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Pergantis SA, Wangkarn S, Francesconi KA, Thomas-Oates JE
Identification of arsenosugars at the picogram level using nanoelectrospray quadrupole time-of-flight mass spectrometry
Analytical Chemistry 72(2) (2000)
357-366
|
b-D-Sugf-(1-3)-Gro-(1-1)-Subst
Sug = bDRibf derivative = SMILES C[As](=O)(C)C[C@H]1O[C@@H](O)[C@H](O){1}[C@@H]1O;
Subst = SMILES O{1}S(O)=O |
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Sargassum lacerifolium
(NCBI TaxID 1197247,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: algae / Phaeophyceae
NCBI PubMed ID: 10658331Publication DOI: 10.1021/ac9906072Journal NLM ID: 0370536Correspondence: s.pergantis
chem.bbk.ac.uk
Institutions: Institute of Biology, University of Southern Denmark, Odense, Denmark, School of Biological and Chemical Sciences, Birkbeck College, University of London, London, UK, Michael Barber Centre for Mass Spectrometry, Department of Chemistry, University of Manchester Institute of Science and Technology, Manchester, UK
State-of-the-art analytical methods for arsenic speciation rely typically on the availability of standards of defined structure, limiting the applicability of such methods to the determination of known compounds. Our previous high-energy tandem mass spectrometric studies demonstrated the strength of mass spectrometry for generating structurally diagnostic ions that allow for the identification of arsenic-containing ribofuranosides (arsenosugars) without the use of standards. We now report a more widely applicable and more sensitive approach, using negative-ion nano-electrospray low-energy tandem mass spectrometry for the generation of structurally useful product ions that allow for identification of arsenosugars at the picogram level. In the negative-ion mode, numerous product ions, suitable for characterizing naturally occurring dimethylated arsenosugars, were generated in high abundance. Application of the method to an algal extract unequivocally demonstrated the presence of a single dimethylated arsenosugar. In the positive-ion mode, characteristic tandem mass spectra were obtained for four trimethylarsonioribosides, allowing their identification without the need for standards. Overall it was demonstrated that nano-ES-MS/MS techniques can be used for characterizing arsenosugars on a routine basis, a necessary requirement for assessing potential health risks associated with consuming foods containing elevated levels of arsenosugars and for improving our understanding of arsenic biochemistry.
arsenosugars, Sargassum lacerifolium, nESI-TOF-MS
Structure type: monomer
Location inside paper: p. 358, Fig. 1
Compound class: glycoside, arsenosugar
Methods: ESI-TOF/MS
Related record ID(s): 67350, 67351, 67352
NCBI Taxonomy refs (TaxIDs): 1197247
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There is only one chemically distinct structure:
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Pergantis SA, Wangkarn S, Francesconi KA, Thomas-Oates JE
Identification of arsenosugars at the picogram level using nanoelectrospray quadrupole time-of-flight mass spectrometry
Analytical Chemistry 72(2) (2000)
357-366
|
b-D-Sugf-(1-3)-Gro
Sug = bDRibf derivative = SMILES C[As](=O)(C)C[C@H]1O[C@@H](O)[C@H](O){1}[C@@H]1O |
Show graphically |
Sargassum lacerifolium
(NCBI TaxID 1197247,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: algae / Phaeophyceae
NCBI PubMed ID: 10658331Publication DOI: 10.1021/ac9906072Journal NLM ID: 0370536Correspondence: s.pergantis
chem.bbk.ac.uk
Institutions: Institute of Biology, University of Southern Denmark, Odense, Denmark, School of Biological and Chemical Sciences, Birkbeck College, University of London, London, UK, Michael Barber Centre for Mass Spectrometry, Department of Chemistry, University of Manchester Institute of Science and Technology, Manchester, UK
State-of-the-art analytical methods for arsenic speciation rely typically on the availability of standards of defined structure, limiting the applicability of such methods to the determination of known compounds. Our previous high-energy tandem mass spectrometric studies demonstrated the strength of mass spectrometry for generating structurally diagnostic ions that allow for the identification of arsenic-containing ribofuranosides (arsenosugars) without the use of standards. We now report a more widely applicable and more sensitive approach, using negative-ion nano-electrospray low-energy tandem mass spectrometry for the generation of structurally useful product ions that allow for identification of arsenosugars at the picogram level. In the negative-ion mode, numerous product ions, suitable for characterizing naturally occurring dimethylated arsenosugars, were generated in high abundance. Application of the method to an algal extract unequivocally demonstrated the presence of a single dimethylated arsenosugar. In the positive-ion mode, characteristic tandem mass spectra were obtained for four trimethylarsonioribosides, allowing their identification without the need for standards. Overall it was demonstrated that nano-ES-MS/MS techniques can be used for characterizing arsenosugars on a routine basis, a necessary requirement for assessing potential health risks associated with consuming foods containing elevated levels of arsenosugars and for improving our understanding of arsenic biochemistry.
