Stability study of alpha-bromophenylacetic acid: Does it represent an appropriate model analyte for chiral separations?
Popis výsledku
Identifikátory výsledku
Kód výsledku v IS VaVaI
Výsledek na webu
https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=N3bUBl-j0W
DOI - Digital Object Identifier
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Stability study of alpha-bromophenylacetic acid: Does it represent an appropriate model analyte for chiral separations?
Popis výsledku v původním jazyce
The stability of alpha-bromophenylacetic acid (BPAA) in 50% aqueous methanol solution has been tested. CE in different running buffers was used to separate BPAA from the decomposition reaction products alpha-hydroxyphenylacetic (mandelic) acid and alpha-methoxyphenylacetic acid. Suitable CE separation of all three compounds and other product, bromide, was achieved in 60 mmol/L formate buffer (pH 3.0) at -30 kV in 50 mu m (i.d.) poly(vinyl alcohol)-coated fused silica capillary (30 cm/24.5 cm) with UV detection at 200 nm. The CE method was applied to determine the reaction order of the decomposition of BPAA (0.47 mmol/L) via nucleophilic substitution in 50% aqueous methanol. The first-order reaction kinetics was confirmed by linear and non-linear regression, giving the rate constants 1.52 x 10(-4) +/- 2.76 x 10(-5)s(-1)and 7.89 x 10(-5) +/- 5.02 x 10(-6)s(-1), respectively. Additionally, the degradation products were identified by CE coupled to mass spectrometric (MS) detection. The CE-MS experiments carried out in 60 mmol/L formate buffer (pH 3.0) and in 60 mmol/L acetate buffer (pH 5.0) confirmed the results obtained by CE-UV. Furthermore, the stability of BPAA in polar solvents was tested by(1)H NMR experiments. Our results provide strong evidence of the instability and fast degradation of BPAA in 50% aqueous methanol indicating that BPAA is not suitable as the model analyte for chiral separations.
Název v anglickém jazyce
Stability study of alpha-bromophenylacetic acid: Does it represent an appropriate model analyte for chiral separations?
Popis výsledku anglicky
The stability of alpha-bromophenylacetic acid (BPAA) in 50% aqueous methanol solution has been tested. CE in different running buffers was used to separate BPAA from the decomposition reaction products alpha-hydroxyphenylacetic (mandelic) acid and alpha-methoxyphenylacetic acid. Suitable CE separation of all three compounds and other product, bromide, was achieved in 60 mmol/L formate buffer (pH 3.0) at -30 kV in 50 mu m (i.d.) poly(vinyl alcohol)-coated fused silica capillary (30 cm/24.5 cm) with UV detection at 200 nm. The CE method was applied to determine the reaction order of the decomposition of BPAA (0.47 mmol/L) via nucleophilic substitution in 50% aqueous methanol. The first-order reaction kinetics was confirmed by linear and non-linear regression, giving the rate constants 1.52 x 10(-4) +/- 2.76 x 10(-5)s(-1)and 7.89 x 10(-5) +/- 5.02 x 10(-6)s(-1), respectively. Additionally, the degradation products were identified by CE coupled to mass spectrometric (MS) detection. The CE-MS experiments carried out in 60 mmol/L formate buffer (pH 3.0) and in 60 mmol/L acetate buffer (pH 5.0) confirmed the results obtained by CE-UV. Furthermore, the stability of BPAA in polar solvents was tested by(1)H NMR experiments. Our results provide strong evidence of the instability and fast degradation of BPAA in 50% aqueous methanol indicating that BPAA is not suitable as the model analyte for chiral separations.
Klasifikace
Druh
Jimp - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
30104 - Pharmacology and pharmacy
Návaznosti výsledku
Projekt
EF15_003/0000465: Vytvoření expertního týmu pro pokročilý výzkum v separačních vědách
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
S - Specificky vyzkum na vysokych skolach
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Ostatní
Rok uplatnění
2020
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Electrophoresis
ISSN
0173-0835
e-ISSN
—
Svazek periodika
41
Číslo periodika v rámci svazku
18-19
Stát vydavatele periodika
DE - Spolková republika Německo
Počet stran výsledku
7
Strana od-do
1557-1563
Kód UT WoS článku
000552293700001
EID výsledku v databázi Scopus
2-s2.0-85088513907
Druh výsledku
Jimp - Článek v periodiku v databázi Web of Science
OECD FORD
Pharmacology and pharmacy
Rok uplatnění
2020