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Direct determination of enantiomeric enrichment of chiral, underivatized aminophosphonic acids - useful for enantioselective bioconversion results evaluation

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Kozyra K., Klimek-Ochab M., Brzezińska-Rodak M., Żymańczyk-Duda E.
Open Chemistry
|
2013
|
vol. 11
|
issue 9
1542-1547
EN
Abstract The possibility of applying 31P NMR spectroscopy for the determination of the enantiomeric excess of the racemic mixture of non-derivatized aminophosphonic acids with small side chains has been investigated. It is proven, that the effectiveness of the application of a chiral solvating agent strongly depends on the concentration of applied shift reagent and on the pH of the particular experiment. Effectual resolution protocols are elaborated for following phosphonic acids: 1-aminoethanephosphonic acid, 1-amino-2-methylpropanephosphonic acid, 1-aminophenylmethanephosphonic acid, 1-aminophenylmethane-phosphonic acid and 1-amino-2-phenylethanephosphonic acid. Graphical abstract [...]
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