arsenosugars, Sargassum lacerifolium, nESI-TOF-MS
Structure type: monomer
Location inside paper: p. 358, Fig. 1
Compound class: glycoside, arsenosugar
Methods: ESI-TOF/MS
Related record ID(s): 67349, 67351, 67352
NCBI Taxonomy refs (TaxIDs): 1197247
Show glycosyltransferases
There is only one chemically distinct structure:
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Pergantis SA, Wangkarn S, Francesconi KA, Thomas-Oates JE
Identification of arsenosugars at the picogram level using nanoelectrospray quadrupole time-of-flight mass spectrometry
Analytical Chemistry 72(2) (2000)
357-366
|
b-D-Sugf-(1-3)-Gro-(1-S
Sug = bDRibf derivative = SMILES C[As](=O)(C)C[C@H]1O[C@@H](O)[C@H](O){1}[C@@H]1O |
Show graphically |
Sargassum lacerifolium
(NCBI TaxID 1197247,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: algae / Phaeophyceae
NCBI PubMed ID: 10658331Publication DOI: 10.1021/ac9906072Journal NLM ID: 0370536Correspondence: s.pergantis
chem.bbk.ac.uk
Institutions: Institute of Biology, University of Southern Denmark, Odense, Denmark, School of Biological and Chemical Sciences, Birkbeck College, University of London, London, UK, Michael Barber Centre for Mass Spectrometry, Department of Chemistry, University of Manchester Institute of Science and Technology, Manchester, UK
State-of-the-art analytical methods for arsenic speciation rely typically on the availability of standards of defined structure, limiting the applicability of such methods to the determination of known compounds. Our previous high-energy tandem mass spectrometric studies demonstrated the strength of mass spectrometry for generating structurally diagnostic ions that allow for the identification of arsenic-containing ribofuranosides (arsenosugars) without the use of standards. We now report a more widely applicable and more sensitive approach, using negative-ion nano-electrospray low-energy tandem mass spectrometry for the generation of structurally useful product ions that allow for identification of arsenosugars at the picogram level. In the negative-ion mode, numerous product ions, suitable for characterizing naturally occurring dimethylated arsenosugars, were generated in high abundance. Application of the method to an algal extract unequivocally demonstrated the presence of a single dimethylated arsenosugar. In the positive-ion mode, characteristic tandem mass spectra were obtained for four trimethylarsonioribosides, allowing their identification without the need for standards. Overall it was demonstrated that nano-ES-MS/MS techniques can be used for characterizing arsenosugars on a routine basis, a necessary requirement for assessing potential health risks associated with consuming foods containing elevated levels of arsenosugars and for improving our understanding of arsenic biochemistry.
arsenosugars, Sargassum lacerifolium, nESI-TOF-MS
Structure type: monomer
Location inside paper: p. 358, Fig. 1
Compound class: glycoside, arsenosugar
Methods: ESI-TOF/MS
Related record ID(s): 67349, 67350, 67352
NCBI Taxonomy refs (TaxIDs): 1197247
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
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Pergantis SA, Wangkarn S, Francesconi KA, Thomas-Oates JE
Identification of arsenosugars at the picogram level using nanoelectrospray quadrupole time-of-flight mass spectrometry
Analytical Chemistry 72(2) (2000)
357-366
|
b-D-Sugf-(1-3)-Gro-(1--P--3)--Gro
Sug = bDRibf derivative = SMILES C[As](=O)(C)C[C@H]1O[C@@H](O)[C@H](O){1}[C@@H]1O |
Show graphically |
Sargassum lacerifolium
(NCBI TaxID 1197247,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: algae / Phaeophyceae
NCBI PubMed ID: 10658331Publication DOI: 10.1021/ac9906072Journal NLM ID: 0370536Correspondence: s.pergantis
chem.bbk.ac.uk
Institutions: Institute of Biology, University of Southern Denmark, Odense, Denmark, School of Biological and Chemical Sciences, Birkbeck College, University of London, London, UK, Michael Barber Centre for Mass Spectrometry, Department of Chemistry, University of Manchester Institute of Science and Technology, Manchester, UK
State-of-the-art analytical methods for arsenic speciation rely typically on the availability of standards of defined structure, limiting the applicability of such methods to the determination of known compounds. Our previous high-energy tandem mass spectrometric studies demonstrated the strength of mass spectrometry for generating structurally diagnostic ions that allow for the identification of arsenic-containing ribofuranosides (arsenosugars) without the use of standards. We now report a more widely applicable and more sensitive approach, using negative-ion nano-electrospray low-energy tandem mass spectrometry for the generation of structurally useful product ions that allow for identification of arsenosugars at the picogram level. In the negative-ion mode, numerous product ions, suitable for characterizing naturally occurring dimethylated arsenosugars, were generated in high abundance. Application of the method to an algal extract unequivocally demonstrated the presence of a single dimethylated arsenosugar. In the positive-ion mode, characteristic tandem mass spectra were obtained for four trimethylarsonioribosides, allowing their identification without the need for standards. Overall it was demonstrated that nano-ES-MS/MS techniques can be used for characterizing arsenosugars on a routine basis, a necessary requirement for assessing potential health risks associated with consuming foods containing elevated levels of arsenosugars and for improving our understanding of arsenic biochemistry.
arsenosugars, Sargassum lacerifolium, nESI-TOF-MS
Structure type: monomer
Location inside paper: p. 358, Fig. 1
Compound class: glycoside, arsenosugar
Contained glycoepitopes: IEDB_130695
Methods: ESI-TOF/MS
Related record ID(s): 67349, 67350, 67351
NCBI Taxonomy refs (TaxIDs): 1197247
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
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