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Spectroscopic, mass spectrometry, and semiempirical investigation of a new ester of Monensin A with ethylene glycol and its complexes with monovalent metal cations
Author(s) -
Huczyński Adam,
Przybylski Piotr,
Brzezinski Bogumil,
Bartl Franz
Publication year - 2006
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.20502
Subject(s) - chemistry , ethylene glycol , intramolecular force , hydrogen bond , stoichiometry , metal , monensin , inorganic chemistry , molecule , organic chemistry
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, 1 H and 13 C 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 CO 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 CO 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. © 2006 Wiley Periodicals, Inc. Biopolymers 82: 491–503, 2006 This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com