1. synthesis of selenated hydroxy fatty acids brasinoe u
DESCRIPTION
formulamass*error, ppm triglyceridemodification* theoreticalexperimental C 57 H 100 O 12 Se 2 C 57 H 100 O 11 Se C 57 H 100 O 9 Se C 57 H 100 O 10 Se C 57 H 98 O 9 Se C 57 H 98 O 8 Se C 57 H 102 O 12 Se 2 C 57 H 10 2O 9 Se , , , , , ,6547 0,08 0,79 1,19 0,96 1,62 -0,01 -2,41 -3,35 LLO LLL LLO LLL OOO LLO LOO Species identification * masses correspond to [M+Na] + except C 57 H 98 O 8 Se ** modifications: In selol molecules we have observed 4 repetitive modifications of structures containing selenium. BRASINO EUTRANSCRIPT
1. Synthesis of selenated hydroxy fatty acids
CO
HO
Hydroxylation(KMnO4; H+ in H2O)
CO
HO
HOOH
OHOH
Esterification
Se
CO
HO
OO
OO
SeO
O
(H2SeO3 in dioxane; catalyst )
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2. Speciation of selenium in selol 5%The second topic researched by our team is to examine the structure
of molecules of hydroxylated triglycerides containing selenium (IV).
In our research we use HPLC-ICP MS/ electrospray - Orbitrap MS/MS
techniques and 1H, 13C and 77Se NMR. We use hydroxylated and selenated standards obtained from trioleic
and trilinolenic glycerides.
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formula mass* error,ppm
triglyceride modification*theoretical experimental
C57H100O12Se2
C57H100O11SeC57H100O9SeC57H100O10SeC57H98O9SeC57H98O8SeC57H102O12Se2
C57H102O9Se
1159.54371063.63231031.64251047.63741029.62681013.63191049.65361033.6587
1159,54441063,63371031.64431047,63891029.62901013,63251049,65051033,6547
0,080,791,190,961,62-0,01-2,41-3,35
LLOLLLLLOLLLLLL
OOOLLOLOO
41323323
Species identification
*masses correspond to [M+Na]+ except C57H98O8Se**modifications:
In selol molecules we have observed 4 repetitive modifications of structures containing selenium.
HOOH
OO
Se
O
HO OO
Se
O
OO
Se
O
OO
Se
O
OO
Se
O1 2 3 4
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0 5 10 15 20 25
0 5 10 15 20 25
0 5 10 15 20 25
0 10 20 30 40 50 60
OH
O
CH3
SeO
O
CH3
Na+
O
CH3
O
O
O
O
O
O OO
ONa
OO
SeO
O
O
C57H98O9Se
C57H100O10Se
C57H100O11Se
trilinoleate derivatives
Retention time, min
(a)
HC
H2C
H2C O
O
O
C
C
CO
O
ONa
O OSe
O
OHHO
The panel presents HPLC-ICP MS chromatogram in order to demonstrate the matching of peaks obtained using elemental and molecular MS detection.
Extracted ion chromatograms (XICs) corresponding to the pseudomolecular ions containing one or more selenium atoms
Putative formula supported by MS2 and MS3 analysis.
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0 10 20 30 40 50 60
dilinoleate-monooleate derivatives
0 5 10 15 20 25
0 5 10 15 20 25
O
CH3
O
Na+
O
OSe
OO
CH3O
CH3O
O
HC
H2C
H2C O
O
O
C
C
CO
O
OONa
OSe
O
OO
SeO
C57H100O9Se
C57H100O12Se2
HC
H2C
H2C O
O
O
C
C
CO
O
ONa
OSe
O
HOO C57H102O10Se
Retention time, min
(b) The panel presents HPLC-ICP MS chromatogram in order to demonstrate matching of peaks obtained using elemental and molecular MS detection.
Extracted ion chromatograms (XICs) corresponding to the pseudomolecular ions containing one or more selenium atoms
Putative formula supported by MS2 and MS3 analysis.
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0 10 20 30 40 50 60
Retention time, min0 5 10 15 20 25
C57H104O9Se
monolinoleate-dioleate derivatives
trioleate derivative
C57H102O9Se
C57H102O9Se2
(c)
HC
H2C
H2C O
O
O
C
C
CO
O
ONa
OSe
O
O
HC
H2C
H2C O
O
O
C
C
CO
O
ONa
OSe
Se
O
O
O OO
OO
OSe
O
O
O
The panel presents HPLC-ICP MS chromatogram in order to demonstrate matching of peaks obtained using elemental and molecular MS detection.
Putative formula supported by MS2 and MS3 analysis.
Extracted ion chromatograms (XICs) corresponding to the pseudomolecular ions containing one or more selenium atoms
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O OO
OO
OSe
O
O
O
C57H104O9Se[M+H]+
C57H96O7Se[M+Na]+
C18H30O3Se[M+Na]+
O
SeOO
Na
OSe
OO
CH3
O
CH3
Na+
O
O
CH3
O
O
Se
O
CH3
CH2
Na+
O
O
CH3
O
MS3
MS3
C39H64O5Se[M+Na]+
C39H68O6Se[M+H]+
C18H32O4Se[M+Na]+
ONa
O
SeO
O
O
O
ONa
OO
SeO
MS3
OCH3
O
CH3
OSe
OO
O
O
CH3
OO
C56H96O9Se[M+H]+MS2 MS2
MS2
O
OO
SeHO
O
C57H106O5Se[M+H]+
MS2
C39H68O8Se[M+H]+
O
OO
Se
O
O
ONa
MS2
OO
SeO
Na
C18H32O3Se[M+H]+
O
OO
SeO
O
Na
C31H50O5Se[M+Na]+
OO
SeHO
Na
C21H36O3Se[M+Na]+
O
SeO
Na
O
C18H30O3Se[M+H]+
MS3
MS3
MS3
MS3
An example of the fragmentation cascade for species m/z 1013.6913 (C57H104O9Se)
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Income Received amount Stay Persons Expenses
21-02-2013 € 21 954.41 14-21 May 2015 Prof. Ricardo BentezAzevedo € 546.00
Remainingamount Prof. Zulmira Marquez
Lacava € 546.00
€ 20 862.41 Total
€ 1 092.00
Balance sheetBRASINO
EU
Our plans for the visit at the University of Brasilia
Persons Arrival DepartureAnna Flis-Borsuk - PhD studentLidia Śliwka - PhD student 1 May 2016 30 June 2016
Prof. Zbigniew FijałekProf. Piotr Suchocki 1 June 2016 30 June 2016
In May and June, I want to send two of my PhD students to Prof. Zulmira Lacava and Prof. Ricardo Azevedo, and in June I hope to come with prof. Zbigniew Fijałek for one month.
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