Liquid chromatography/tandem mass spectrometry of free base alkyl porphyrins for the characterization of the macrocyclic substituents in components of complex mixtures

Rosell-Melé, Antoni; Carter, James F.; Maxwell, James R.

doi:10.1002/(sici)1097-0231(19990415)13:7<568::aid-rcm525>3.0.co;2-j

Cited by 39 publications

(9 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, atmospheric pressure chemical ionisation liquid chromatography/multistage mass spectrometry (APCI‐LC/MS n ), using an ion trap mass spectrometer, has been applied to the study of bchls c , d and e from bacterial cultures 10. The bchl e homologues were assigned unambiguously from their protonated molecules, and the fragmentations of the C‐8 and C‐12 alkyl substituents were consistent with the observations for the alkyl porphyrins 13. For the bchls c and d , although losses that were indicative of different C‐8 and C‐12 alkyl substituents were observed, it was not possible to determine the precise structure of each component beyond their assignment as one of two isobaric structural isomers.…”

supporting

confidence: 56%

“…The most abundant ion ( m/z 408; Fig. 4(a)) arises from the loss of 29 Da, corresponding to α ‐cleavage of Et, β ‐cleavage of n ‐Pr, or a combination of the two: each is the more highly favoured cleavage for the alkyl groups in question 10, 13. This strongly indicates that the alkylation pattern is [ n ‐Pr,Et], as a loss of 29 Da from [ i ‐Bu,Me] would be impossible.…”

Section: Resultsmentioning

confidence: 99%

“…MS n fragmentation studies of BPMEs c and d have the potential to reveal the alkylation pattern at C‐8 and C‐12 of the macrocycle. A study of the tandem mass spectral fragmentation behaviour of free‐base alkyl porphyrins showed that the alkyl substituents fragment by homolytic cleavage, resulting in the loss of alkyl radicals 13. It was noted that methyl and ethyl substituents preferentially fragment α to the macrocycle, resulting in losses of 15 and 29 Da, respectively.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Atmospheric pressure chemical ionisation liquid chromatography/multistage mass spectrometry for assignment of sedimentary bacteriochlorophyll derivatives

Wilson

Hodgson

Keely

2004

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Atmospheric pressure chemical ionisation liquid chromatography/multistage mass spectrometry (APCI-LC/MSn) provides a rapid, on-line method for the assignment of individual bacteriophaeophorbide c and d methyl esters (BPMEs) in complex mixtures. The MS2 spectrum for each component is diagnostic of the type of BPME (c or d), and characteristic losses in MS5 and MS6 permit assignment of the alkyl substituents at positions C-8 and C-12 of the macrocycle. MS5 mass chromatograms permit the deconvolution of coeluting isobaric BPMEs, revealing the true profiles of the individual components. The distributions are different in lake sediments from la Salada de Chiprana (Spain) and Kirisjes Pond (Antarctica), and a novel BPME c with a neo-pentyl substituent has been observed in the Kirisjes Pond sediment.

show abstract

supporting

confidence: 56%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Atmospheric pressure chemical ionisation liquid chromatography/multistage mass spectrometry for assignment of sedimentary bacteriochlorophyll derivatives

Wilson

Hodgson

Keely

2004

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

show abstract

“…However, APCI still suffers some degree of fragmentation, which is presumed to result from the collision of molecules at atmospheric pressure. 104,105 Electrospray ionization (ESI) of metalloporphyrins. Rodgers et al 30 first applied positive ion ESI FT-ICR MS to identify metalloporphyrins in a Venezuelan heavy oil (Cerro Negro) isolated via column chromatography.…”

Section: ■ Ionization Techniques For Ms Of Metalloporphyrinsmentioning

confidence: 99%

“…Soft ionization methods such as ESI, APCI, and APPI have shown promising results for the intact ionization of nickel/vanadyl porphyrins. However, APCI still suffers some degree of fragmentation, which is believed to be the result of collision of molecules at atmospheric pressure. , …”

Section: Ionization Techniques For Ms Of Metalloporphyrinsmentioning

confidence: 99%

Advances and Challenges in the Molecular Characterization of Petroporphyrins

et al. 2021

View full text Add to dashboard Cite

Petroporphyrins, geoporphyrins, or metalloporphyrins are the original petroleum biomarkers, identified by Alfred Treibs more than a century ago and the first molecular evidence for the biogenic origins of petroleum. Since discovery, analytical strategies have been developed to identify porphyrins in petroleum and its fractions. This review focuses on the advances enabled by ultrahigh resolving power Fourier transform ion cyclotron resonance mass spectrometry in tribute to Professor Alan G. Marshall.

show abstract

Electrospray ionization mass spectrometric analyses of rhodium tetraphenylporphyrin complexes as electrocatalysts for CO oxidation by tandem mass spectrometry and hyphenated method with capillary electrophoresis

Takeda

Yamazaki

2010

Rapid Commun. Mass Spectrom.

View full text Add to dashboard Cite

Carbon monoxide (CO) poisoning of platinum (Pt)-based electrocatalysts is a huge obstacle in the development of proton-exchange membrane fuel cells. Fuel cell performance can be improved by removing CO through electrolytic oxidation. Yamazaki et al. synthesized several rhodium (Rh) tetraphenylporphyrin complexes as electrocatalysts to reduce CO poisoning. Experimental results showed that these complexes display higher electrochemical CO oxidation activity than previously synthesized Rh octaethylporphyrin complex and that the differences in the structures of p-substituted groups influence their activity. To confirm the formation of these Rh tetraphenylporphyrin complexes, analyses were performed using electrospray ionization mass spectrometry (ESI-MS), electrospray ionization tandem mass spectrometry (ESI-MS/MS), and capillary electrophoresis-electrospray ionization mass spectrometry (CE-ESI-MS). In ESI-MS, peaks other than that of the Rh tetraphenylporphyrin complex were occasionally detected at different m/z values. The ESI-MS/MS and CE-ESI-MS results suggest that these peaks correspond to the complexes coordinating CO or other ions, or to remaining uncoordinated tetraphenylporphyrins. Coordination of CO is supported by the ESI-MS/MS results for the Rh octaethylporphyrin complex. Separation of the uncoordinated tetraphenylporphyrin from Rh tetraphenylporphyrin complex was achieved by CE-ESI-MS.

show abstract

Liquid chromatography/tandem mass spectrometry of free base alkyl porphyrins for the characterization of the macrocyclic substituents in components of complex mixtures

Cited by 39 publications

References 23 publications

Atmospheric pressure chemical ionisation liquid chromatography/multistage mass spectrometry for assignment of sedimentary bacteriochlorophyll derivatives

Atmospheric pressure chemical ionisation liquid chromatography/multistage mass spectrometry for assignment of sedimentary bacteriochlorophyll derivatives

Advances and Challenges in the Molecular Characterization of Petroporphyrins

Electrospray ionization mass spectrometric analyses of rhodium tetraphenylporphyrin complexes as electrocatalysts for CO oxidation by tandem mass spectrometry and hyphenated method with capillary electrophoresis

Contact Info

Product

Resources

About