2    Griebler, C.3    Meckenstock, R.U.4    Hollender, J.5    Reineke, A.6    Frimmel, F.H.7    Zwiener, C.8
  • 24
    • 70450218710 scopus 로고    scopus 로고
    • Biocorrosive thermophilic microbial communities in Alaskan north slope oil facilities
    • doi :http://dx.doi.org/10.1021/es9013932
    • K.E. Duncan, L.M. Gieg, V.A. Parisi, R.S. Tanner, S.G. Tringe, J. Bristow and J.M. Suflita, "Biocorrosive thermophilic microbial communities in Alaskan north slope oil facilities", Environ. Sci. Technol. 43, 7977 (2009). doi: http://dx.doi.org/10.1021/es9013932
    • (2009) Environ. Sci. Technol. , vol.43 , pp. 7977
    • Duncan, K.E.1    Gieg, L.M.2    Parisi, V.A.3    Tanner, R.S.4    Tringe, S.G.5    Bristow, J.6    Suflita, J.M.7
  • 25
    • 0034466705 scopus 로고    scopus 로고
    • Anaerobic oxidation of n-dodecane by an addition reaction in a sulfate-reducing bacterial enrichment culture
    • doi:http://dx.doi.org/10.1128/aem.66.12.5393-5398.2000
    • K.G. Kropp, I.A. Davidova and J.M. Suflita, "Anaerobic oxidation of n-dodecane by an addition reaction in a sulfate-reducing bacterial enrichment culture", Appl. Environ. Microbiol. 66, 5393 (2000). doi: http://dx.doi.org/10.1128/aem.66.12.5393-5398.2000
    • (2000) Appl. Environ. Microbiol. , vol.66 , pp. 5393
    • Kropp, K.G.1    Davidova, I.A.2    Suflita, J.M.3
  • 26
    • 84856444621 scopus 로고    scopus 로고
    • Stereochemical investigations reveal the mechanism of the bacterial activation of n-alkanes without oxygen
    • doi :http://dx.doi.org/10.1002/anie.201106055
    • R. Jarling, M. Sadeghi, M. Drozdowska, S. Lahme, W. Buckel, R. Rabus, F. Widdel, B. Golding and H. Wilkes, "Stereochemical investigations reveal the mechanism of the bacterial activation of n-alkanes without oxygen", Angew. Chem. Int. Ed. 51, 1334 (2012). doi: http://dx.doi.org/10.1002/anie.201106055
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1334
    • Jarling, R.1    Sadeghi, M.2    Drozdowska, M.3    Lahme, S.4    Buckel, W.5    Rabus, R.6    Widdel, F.7    Golding, B.8    Wilkes, H.9
  • 27
    • 67649922798 scopus 로고    scopus 로고
    • Assessing in situ rates of anaerobic hydrocarbon bioremediation
    • doi :http://dx.doi.org/10.1111/j.1751-7915.2008.00081.x
    • L.M. Gieg, R.E. Alumbaugh, J. Field, J. Jones, J.D. Istok and J.M. Suflita, "Assessing in situ rates of anaerobic hydrocarbon bioremediation", Microb. Biotechnol. 2, 222 (2009). doi: http://dx.doi.org/10.1111/j.1751-7915.2008.00081.x
    • (2009) Microb. Biotechnol. , vol.2 , pp. 222
    • Gieg, L.M.1    Alumbaugh, R.E.2    Field, J.3    Jones, J.4    Istok, J.D.5    Suflita, J.M.6
  • 28
    • 33745171431 scopus 로고    scopus 로고
    • Comparison of mechanisms of alkane metabolism under sulfate-reducing conditions among two bacterial isolates and a bacterial consortium
    • doi :http://dx.doi.org/10.1128/aem.02896-05
    • A.V. Callaghan, L.M. Gieg, K.G. Kropp, J.M. Suflita and L.Y. Young, "Comparison of mechanisms of alkane metabolism under sulfate-reducing conditions among two bacterial isolates and a bacterial consortium", Appl. Environ. Microbiol. 72, 4274 (2006). doi: http://dx.doi.org/10.1128/aem.02896-05
    • (2006) Appl. Environ. Microbiol. , vol.72 , pp. 4274
    • Callaghan, A.V.1    Gieg, L.M.2    Kropp, K.G.3    Suflita, J.M.4    Young, L.Y.5
  • 29
    • 0025968308 scopus 로고    scopus 로고
    • An efficient synthesis of optically active 2-alkylsuccinate monoesters
    • doi :http://dx.doi.org/10.1055/s-1991-26405
    • M. Larcheveque and Y. Petit, "An efficient synthesis of optically active 2-alkylsuccinate monoesters", Synthesis. 1991, 162 (2002). doi: http://dx.doi.org/10.1055/s-1991-26405
    • (2002) Synthesis. , vol.1991 , pp. 162
    • Larcheveque, M.1    Petit, Y.2
  • 30
    • 84940326868 scopus 로고
    • Ethyl n-butylmalonate
    • A. Roger and K. RM, "Ethyl n-butylmalonate", Org. Synth. 4, 11 (1925).
