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Spectroscopic, mass spectrometry and semiempirical investigation of a new 2-methoxyethyl ester of monensin A and its complexes with Li+, Na+ and K+ cations

✍ Scribed by Adam Huczyński; Daniel Łowicki; Bogumil Brzezinski; Franz Bartl

Publisher
Elsevier Science
Year
2008
Tongue
English
Weight
797 KB
Volume
874
Category
Article
ISSN
0022-2860

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✦ Synopsis

A new 2-methoxyethyl ester of monensin A (MON5) has been synthesized and its capability of complex formation with Li + , Na + and K + cations has been studied by ESI MS, 1 H and 13 C NMR, FT-IR and PM5 semiempirical methods. ESI mass spectrometry indicates that MON5 forms complexes with Li + , Na + and K + of exclusively 1:1 stoichiometry which are stable up cv = 90 V. The formation of complexes between MON5 and Na + cations is strongly favoured. Starting from cv = 110 V the fragmentation of the respective complexes is observed, primarily characterized by several dehydration steps. The structures of the MON5 complexes with Li + , Na + and K + cations are stabilized by intramolecular hydrogen bonds in which the OH groups are always involved. The structures are visualized and discussed in detail. It has been proved that the formation of a pseudo crown ring structure formed by MON5 is preferred in complexes with Na + cations.

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