Spectroscopic, mass spectrometry, and semiempirical investigation of a new ester of Monensin A with ethylene glycol and its complexes with monovalent metal cations

Biopolymers
Adam HuczyńskiFranz Bartl

Abstract

A new ester of Monensin A with ethylene glycol (MON2) has been synthesized by a new method and its ability to form complexes with Li+, Na+, and K+ cations has been studied by ESI MS, 1H and 13C NMR, FT-IR, and PM5 semiempirical methods. It is demonstrated that MON2 forms stable complexes of 1:1 stoichiometry with monovalent metal cations. The structures of the complexes are stabilized by intramolecular hydrogen bonds in which the OH groups are always involved. In the structure of MON2 the oxygen atom of the C=O ester group is involved in very weak bifurcated intramolecular hydrogen bonds with two hydroxyl groups, whereas in the complexes of MON2 with monovalent metal cations the C=O ester group is not engaged in any intramolecular hydrogen bonds. The structures of the MON2 and its complexes with Li+, Na+, and K+ cations are visualized and discussed in detail.

References

May 7, 1990·Biochimica Et Biophysica Acta·H H MollenhauerL D Rowe
Feb 22, 2002·Rapid Communications in Mass Spectrometry : RCM·Norberto P LopesJames Staunton

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Citations

Mar 20, 2013·BioMed Research International·Daniel Aowicki, Adam Huczyński
Sep 22, 2009·Biometals : an International Journal on the Role of Metal Ions in Biology, Biochemistry, and Medicine·Ivayla N PantchevaWilliam S Sheldrick
Feb 28, 2007·Journal of Mass Spectrometry : JMS
Jul 28, 2016·Parasites & Vectors·Dietmar SteverdingAdam Huczyński

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