    • (1925) Org. Synth. , vol.4 , pp. 11
    • Roger, A.1    Rm, K.2
  • 33
    • 83755214921 scopus 로고    scopus 로고
    • Rapid synthesisof flavor compound 4-ethyloctanoic acid under microwave irradiation
    • doi :http://dx.doi.org/10.3390/ijms11104165
    • Y.P. Liu, D.C. Yin, H.T. Chen and B.G. Sun, "Rapid synthesisof flavor compound 4-ethyloctanoic acid under microwave irradiation", Int. J. Mol. Sci. 11, 4165 (2010). doi: http://dx.doi.org/10.3390/ijms11104165
    • (2010) Int. J. Mol. Sci. , vol.11 , pp. 4165
    • Liu, Y.P.1    Yin, D.C.2    Chen, H.T.3    Sun, B.G.4
  • 34
    • 33947093954 scopus 로고
    • Synthetic applicationsand mechanism studies of the decarbalkoxylations of geminal diesters and related systems effected in dimethyl sulfoxide by water and/or by water with added salts
    • doi :http://dx.doi.org/10.1021/jo00395a032
    • A.P. Krapcho, J.F. Weimaster, J.M. Eldridge, E.G.E. Jahngen, A.J. Lovey and W.P. Stephens, "Synthetic applicationsand mechanism studies of the decarbalkoxylations of geminal diesters and related systems effected in dimethyl sulfoxide by water and/or by water with added salts", J. Org. Chem. 43, 138 (1978). doi: http://dx.doi.org/10.1021/jo00395a032
    • (1978) J. Org. Chem. , vol.43 , pp. 138
    • Krapcho, A.P.1    Weimaster, J.F.2    Eldridge, J.M.3    Jahngen, E.G.E.4    Lovey, A.J.5    Stephens, W.P.6
  • 36
    • 0036189978 scopus 로고    scopus 로고
    • Anaerobic degradation of n-hexane in a denitrifying bacterium: Further degradation of the initial intermediate (1-methylpentyl)succinate via C-skeleton rearrangement
    • doi :http://dx.doi.org/10.1007/s00203-001-0381-3
    • H. Wilkes, R. Rabus, T. Fischer, A. Armstroff, A. Behrends and F. Widdel, "Anaerobic degradation of n-hexane in a denitrifying bacterium: further degradation of the initial intermediate (1-methylpentyl)succinate via C-skeleton rearrangement", Arch. Microbiol. 177, 235 (2002). doi: http://dx.doi.org/10.1007/s00203-001-0381-3
    • (2002) Arch. Microbiol. , vol.177 , pp. 235
    • Wilkes, H.1    Rabus, R.2    Fischer, T.3    Armstroff, A.4    Behrends, A.5    Widdel, F.6
  • 37
    • 0347033276 scopus 로고    scopus 로고
    • Anaerobic degradation of ethylbenzene by a new type of marine sulfate-reducing bacterium
    • doi :http://dx.doi.org/10.1128/AEM.69.2.760-768.2003
    • O. Kniemeyer, T. Fischer, H. Wilkes, F.O. Glockner and F. Widdel, "Anaerobic degradation of ethylbenzene by a new type of marine sulfate-reducing bacterium", Appl. Environ. Microb. 69, 760 (2003). doi: http://dx.doi.org/10.1128/AEM.69.2.760-768.2003
    • (2003) Appl. Environ. Microb. , vol.69 , pp. 760
    • Kniemeyer, O.1    Fischer, T.2    Wilkes, H.3    Glockner, F.O.4    Widdel, F.5
  • 38
    • 84860413270 scopus 로고    scopus 로고
    • Co-metabolic conversion of toluene in anaerobic n-alkane-degrading bacteria
    • doi :http://dx.doi.org/10.1111/ j.1462-2920.2011.02529.x
