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Monensin A methyl ester complexes with Li + , Na + , and K + cations studied by ESI‐MS, 1 H‐ and 13 C‐NMR, FTIR, as well as PM5 semiempirical method
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.20415
Subject(s) - chemistry , intramolecular force , hydrogen bond , electrospray ionization , monensin , fourier transform infrared spectroscopy , proton nmr , metal , stoichiometry , nuclear magnetic resonance spectroscopy , crystallography , medicinal chemistry , stereochemistry , ion , molecule , organic chemistry , physics , quantum mechanics
Monensin A methyl ester (MON1) was synthesized by a new method and its ability to form complexes with Li + , Na + , and K + cations was studied by electrospray ionization–mass spectroscopy (ESI‐MS), 1 H and 13 C nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR), and PM5 semiempirical methods. It is shown that MON1 with monovalent metal cations forms stable complexes of 1:1 stoichiometry. The structures of the complexes are stabilized by intramolecular hydrogen bonds in which the OH groups are always involved. In the structure of MON1, 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 MON1 with monovalent metal cations the CO ester group is not engaged in any intramolecular hydrogen bonds. Furthermore, it is demonstrated that the strongest intramolecular hydrogen bonds are formed within the MON1–Li + complex structure. The structures of the MON1 and its complexes with Li + , Na + , and K + cations are visualized and discussed in detail. © 2005 Wiley Periodicals, Inc. Biopolymers 81: 282–294, 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