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

✍ Scribed by Kozyra, Kinga ;Klimek-Ochab, Magdalena ;Brzezińska-Rodak, Małgorzata ;Żymańczyk-Duda, Ewa

Book ID
120839161
Publisher
Walter de Gruyter GmbH
Year
2013
Tongue
English
Weight
621 KB
Volume
11
Category
Article
ISSN
2391-5420

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✦ Synopsis

Abstract

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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Chiral t-butylphenylphosphinothioic acid
Chiral t-butylphenylphosphinothioic acid: A useful chiral solvating agent for direct determination of enantiomeric purity of alcohols, thiols, amines, diols, aminoalcohols and related compounds
✍ Jan Omelańczuk; Marian Mikolajczyk 📂 Article 📅 1996 🏛 Elsevier Science 🌐 English ⚖ 409 KB

Enantiomers of t-butylphenylphosphinothioic acid were found to be useful chiral solvating agents (CSAs) for 1H-NMR determination of enantiomeric excess (ee) of many classes of chiral organic compounds, such as alcohols, diols, thiols, mercaptoalcohols, amines, amlnoalcohols, hydroxyacids and related