    • R. Rabus, R. Jarling, S. Lahme, S. Kuhner, J. Heider, F. Widdel and H. Wilkes, "Co-metabolic conversion of toluene in anaerobic n-alkane-degrading bacteria", Environ. Microbiol. 13, 2576 (2011). doi: http://dx.doi.org/10. 1111/ j.1462-2920.2011.02529.x
    • (2011) Environ. Microbiol. , vol.13 , pp. 2576
    • Rabus, R.1    Jarling, R.2    Lahme, S.3    Kuhner, S.4    Heider, J.5    Widdel, F.6    Wilkes, H.7
  • 39
    • 29144499457 scopus 로고    scopus 로고
    • Stable isotopic studies of n-alkane metabolism by a sulfate-reducing bacterial enrichment culture
    • doi :http://dx.doi.org/10.1128/aem.71.12.8174-8182.2005
    • I.A. Davidova, L.M. Gieg, M. Nanny, K.G. Kropp and J.M. Suflita, "Stable isotopic studies of n-alkane metabolism by a sulfate-reducing bacterial enrichment culture", Appl. Environ. Microb. 71, 8174 (2005). doi: http://dx.doi.org/10.1128/aem.71.12.8174-8182.2005
    • (2005) Appl. Environ. Microb. , vol.71 , pp. 8174
    • Davidova, I.A.1    Gieg, L.M.2    Nanny, M.3    Kropp, K.G.4    Suflita, J.M.5
  • 41
    • 33847804321 scopus 로고
    • Intramolecular hydrogen transfer in mass spectra. II. McLafferty rearrangement and related reactions
    • doi :http://dx.doi.org/10.1021/ cr60288a004
    • D.G. Kingston, J.T. Bursey and M.M. Bursey, "Intramolecular hydrogen transfer in mass spectra. II. McLafferty rearrangement and related reactions", Chem. Rev. 74, 215 (1974). doi: http://dx.doi.org/10.1021/ cr60288a004
    • (1974) Chem. Rev. , vol.74 , pp. 215
    • Kingston, D.G.1    Bursey, J.T.2    Bursey, M.M.3
  • 42
    • 26144458653 scopus 로고    scopus 로고
    • An electron impact and chemical ionization study of some diethyl dicarboxylates
    • doi :http://dx.doi.org/10.1016/S0168-1176(97)00073-6
    • A.G. Harrison and J. Malat, "An electron impact and chemical ionization study of some diethyl dicarboxylates", Int. J. Mass Spectrom. 167, 213 (1997). doi: http://dx.doi.org/10.1016/S0168-1176(97)00073-6
    • (1997) Int. J. Mass Spectrom. , vol.167 , pp. 213
    • Harrison, A.G.1    Malat, J.2
  • 43
    • 49049123580 scopus 로고
    • Mass spectra of the dimethyl esters of some branched aliphatic a,wdicarboxylicacids
    • doi :http://dx.doi.org/10.1016/0020-7381(83) 87045-4
    • J. Pettersen and G. Hvistendahl, "Mass spectra of the dimethyl esters of some branched aliphatic a,wdicarboxylicacids", Int. J. Mass Spectrom. 48, 129 (1983). doi: http://dx.doi.org/10.1016/0020-7381(83)87045-4
    • (1983) Int. J. Mass Spectrom. , vol.48 , pp. 129
    • Pettersen, J.1    Hvistendahl, G.2
  • 44
    • 37049115238 scopus 로고
    • Methoxy-group migrations in the mass spectra of aliphatic dimethyl esters
    • doi :http://dx.doi.org/10.1039/C19670000733
    • I. Howe and D.H. Williams, "Methoxy-group migrations in the mass spectra of aliphatic dimethyl esters", Chem. Commun. 733 (1967). doi: http://dx.doi.org/10.1039/ C19670000733
    • (1967) Chem. Commun. , vol.733
    • Howe, I.1    Williams, D.H.2
  • 45
    • 26144458653 scopus 로고    scopus 로고
    • An electron impact and chemical ionization study of some diethyl dicarboxylates
    • doi :http://dx.doi.org/10.1016/S0168- 1176(97)00073-6
    • A.G. Harrison and J. Malat, "An electron impact and chemical ionization study of some diethyl dicarboxylates", Int. J. Mass Spectrom. Ion Processes. 167, 213 (1997). doi: http://dx.doi.org/10.1016/S0168- 1176(97)00073-6
    • (1997) Int. J. Mass Spectrom. Ion Processes. , vol.167 , pp. 213
    • Harrison, A.G.1    Malat, J.2
  • 46
    • 0038249323 scopus 로고
    • Mass spectrometry in structural and stereochemical problems. LXXXVI. The hydrogen-transfer reactions in butyl propionate, benzoate, and phthalate
    • doi :http://dx.doi.org/10.1021/ja00952a041
    • C. Djerassi and C. Fenselau, "mass spectrometry in structural and stereochemical problems. LXXXVI. The hydrogen-transfer reactions in butyl propionate, benzoate, and phthalate", J. Am. Chem. Soc. 87, 5756 (1965). doi: http://dx.doi.org/10.1021/ja00952a041
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 5756
    • Djerassi, C.1    Fenselau, C.2
  • 47
    • 4043107241 scopus 로고
    • Mass spectrometry in structural and stereochemical problems. CLV. Electron impact induced fragmentations and rearrangements of some trimethylsilyl ethers of aliphatic glycols, and related compounds
    • doi :http://dx.doi.org/10.1021/jo01270a022
    • J. Diekman, J.B. Thomson and C. Djerassi, "Mass spectrometry in structural and stereochemical problems. CLV. Electron impact induced fragmentations and rearrangements of some trimethylsilyl ethers of aliphatic glycols, and related compounds", J. Org. Chem. 33, 2271 (1968). doi: http://dx.doi.org/10.1021/jo01270a022
    • (1968) J. Org. Chem. , vol.33 , pp. 2271
    • Diekman, J.1    Thomson, J.B.2    Djerassi, C.3
  • 48
    • 84985437785 scopus 로고
    • Interaction and rearrangement of trimethylsilyloxy functional groups. The structural significance of the m/e 147 ion in the mass spectra of trimethylsil steroidal ethers
    • doi :http://dx.doi.org/10.1002/ oms.1210050705
    • S. Sloan, D.J. Harvey and P. Vouros, "Interaction and rearrangement of trimethylsilyloxy functional groups. The structural significance of the m/e 147 ion in the mass spectra of trimethylsil steroidal ethers", Org. Mass. Spectrom. 5, 789 (1971). doi: http://dx.doi.org/10.1002/ oms.1210050705
    • (1971) Org. Mass. Spectrom. , vol.5 , pp. 789
    • Sloan, S.1    Harvey, D.J.2    Vouros, P.3
  • 49
    • 84860413270 scopus 로고    scopus 로고
    • Co-metabolic conversion of toluene in anaerobic n-alkane-degrading bacteria
    • doi :http://dx.doi.org/10.1111/j.1462-2920.2011.02529.x
    • R. Rabus, R. Jarling, S. Lahme, S. Kuhner, J. Heider, F. Widdel and H. Wilkes, "Co-metabolic conversion of toluene in anaerobic n-alkane-degrading bacteria", Environ Microbiol. 13, 2576 (2011). doi: http://dx.doi.org/10. 1111/j.1462-2920.2011.02529.x
    • (2011) Environ Microbiol. , vol.13 , pp. 2576
    • Rabus, R.1    Jarling, R.2    Lahme, S.3    Kuhner, S.4    Heider, J.5    Widdel, F.6    Wilkes, H.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.